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Institute
- Institut für Chemie (3406) (remove)
Die vorliegende Arbeit beschäftigt sich mit der Synthese monodisperser, multifunktionaler Poly(amidoamine) (PAAs). Die Klasse der PAAs ist besonders interessant für eine Anwendung im Bereich der Biomedizin, da sie meist nicht toxisch ist, eine sehr geringe Immunogenizität zeigt und eine erhöhte Zellmembranpermeabilität besitzt. Allerdings ist der Einsatz linearer PAAs bisher limitiert, da ihre Synthese nur den Zugang von hoch-polydispersen Systemen mit einer streng alternierenden oder statistischen Verteilung von Funktionalitäten erlaubt. Es ist daher von großem Interesse diese Polymerklasse durch die Möglichkeit eines sequenzdefinierten Aufbaus und der Integration von neuen Funktionalitäten zu verbessern. Um dies zu ermöglichen, wurden, vergleichbar mit der etablierten Festphasensynthese von Peptiden, schrittweise funktionale Disäure- und Diamin-Bausteine an ein polymeres Träger-Harz addiert. Der sequenzielle Aufbau ermöglicht die Synthese monodisperser PAAs und die Kontrolle über die Monomersequenz. Die Wahl der Monomer-Bausteine und ihrer Funktionalitäten kann dabei für jede Addition neu getroffen werden und entscheidet so über die Sequenz der Funktionalitäten im Polymerrückgrat. Die verwendete Chemie entspricht dabei der Standardpeptidchemie, so dass mit Hilfe eines Peptidsynthese-Automaten die Synthese vollständig automatisiert werden konnte. Die Verwendung spezieller Trägerharze, die bereits mit einem synthetischen Polymerblock wie PEO oder auch mit einem Peptid vorbeladen waren, erlaubt die direkte Synthese von PEO- und Peptid-PAA Blockcopolymeren. Da die hier dargestellten PAAs später auf ihre Eignung als multivalente Polykationen in der Gentherapie getestet werden sollten, wurden zunächst Bausteine gewählt, die den Einbau verschiedener Aminfunktionalitäten ermöglichen. Die Bausteine müssen dabei so gewählt sein, dass sie kompatibel sind mit der Chemie des Peptidsynthesizers und eine quantitative Addition ohne Neben- oder Abbruchreaktionen garantieren. Darüber hinaus ist der Einbau von Peptidsequenzen und Disulfid-Einheiten in die PAA-Kette möglich, die z. B. für einen selektiven Abbau des Polymers im Organismus genutzt werden können. Zusammenfassend lässt sich feststellen, dass die in dieser Arbeit vorgestellten PAA-Systeme großes Potenzial als nicht-virale Vektoren für die Gentransfektion bieten. Sie sind nicht toxisch und zeigen Zellaufnahme-Effizienzen von bis zu 77%. Die Gentransfereffizienz ist im Vergleich zu etablierten Polymer-Vektoren zwar noch sehr gering, aber die bisherigen Versuche zeigen bereits eine mögliche Ursache, nämlich die schlechte Freisetzung des Genmaterials innerhalb der Zelle. Eine Lösung dieses Problems bietet jedoch die weitere Modifizierung der PAA-Systeme durch den Einbau von Sollbruchstellen. Diese Sollbruchstellen ermöglichen einen programmierten Abbau des Polymers innerhalb der Zelle und damit sollte die Freisetzung des Genmaterials vom Träger deutlich erleichtert werden. Mögliche Bruchstellen sind z. B. enzymatisch gezielt spaltbare Peptideinheiten oder Disulfid-Einheiten, wie sie bereits als Bausteine für die PAA-Synthese vorgestellt wurden (vergl. Kapitel 4.4). Da nur innerhalb der Zelle ein reduzierendes elektrochemisches Potential besteht, werden z. B. Disulfid-Einheiten auch nur dort gespalten und bieten außerhalb der Zelle ausreichende Stabilität zum Erhalt der Polyplexstruktur. Neben einer Anwendung in der Gentherapie bieten die hier vorgestellten PAA-Systeme den Vorteil einer systematischen Untersuchung von Struktur-Eigenschafts-Beziehungen der Polyplexe. Es wurden verschiedene Zusammenhänge zwischen der chemischen Struktur der PAA-Segmente und der Art und Stärke der DNS-Komprimierung aufgezeigt. Die Komprimierungsstärke wiederum zeigte deutlichen Einfluss auf die Internalisierungsrate und damit auch Transfektionseffizienz. Darüber hinaus zeigte sich ein drastischer Einfluss des PEO-Blocks auf die Stabilisierung der Polyplexe sowie deren intrazelluläre Freisetzung bei Zusatz von Chloroquin. Dennoch bleiben aufgrund der Komplexität der Zusammenhänge noch viele Mechanismen der Transfektion unverstanden, und es muss Aufgabe folgender Arbeiten sein, das Potential der hier eingeführten monodispersen PAA-Systeme weiter auszuloten. So wäre z. B. eine Korrelation der Kettenlänge mit den Parametern der Polyplexbildung, der Zellaufnahme und Transfektionseffizienz von großem Interesse. Darüber hinaus bietet der Einbau von Sollbruchstellen wie kurzen Peptidsequenzen oder den hier bereits eingeführten Disulfid-Einheiten neue Möglichkeiten der gezielten Freisetzung und des programmierten Abbaus, die näher untersucht werden müssen. Neben der Anwendung im Bereich der Gentransfektion sind außerdem andere Gebiete für den Einsatz von monodispersen multifunktionalen PAAs denkbar, da diese kontrollierbare und einstellbare Wechselwirkungen ermöglichen.
The properties of a series of well-defined new surfactant oligomers (dimers to tetramers)were examined. From a molecular point of view, these oligomeric surfactants consist of simple monomeric cationic surfactant fragments coupled via the hydrophilic ammonium chloride head groups by spacer groups (different in nature and length). Properties of these cationic surfactant oligomers in aqueous solution such as solubility, micellization and surface activity, micellar size and aggregation number were discussed with respect to the two new molecular variables introduced, i.e. degree of oligomerization and spacer group, in order to establish structure – property relationships. Thus, increasing the degree of oligomerization results in a pronounced decrease of the critical micellization concentration (CMC). Both reduced spacer length and increased spacer hydrophobicity lead to a decrease of the CMC, but to a lesser extent. For these particular compounds, the formed micelles are relatively small and their aggregation number decreases with increasing the degree of oligomerization, increasing spacer length and sterical hindrance. In addition, pseudo-phase diagrams were established for the dimeric surfactants in more complex systems, namely inverse microemulsions, demonstrating again the important influence of the spacer group on the surfactant behaviour. Furthermore, the influence of additives on the property profile of the dimeric compounds was examined, in order to see if the solution properties can be improved while using less material. Strong synergistic effects were observed by adding special organic salts (e.g. sodium salicylate, sodium vinyl benzoate, etc.) to the surfactant dimers in stoichiometric amounts. For such mixtures, the critical aggregation concentration is strongly shifted to lower concentration, the effect being more pronounced for dimers than for analogous monomers. A sharp decrease of the surface tension can also be attained. Many of the organic anions produce viscoelastic solutions when added to the relatively short-chain dimers in aqueous solution, as evidenced by rheological measurements. This behaviour reflects the formation of entangled wormlike micelles due to strong interactions of the anions with the cationic surfactants, decreasing the curvature of the micellar aggregates. It is found that the associative behaviour is enhanced by dimerization. For a given counterion, the spacer group may also induce a stronger viscosifying effect depending on its length and hydrophobicity. Oppositely charged surfactants were combined with the cationic dimers, too. First, some mixtures with the conventional anionic surfactant SDS revealed vesicular aggregates in solution. Also, in view of these catanionic mixtures, a novel anionic dimeric surfactant based on EDTA was synthesized and studied. The synthesis route is relatively simple and the compound exhibits particularly appealing properties such as low CMC and σCMC values, good solubilization capacity of hydrophobic probes and high tolerance to hard water. Noteworthy, mixtures with particular cationic dimers gave rise to viscous solutions, reflecting the micelle growth.
Förster Resonance Energy Transfer (FRET) plays an important role for biochemical applications such as DNA sequencing, intracellular protein-protein interactions, molecular binding studies, in vitro diagnostics and many others. For qualitative and quantitative analysis, FRET systems are usually assembled through molecular recognition of biomolecules conjugated with donor and acceptor luminophores. Lanthanide (Ln) complexes, as well as semiconductor quantum dot nanocrystals (QD), possess unique photophysical properties that make them especially suitable for applied FRET. In this work the possibility of using QD as very efficient FRET acceptors in combination with Ln complexes as donors in biochemical systems is demonstrated. The necessary theoretical and practical background of FRET, Ln complexes, QD and the applied biochemical models is outlined. In addition, scientific as well as commercial applications are presented. FRET can be used to measure structural changes or dynamics at distances ranging from approximately 1 to 10 nm. The very strong and well characterized binding process between streptavidin (Strep) and biotin (Biot) is used as a biomolecular model system. A FRET system is established by Strep conjugation with the Ln complexes and QD biotinylation. Three Ln complexes (one with Tb3+ and two with Eu3+ as central ion) are used as FRET donors. Besides the QD two further acceptors, the luminescent crosslinked protein allophycocyanin (APC) and a commercial fluorescence dye (DY633), are investigated for direct comparison. FRET is demonstrated for all donor-acceptor pairs by acceptor emission sensitization and a more than 1000-fold increase of the luminescence decay time in the case of QD reaching the hundred microsecond regime. Detailed photophysical characterization of donors and acceptors permits analysis of the bioconjugates and calculation of the FRET parameters. Extremely large Förster radii of more than 100 Å are achieved for QD as acceptors, considerably larger than for APC and DY633 (ca. 80 and 60 Å). Special attention is paid to interactions with different additives in aqueous solutions, namely borate buffer, bovine serum albumin (BSA), sodium azide and potassium fluoride (KF). A more than 10-fold limit of detection (LOD) decrease compared to the extensively characterized and frequently used donor-acceptor pair of Europium tris(bipyridine) (Eu-TBP) and APC is demonstrated for the FRET system, consisting of the Tb complex and QD. A sub-picomolar LOD for QD is achieved with this system in azide free borate buffer (pH 8.3) containing 2 % BSA and 0.5 M KF. In order to transfer the Strep-Biot model system to a real-life in vitro diagnostic application, two kinds of imunnoassays are investigated using human chorionic gonadotropin (HCG) as analyte. HCG itself, as well as two monoclonal anti-HCG mouse-IgG (immunoglobulin G) antibodies are labeled with the Tb complex and QD, respectively. Although no sufficient evidence for FRET can be found for a sandwich assay, FRET becomes obvious in a direct HCG-IgG assay showing the feasibility of using the Ln-QD donor-acceptor pair as highly sensitive analytical tool for in vitro diagnostics.
Polyelectrolyte microcapsules containing stimuli-responsive polymers have potential applications in the fields of sensors or actuators, stimulable microcontainers and controlled drug delivery. Such capsules were prepared, with the focus on pH-sensitivity and carbohydrate-sensing. First, pH-responsive polyelectrolyte capsules were produced by means of electrostatic layer-by-layer assembly of oppositely charged weak polyelectrolytes onto colloidal templates that were subsequently removed. The capsules were composed of poly(allylamine hydrochloride) (PAH) and poly(methacrylic acid) (PMA) or poly(4-vinylpyridine) (P4VP) and PMA and varied considerably in their hydrophobicity and the influence of secondary interactions. These polymers were assembled onto CaCO3 and SiO2 particles with diameters of ~ 5 µm, and a new method for the removal of the silica template under mild conditions was proposed. The pH-dependent stability of PAH/PMA and P4VP/PMA capsules was studied by confocal laser scanning microscopy (CLSM). They were stable over a wide pH-range and exhibited a pronounced swelling at the edges of stability, which was attributed to uncompensated positive or negative charges within the multilayers. The swollen state could be stabilized when the electrostatic repulsion was counteracted by hydrogen-bonding, hydrophobic interactions or polymeric entanglement. This stabilization made it possible to reversibly swell and shrink the capsules by tuning the pH of the solution. The pH-dependent ionization degree of PMA was used to modulate the binding of calcium ions. In addition to the pH-sensitivity, the stability and the swelling degree of these capsules at a given pH could be modified, when the ionic strength of the medium was altered. The reversible swelling was accompanied by reversible permeability changes for low and high molecular weight substances. The permeability for glucose was evaluated by studying the time-dependence of the buckling of the capsule walls in glucose solutions and the reversible permeability modulation was used for the encapsulation of polymeric material. A theoretical model was proposed to explain the pH-dependent size variations that took into account an osmotic expanding force and an elastic restoring force to evaluate the pH-dependent size changes of weak polyelectrolyte capsules. Second, sugar-sensitive multilayers were assembled using the reversible covalent ester formation between the polysaccharide mannan and phenylboronic acid moieties that were grafted onto poly(acrylic acid) (PAA). The resulting multilayer films were sensitive to several carbohydrates, showing the highest sensitivity to fructose. The response to carbohydrates resulted from the competitive binding of small molecular weight sugars and mannan to the boronic acid groups within the film, and was observed as a fast dissolution of the multilayers, when they were brought into contact with the sugar-containing solution above a critical concentration. It was also possible to prepare carbohydrate-sensitive multilayer capsules, and their sugar-dependent stability was investigated by following the release of encapsulated rhodamine-labeled bovine serum albumin (TRITC-BSA).
First studies of electron transfer in [N]phenylenes were performed in bimolecular quenching reactions of angular [3]- and triangular [4]phenylene with various electron acceptors. The relation between the quenching rate constants kq and the free energy change of the electron transfer (ΔG0CS ) could be described by the Rehm-Weller equation. From the experimental results, a reorganization energy λ of 0.7 eV was derived. Intramolecular electron transfer reactions were studied in an [N]phenylene bichomophore and a corresponding reference compound. Fluorescence lifetime and quantum yield of the bichromophor display a characteristic dependence on the solvent polarity, whereas the corresponding values of the reference compound remain constant. From the results, a nearly isoenergonic ΔG0CS can be determined. As the triplet quantum yield is nearly independent of the polarity, charge recombination leads to the population of the triplet state.
Pestizideinsatz gegen die Rosskastanien-Miniermotte (Cameraria ohridella) im Stadtgebiet Potsdam
(2005)
In Deutschland hat sich in den letzten zehn Jahren die aus dem Balkan eingewanderte Rosskastanien-Miniermotte verbreitet; sie richtet vor allem in Ballungsgebieten an der weiß blühenden Rosskastanie starke Schäden an. Neben der vollständigen mechanischen Beseitigung und Entsorgung des Falllaubes im Herbst eignen sich zur Bekämpfung chemische Pflanzenschutzmittel. In Potsdam sind 2001 und 2003 an zwei Standorten befallene Rosskastanien versuchsweise mit zwei unterschiedlichen Pestiziden erfolgreich behandelt worden. 2005 wurden die Standorte beprobt und die Bodenproben auf Rückstände der verwendeten Mittel untersucht. TerraTech möchte Kommunen mit vergleichbarem Problem Hinweise auf Bekämpfungsmethoden geben, veröffentlicht diesen Beitrag aber vor allem unter dem Gesichtspunkt des Boden- und Grundwasserschutzes.
Die Anwendung zweier ähnlicher fasergekoppelte Diodenlaser-Spektrometer-Systeme werden vorgestellt. Basis sind handelsübliche DFB-Laserdioden der optischen Kommunikationstechnik. Der faseroptische Aufbau, das Detektionsverfahren (2f Wellenlängenmodulations-Spektroskopie mit Balanced Receiver), Rauschverhalten und Detektionslimit werden diskutiert. Zur in-situ Plasma-Diagnostik von CO- und CO2-Konzentrationen in industriellen CO2-Lasern der Materialbearbeitung wurde eine Wellenlänge von 1582 nm verwendet. Bei einem Gasdruck von 100 hPa und einer Absorptionsweglänge von 14,9 cm wurden mit einer Laserdiode simultan CO- und CO2-Konzentrationen von 0% bis 11% im Gasgefäß bei laufender Hochfrequenzgasentladung des CO2-Lasers zeitaufgelöst gemessen. Vorgestellt und diskutiert werden Aufbau und Eigenschaften des Spektrometers sowie die Ergebnisse der dynamischen Gasanalysen, die zu einer Verbesserung der Katalysator-Technik im CO2-Laser beigetragen haben.Mit isotopenaufgelöster CO- und CO2-Spektroskopie können biologische Gasaustauschprozesse, z.B. in Gasen aus dem Erdboden untersucht werden. Hierzu wurde ein fasergekoppeltes feldtaugliches Diodenlaser-Spektrometer bei Wellenlängen um 1605 nm zur Messungder Isotopologe 12C16O, 13C16O, 12C18O und 12C16O2, 13C16O2, 12C18O16O aufgebaut. Die Messung erfolgt extraktiv in Langwegzellen mit unterschiedlichen Absorptionsweglängen von 100.9 m und 29.9 m. Es werden Kalibrationsmessungen zur Linearität und zur Präzision der Bestimmung der Isotopenverhältnisse sowie Wiederholungsmessungen zur Stabilität vorgestellt. Nachweisgrenzen von wenigen ppm konnten für die CO- und CO2-Isotopologen erhalten werden.
The fluorescence properties and the fluorescence quenching by Tb3+ of substituted benzoic acid were investigated in solution at different pH. The substituted benzoic acids were used as simple model compounds for chromophores present in humic substances (HS). It is shown that the fluorescence properties of the model compounds resemble fluorescence of HS quite well. A major factor determining the fluorescence of model compounds are proton transfer reactions in the electronically excited state. It is intriguing that the fluorescence of the model compounds was almost not quenched by Tb3+ while the HS fluorescence was decreased very effectively. From our results we concluded that proton transfer reactions as well as conformational reorientation processes play an important role in the fluorescence of HS. The luminescence of bound Tb3+ was sensitized by an energy transfer step upon excitation of the model compounds and of HS, respectively. For HS the observed sensitization was dependent on its origin indicating differences 1) in the connection between chromophores and binding sites and 2) in the energy levels of the chromophore triplet states. Hence, the observed sensitization of the Tb3+ luminescence could be useful to characterize structural differences of HS in solution. Interlanthanide energy transfer between Tb3+ and Nd3+ was used to determine the average distance R between both ions using the well-known formalism of luminescence resonance energy transfer. R was dependent on the origin of the HS reflecting the difference in structure. The value of Rmin seemed to be a unique feature of the HS. It was further found that upon variation of the pH R also changed. This demonstrates that the measurement of interlanthanide energy transfer can be used as a direct method to monitor conformational changes in HS.
The formation of colloids by the controlled reduction, nucleation, and growth of inorganic precursor salts in different media has been investigated for more than a century. Recently, the preparation of ultrafine particles has received much attention since they can offer highly promising and novel options for a wide range of technical applications (nanotechnology, electrooptical devices, pharmaceutics, etc). The interest derives from the well-known fact that properties of advanced materials are critically dependent on the microstructure of the sample. Control of size, size distribution and morphology of the individual grains or crystallites is of the utmost importance in order to obtain the material characteristics desired. Several methods can be employed for the synthesis of nanoparticles. On the one hand, the reduction can occur in diluted aqueous or alcoholic solutions. On the other hand, the reduction process can be realized in a template phase, e.g. in well-defined microemulsion droplets. However, the stability of the nanoparticles formed mainly depends on their surface charge and it can be influenced with some added protective components. Quite different types of polymers, including polyelectrolytes and amphiphilic block copolymers, can for instance be used as protecting agents. The reduction and stabilization of metal colloids in aqueous solution by adding self-synthesized hydrophobically modified polyelectrolytes were studied in much more details. The polymers used are hydrophobically modified derivatives of poly(sodium acrylate) and of maleamic acid copolymers as well as the commercially available branched poly(ethyleneimine). The first notable result is that the polyelectrolytes used can act alone as both reducing and stabilizing agent for the preparation of gold nanoparticles. The investigation was then focused on the influence of the hydrophobic substitution of the polymer backbone on the reduction and stabilization processes. First of all, the polymers were added at room temperature and the reduction process was investigated over a longer time period (up to 8 days). In comparison, the reduction process was realized faster at higher temperature, i.e. 100°C. In both cases metal nanoparticles of colloidal dimensions can be produced. However, the size and shape of the individual nanoparticles mainly depends on the polymer added and the temperature procedure used. In a second part, the influence of the prior mentioned polyelectrolytes was investigated on the phase behaviour as well as on the properties of the inverse micellar region (L2 phase) of quaternary systems consisting of a surfactant, toluene-pentanol (1:1) and water. The majority of the present work has been made with the anionic surfactant sodium dodecylsulfate (SDS) and the cationic surfactant cetyltrimethylammonium bromide (CTAB) since they can interact with the oppositely charged polyelectrolytes and the microemulsions formed using these surfactants present a large water-in-oil region. Subsequently, the polymer-modified microemulsions were used as new templates for the synthesis of inorganic particles, ranging from metals to complex crystallites, of very small size. The water droplets can indeed act as nanoreactors for the nucleation and growth of the particles, and the added polymer can influence the droplet size, the droplet-droplet interactions, as well as the stability of the surfactant film by the formation of polymer-surfactant complexes. One further advantage of the polymer-modified microemulsions is the possibility to stabilize the primary formed nanoparticles via a polymer adsorption (steric and/or electrostatic stabilization). Thus, the polyelectrolyte-modified nanoparticles formed can be redispersed without flocculation after solvent evaporation.
Chitin ist ein Polysaccharid, welches aus N-Acetylglucosamin (GlcNAc) aufgebaut ist. Das Biopolymer kommt in der Natur in Invertebraten, Algen, Pilzen und Einzellern vor. Chitinasen hydrolysieren Chitin. Diese Enzyme sind essentiell für die Regulierung und Entwicklung von Arthropoden und Mikroorganismen. Sie fungieren in Pflanzen als Phytoalexine. Das verstärkt das Interesse am Design neuer natürlicher und synthetischer Chitinase-inhibitoren, die als potentielle Insektizide, Fungizide, Antimalaria bzw. Antiasthmatika eingesetzt werden können. Ziel dieser Arbeit war die Synthese von neuen Thioglycosidanaloga von N-Acetyl-chitooligosacchariden und deren Untersuchung als Enzyminhibitoren. Die geschützten 4-O-Tf-galactopyranosylthioglycoside wurden aus den korrespondierenden p-Methoxyphenylglycosiden von GlcNAc nach einer neuen Methode in einer Stufe hergestellt. Die Reaktion der galacto-Triflate mit 2-Acetamido-3,4,6-tri-O-acetyl-2-desoxy-1-thio-ß-D-glucopyranose in Gegenwart von Natriumhydrid und 15-Krone-5 in THF lieferte die Pseudo-Trisaccharide. Die Herstellung der Glycosyl-Thiazoline aus den entsprechenden p-Methoxyphenyl-glycosiden mit Lawesson's Reagenz ist nach einem neuen Reaktionsweg beschrieben wie auch die Synthese der Thioacetamide von GlcNAc-Oligomeren. Die Pseudo-Oligosaccharide wurden als Inhibitoren der Chitinasen von Serratia marcescens, Chironomus tentans, Acanthocheilonema viteae und Hevaea brasiliensis sowie der N-Acetyl-glucosaminidase von Chironomus tentans getestet. In einigen Fällen ergab sich eine Hemmung (IC50) im µM-Bereich.
Es wurden Poly(2-isopropyl-2-oxazolin)-Makroinitiatoren mit terminaler Ammoniumtrifluoracetat-Endgruppe synthetisiert, die anschließend für die Ammonium vermittelte NCA Polymerisation in NMP eingesetzt wurden. Die hierbei synthetisierten Poly(2-isopropyl-2-oxazolin)-block-poly(L-glutamat) (PIPOX-PEP) Blockcopolymere hatten eine Molekulargewichtsverteilung von 1,2 (UZ). Es wurde beobachtet, dass Poly(2-isopropyl-2-oxazolin) bei langen Zeiten oberhalb der LCST irreversibel sphärische Strukturen bildet, die eine hierarchische Struktur besitzen und bei denen es sich möglicherweise um "large compound micelles" handelt. PIPOX-PEP kann in wässeriger Lösung bei langen Zeiten oberhalb der LCST "cottonball" Strukturen bilden. Die Aggregate wurden mittels Lichtstreuung, NMR und TEM charakterisiert. Im Rahmen der Arbeit wurden Strukturbildungsmodelle entwickelt.
Bioorganisch-synthetische Blockcopolymere sind sowohl für die Materialwissenschaft als auch für die Medizin hochinteressant. Diese Arbeit beschäftigte sich mit neuen Synthesewegen für die Herstellung dieser Blockcopolymere. Zunächst wurde der klassische Ansatz zur Herstellung eines Blockcopolymers über die Kupplung der beiden Segmente aufgegriffen. Hierzu wurde eine Methode zur Synthese von selektiv säureendfunktionalisierten Polyacrylaten mittels einer terminalen Benzylesterschutzgruppe vorgestellt. Für die Herstellung von bioorganisch-synthetischen Blockcopolymeren mit einem größeren Polymersegment wurde daher ein anderer Syntheseansatz entwickelt. Dieser geht von einem funktionalisierten Oligopeptid aus, an dem durch Polymerisation das synthetische Segment aufgebaut wird. Der Aufbau erfolgte durch kontrolliert radikalische Polymerisation, um ein möglichst definiertes Segment zu erhalten. Zunächst wurde eine Synthese von Oligopeptid-Makroinitiatoren für die ATRP-Polymerisation durchgeführt. Es konnte gezeigt werden, dass in geeigneten polaren Lösungsmitteln (DMSO, DMF) eine Polymerisation mit dem ATRP-Oligopeptid-Makroinitiator erfolgreich ist. Allerdings treten während der Polymerisation Wechselwirkungen zwischen dem Katalysator und dem Oligopeptid auf. Eine Alternative bietet die RAFT-Polymerisation, da sie ohne einen Katalysator durchgeführt wird. Es gelang ausgehend von dem Oligopeptid-ATRP-Makroinitiator den Überträger herzustellen. Die RAFT-Polymerisation mit einem Oligopeptidüberträger stellt eine wichtige Methode für die Herstellung von bioorganisch-synthetischen Blockcopolymeren dar. Sie besitzt eine hohe Toleranz gegenüber funktionellen Gruppen. Die so hergestellten Blockcopolymere sind frei von Verunreinigungen, wie z.B. Übergangsmetallen. Dabei läßt sich das Molekulargewicht des synthetischen Blocks bei einer Polydispersität um 1,2 gut kontrollieren.
Nonaqueous synthesis of metal oxide nanoparticles and their assembly into mesoporous materials
(2006)
This thesis mainly consist of two parts, the synthesis of several kinds of technologically interesting crystalline metal oxide nanoparticles via nonaqueous sol-gel process and the formation of mesoporous metal oxides using some of these nanoparticles as building blocks via evaporation induced self-assembly (EISA) technique. In the first part, the experimental procedures and characterization results of successful syntheses of crystalline tin oxide and tin doped indium oxide (ITO) nanoparticles are reported. SnO2 nanoparticles exhibit monodisperse particle size (3.5 nm in average), high crystallinity and particularly high dispersibility in THF, which enable them to become the ideal particulate precursor for the formation of mesoporous SnO2. ITO nanoparticles possess uniform particle morphology, narrow particle size distribution (5-10 nm), high crystallinity as well as high electrical conductivity. The synthesis approaches and characterization of various mesoporous metal oxides, including TiO2, SnO2, mixture of CeO2 and TiO2, mixture of BaTiO3 and SnO2, are reported in the second part of this thesis. Mesoporous TiO2 and SnO2 are presented as highlights of this part. Mesoporous TiO2 was produced in the forms of both films and bulk material. In the case of mesoporous SnO2, the study was focused on the high order of the porous structure. All these mesoporous metal oxides show high crystallinity, high surface area and rather monodisperse pore sizes, which demonstrate the validity of EISA process and the usage of preformed crystalline nanoparticles as nanobuilding blocks (NBBs) to produce mesoporous metal oxides.
In this work approaches for new detection system development for an Analytical Ultracentrifuge (AUC) were explored. Unlike its counterpart in chromatography fractionation techniques, the use of a Multidetection system for AUC has not yet been implemented to full extent despite its potential benefit. In this study we tried to couple existing fundamental spectroscopic and scattering techniques that are used in day to day science as tool for extracting analyte information. Trials were performed for adapting Raman, Light scattering and UV/Vis (with possibility to work with the whole range of wavelengths) to AUC. Conclusions were drawn for Raman and Light scattering to be a possible detection system for AUC, while the development for a fast fiber optics based multiwavelength detector was completed. The multiwavelength detector demonstrated the capability of data generation matching the literature and reference measurement data and faster data collection than that of the commercial instrument. It became obvious that with the generation of data in 3-D space in the UV/Vis detection system, the user can select the wavelength for the evaluation of experimental results as the data set contains the whole range of information from UV/Vis wavelength. The detector showed the data generation with much faster speed unlike the commercial instruments. The advantage of fast data generation was exemplified with the evaluation of data for a mixture of three colloids. These data were in conformity with measurement results from normal radial experiments and without significant diffusion broadening. Thus conclusions were drawn that with our designed Multiwavelength detector, meaningful data in 3-D space can be collected with much faster speed of data generation.
Retrosynthese von Perlmutt
(2006)
In dieser Arbeit ist es gelungen, die Bedeutung physikalisch-chemischer Mechanismen in der Biomineralisation gegenüber der bisher angenommenen Dominanz spezifischer biomolekularer Erkennungsmechanismen aufzuzeigen. Dazu wurden drei Ansätze verfolgt: Zum einen wurden Studien zur Calciumcarbonatkristallisation durchgeführt. Zum anderen wurde das Biomineral Perlmutt intensiv untersucht. Als drittes wurde ein Modellsystem entwickelt, mit dem künstliches Perlmutt synthetisiert und ein Mechanismus für die Perlmuttmineralisation vorgeschlagen werden konnte. Im ersten Schritt wurden in einem simplen Kristallisationsansatz komplexe Calciumcarbonatüberstrukturen ohne die Verwendung von Additiven synthetisiert. Es wurde gezeigt, daß diese durch orientierte Anlagerung von Nanopartikeln gebildet werden, bei der dipolare Felder eine wichtige Rolle zu spielen scheinen. Dieser Mechansimus war bislang für Calciumcarbonat unbekannt und ermöglicht die Synthese komplexer Kristallmorphologien, wodurch die Frage aufgeworfen wird, ob er bei der Biomineralbildung von Bedeutung sein kann. Durch Einsatz minimaler Mengen eines einfachen, synthetischen Additivs bei der Kristallisation wurden zu Überstrukturen angeordnete Aragonitplättchen synthetisiert, die von einer wenige nm dicken Schicht aus amorphen Calciumcarbonat umgeben sind. Eine solche Schicht wurde auch bei den Aragonitplättchen Perlmutts entdeckt (s.u.) und bietet möglicherweise in verschiedenen Systemen eine Erklärung für die Stabilisierung der sonst metastabilen Aragonitphase. Im zweiten Schritt wurden bei der Untersuchung von natürlichem Perlmutt zwei bislang unbekannte Strukturmerkmale entdeckt: Es gibt Bereiche, die nicht aus den charakteristischen Plättchen bestehen, sondern wesentlich weniger stark mineralisert sind. Die Mineralphase besteht in diesen Bereichen aus Nanopartikeln. Es wurde weiterhin gezeigt, daß die Aragonitplättchen von einer wenige nm dicken Schicht aus amorphem Calciumcarbonat umgeben ist. Die gängigen Modelle der Perlmuttbildung sind mit diesen Beobachtungen nicht zu vereinbaren und somit zu hinterfragen. Dagegen deuten diese Ergebnisse ein Wachstum von Perlmutt über ACC-Nanopartikel an. Unter der Annahme der Bedeutung physikalisch-chemischer Mechanismen in der Biomineralisation wurde schließlich als dritter Schritt ein Ansatz zur in vitro-Retrosynthese von Biomineralien ausgehend von ihrer unlöslichen Matrix entwickelt. Mit diesem Ansatz ist es erstmals gelungen, künstliches Perlmutt auf synthetischem Wege herzustellen, das morphologisch nicht vom Original zu unterscheiden ist. Die existierenden Unterschiede konnten zeigen, daß der Mineralisationsprozeß nicht auf ein spezifisches Mikroumgebungssystem beschränkt, sondern "allgemeiner gültig"' sein muß. Bei der Retrosynthese gibt es zwei Schlüsselfaktoren: Zum einen die demineralisierte unlösliche Perlmuttmatrix als dreidimensionales Gerüst für das künstliche Perlmutt, zum anderen amorphe Precursorpartikel, die die Mineralphase bilden. Es werden keinerlei Proteine oder andere Biomoleküle verwendet. Dieser Ansatz bietet die Möglichkeit, den Mineralisationsprozeß an einem in vitro-Modellsystem zu verfolgen, was für das in vivo-System, wenn überhaupt, nur unter starken Einschränkungen möglich ist. Es wurde gezeigt, daß das künstliche Perlmutt über die Mesoskalentransformation von ACC-Precursorn innerhalb der Matrix gebildet wird und als möglicher Mechanismus bei der Biomineralisation von natürlichem Perlmutt diskutiert. Es konnte in der vorliegenden Arbeit konsequent gezeigt werden, daß die Imitation von Biomineralisationsprozessen in in vitro-Ansätzen möglich ist, wobei chemisch-physikalische Parameter dominieren. In zukünftigen Studien sollten einerseits die mechanischen Eigenschaften des künstlichen Perlmutts untersucht werden, wofür sich in Vorversuchen im Rahmen dieser Arbeit die Nanoindentierung als geeignet herausgestellt hat. Es sollte geprüft werden, ob das hier ermittelte Prinzip zur Mineralisierung in der Materialentwicklung angewendet werden kann. Andererseits sollte die Retrosynthese auf andere Systeme ausgeweitet und in vivo-Studien durchgeführt werden, um die Gültigkeit der vorgeschlagenen Mechanismen zu überprüfen.
Ultrathin, semi-permeable membranes are not only essential in natural systems (membranes of cells or organelles) but they are also important for applications (separation, filtering) in miniaturized devices. Membranes, integrated as diffusion barriers or filters in micron scale devices need to fulfill equivalent requirements as the natural systems, in particular mechanical stability and functionality (e.g. permeability), while being only tens of nm in thickness to allow fast diffusion times. Promising candidates for such membranes are polyelectrolyte multilayers, which were found to be mechanically stable, and variable in functionality. In this thesis two concepts to integrate such membranes in larger scale structures were developed. The first is based on the directed adhesion of polyelectrolyte hollow microcapsules. As a result, arrays of capsules were created. These can be useful for combinatorial chemistry or sensing. This concept was expanded to couple encapsulated living cells to the surface. The second concept is the transfer of flat freestanding multilayer membranes to structured surfaces. We have developed a method that allows us to couple mm2 areas of defect free film with thicknesses down to 50 nm to structured surfaces and to avoid crumpling of the membrane. We could again use this technique to produce arrays of micron size. The freestanding membrane is a diffusion barrier for high molecular weight molecules, while small molecules can pass through the membrane and thus allows us to sense solution properties. We have shown also that osmotic pressures lead to membrane deflection. That could be described quantitatively.
Der Adhäsionsprozess an Cellulosefasern sollte bis hin zur molekularen Ebene aufgeklärt werden. Zuerst wurde eine definierte Celluloseoberfläche durch Aufschleudern hergestellt und eingehend charakterisiert wurde. Die Beschaffenheit der Oberfläche ist stark abhängig von der Konzentration Celluloselösung, die für das Aufschleudern benutzt wurde. Für geringe Konzentrationen bildete sich ein Netzwerk von Cellulosefibrillen über die Siliziumoberfläche aus. In einem mittleren Bereich wurden geschlossene Filme mit Dicken zwischen 1,5 und ca. 10 nm erhalten. Diese Filme wiesen eine Rauhigkeit unter 2 nm auf, was der Größe eines Cellulosemoleküls entspräche. Mit höheren Konzentrationen wurden die Filme dicker und auch rauer. Die molekular glatten Cellulosefilme wurden zur Untersuchung der Adhäsionseigenschaften zwischen Celluloseoberflächen und ihrer Modifikation durch den Einfluss von Haftvermittlern (Polyelektrolyte) eingesetzt. Dafür wurde das Haftungsvermögen von Celluloseperlen auf der glatten Celluloseoberfläche analysiert. Die Adhäsion der Celluloseperlen hängt dabei von der Menge und von der Art des adsorbierten Polyelektrolyts ab. Geringe Polyelektrolytkonzentrationen ermöglichen wegen der teilweisen Bedeckung der Celluloseoberflächen eine Verstärkung der Haftvermittlung (Adhäsion). Höhere Konzentrationen an Polyelektrolyten bedecken die Celluloseoberfläche komplett, so dass die Symmetrie der Polyelektrolytadsorption entscheidend wird. Wenn Celluloseperlen und glatte Celluloseoberfläche gleichzeitig mit Polyelektrolyten beschichtet werden verringert sich bei hohen Konzentrationen die Adhäsion erheblich. Ein hohes Maß an Adhäsion wird dagegen erreicht, wenn nur eine der beiden gegenüberliegende Celluloseoberflächen separat beschichtet und dann in Kontakt mit der anderen gebracht Oberfläche wurde. Der Einfluss einer äußeren Kraft auf die haftenden Celluloseperlen wurde untersucht, um eine Aussage über die auftretenden Adhäsionskräfte machen zu können. Dafür wurde eine spezielle Strömungszelle entwickelt, mit der die Bewegung von Celluloseperlen beobachtet werden kann. Je nach Ausrichtung der Strömungszelle bewegten sich die Celluloseperlen unterschiedlich schnell. War die Strömungszelle horizontal ausgerichtet, wirkte zusätzlich zur Adhäsionskraft noch die Gravitation auf die Oberfläche, so dass hier eine wesentlich langsamere Durchschnittsgeschwindigkeit ermittelt wurde als für die Messungen in vertikaler Ausrichtung. Die Zugabe von verschiedenen Polyelektrolyten bei den Messungen mit der Strömungszelle hatte einen erheblichen Einfluss auf die Beweglichkeit der haftenden Celluloseperlen. Bei geringen Polyelektrolytkonzentrationen wurde das Potential der einzelnen Polyelektrolyten zur effektiven Haftvermittlung durch eine signifikant geringere Durchschnittsgeschwindigkeit der rollenden Celluloseperlen sichtbar. Aus der kritischen Anfangsgeschwindigkeit der rollenden Celluloseperlen wurde die Adhäsionsarbeit errechnet, die für die Bewegung nötig ist.
Die Beeinflussung optischer Eigenschaften durch Bestrahlung stellt eine Grundlage für die Herstellung anisotroper optischer Komponenten dar. In dünnen Schichten von Azobenzen-Polymeren kann optische Anisotropie durch linear polarisierte Bestrahlung induziert oder modifiziert werden. Ziel der Arbeit war es, wesentliche Struktur-Eigenschafts-Beziehungen zum Prozess der Photoorientierung zu erarbeiten, um so eine Optimierung der Materialien für verschiedene Anwendungen ermöglichen. In isotropen Schichten flüssigkristalliner und amorpher Azobenzen-Polymeren wird das Ausmaß der induzierten optischen Anisotropie günstig durch eine Donor/Akzeptor-Substitution in 4,4'-Position beeinflusst. Die Induktionsgeschwindigkeit ist in Schichten flüssigkristalliner Polymeren deutlich geringer, jedoch lassen sich höhere Werte der Doppelbrechung und des Dichroismus erreichen. In Copolymeren bewirkt die Photoorientierung der Azobenzen-Seitengruppen eine kooperative Orientierung von formanisotropen Seitengruppen. Die Mesogenität der nicht-photochromen Seitengruppen erhöht das Ausmaß der induzierten optischen Anisotropie. Die Stabilität der induzierten Doppelbrechung und des Dichroismus wird durch diese Gruppen gesteigert. In Schichten flüssigkristalliner Polymeren wird die induzierte optische Anisotropie beim Tempern im Bereich der Mesophasen erheblich verstärkt. Dabei reicht ein geringes Maß an induzierter Anisotropie aus, um Doppelbrechungs- und Dichroismuswerte zu erzielen, wie sie für LC-Domänen typisch sind. In orientierten Schichten von Azobenzen-Polymeren wird das Resultat der linear polarisierten Bestrahlung durch die Stärke der anisotropen Wechselwirkungen in den flüssigkristallinen Domänen oder den LB-Multilayern bestimmt. Eine lichtinduzierte Reorientierung kann nur erreicht werden, wenn diese Wechselwirkungen überwunden werden können. Erfolgt eine Photoreorientierung in den orientierten Polymerschichten, werden in Copolymeren formanisotrope Seitengruppen ebenfalls kooperativ reorientiert. Eine vorgelagerte UV-Bestrahlung kann durch Erzeugung eines hohen Anteils an nicht-mesogenen Z-Isomeren die anisotropen Wechselwirkungen stark schwächen und so die Seitengruppen entkoppeln. Aus diesem Zustand erfolgt die Photoreorientierung mit einer der Photoorientierung in isotropen Schichten vergleichbaren Effizienz. Die erarbeiteten Struktur-Eigenschafts-Beziehungen liefern einen Beitrag zur Optimierung derartiger Materialien für Anwendungen in den Bereichen optischer Funktionsschichten, holographischer Datenspeicherung oder der Generierung von Oberflächenreliefgittern.
In recent years, the aim of supramolecular syntheses is not only the creation of particular structures but also the introduction of specific functions in these supramolecules. The present work describes the use of the ionic self-assembly (ISA) route to generate nanostructured materials with integrated functionality. Since the ISA strategy has proved to be a facile method for the production of liquid-crystalline materials, we investigated the phase behaviour, physical properties and function of a variety of ISA materials comprising a perylene derivative as the employed oligoelectrolyte. Functionality was introduced into the materials through the use of functional surfactants. In order to meet the requirements to produce functional ISA materials through the use of functional surfactants, we designed and synthesized pyrrole-derived monomers as surfactant building blocks. Owing to the presence of the pyrrole moiety, these surfactants are not only polymerizable but are also potentially conductive when polymerized. We adopted single-tailed and double-tailed N-substituted pyrrole monomers as target molecules. Since routine characterization analysis of the double-tailed pyrrole-containing surfactant indicated very interesting, complex phase behaviour, a comprehensive investigation of its interfacial properties and mesophase behavior was conducted. The synthesized pyrrole-derived surfactants were then employed in the synthesis of ISA complexes. The self-assembled materials were characterized and subsequently polymerized by both chemical and electrochemical methods. The changes in the structure and properties of the materials caused by the in-situ polymerization were addressed. In the second part of this work, the motif investigated was a property rather than a function. Since chiral superstructures have obtained much attention during the last few years, we investigated the possibility of chiral ISA materials through the use of chiral surfactants. Thus, the work involved synthesis of novel chiral surfactants and their incorporation in ISA materials with the aim of obtaining ionically self-assembled chiral superstructures. The results and insights presented here suggest that the presented synthesis strategy can be easily extended to incorporate any kind of charged tectonic unit with desired optical, electrical, or magnetic properties into supramolecular assemblies for practical applications.
Neolignans, dehydrodimers of phenylpropenes, are natural products that exhibit different biological activities. 8,5’-Neolignans containing a trans- dihydrobenzofuran skeleton are the most abundant neolignans in nature. The published syntheses of trans-dihydrobenzofurans are multistep procedures that are time consuming and provide the product in low yield. Furthermore, all dimerisation reactions either in the presence of enzymes or mediated by metal salts are yielding dimers consisting of two units of the same phenylpropene compound, narrowing substantially the substitution pattern. Two different general synthetic approaches were examined. The first strategy was the enantioselective deprotonation at the α-carbon of the ο-alkyl phenols in the presence of a chiral diamine and sBuLi. Synthesis of several new phosphorous-based directed ortho-metalation groups was studied. The examined compounds having these new groups decomposed even under very mild reaction conditions and are not suitable for the application in the synthesis. The second strategy was to examine one [3+2] cycloaddition reaction, transition metal catalysed Heck oxyarylation reaction, in the synthetic approach to compounds having trans-dihydrobenzofuran skeleton. Palladium catalysed Heck oxyarylation reaction with halogenophenols or ortho-diazonium phenols as the starting material allowed the trans-dihydrobenzofuran compounds as the major products in acceptable yield and in one step. The products were formed under ligand free condition, as well as in the presence of some strong coordinating ligands (Ph3P). The experiments with several chiral ligands, showed that the obtained trans-dihydrobenzofurans were racemic mixtures. This result suggests formation of an achiral intermediate along the reaction pathway, which causes the lack of stereoselectivity in the products. Initially formed trans-dihydrobenzofuran compounds are the key precursors of many naturally occurring neolignans, and can be easily converted to 8,5’-neolignan derivatives.
Adsorption layers of soluble surfactants enable and govern a variety of phenomena in surface and colloidal sciences, such as foams. The ability of a surfactant solution to form wet foam lamellae is governed by the surface dilatational rheology. Only systems having a non-vanishing imaginary part in their surface dilatational modulus, E, are able to form wet foams. The aim of this thesis is to illuminate the dissipative processes that give rise to the imaginary part of the modulus. There are two controversial models discussed in the literature. The reorientation model assumes that the surfactants adsorb in two distinct states, differing in their orientation. This model is able to describe the frequency dependence of the modulus E. However, it assumes reorientation dynamics in the millisecond time regime. In order to assess this model, we designed a SHG pump-probe experiment that addresses the orientation dynamics. Results obtained reveal that the orientation dynamics occur in the picosecond time regime, being in strong contradiction with the two states model. The second model regards the interface as an interphase. The adsorption layer consists of a topmost monolayer and an adjacent sublayer. The dissipative process is due to the molecular exchange between both layers. The assessment of this model required the design of an experiment that discriminates between the surface compositional term and the sublayer contribution. Such an experiment has been successfully designed and results on elastic and viscoelastic surfactant provided evidence for the correctness of the model. Because of its inherent surface specificity, surface SHG is a powerful analytical tool that can be used to gain information on molecular dynamics and reorganization of soluble surfactants. They are central elements of both experiments. However, they impose several structural elements of the model system. During the course of this thesis, a proper model system has been identified and characterized. The combination of several linear and nonlinear optical techniques, allowed for a detailed picture of the interfacial architecture of these surfactants.
The Reversible Addition Fragmentation Chain Transfer (RAFT) process using the new RAFT agent benzyldithiophenyl acetate is shown to be a powerful polymerization tool to synthesize novel well-defined amphiphilic diblock copolymers composed of the constant hydrophobic block poly(butyl acrylate) and of 6 different hydrophilic blocks with various polarities, namely a series of non-ionic, non-ionic comb-like, anionic and cationic hydrophilic blocks. The controlled character of the polymerizations was supported by the linear increase of the molar masses with conversion, monomodal molar mass distributions with low polydispersities and high degrees of end-group functionalization. The new macro-surfactants form micelles in water, whose size and geometry strongly depend on their composition, according to dynamic and static light scattering measurements. The micellization is shown to be thermodynamically favored, due to the high incompatibility of the blocks as indicated by thermal analysis of the block copolymers in bulk. The thermodynamic state in solution is found to be in the strong or super strong segregation limit. Nevertheless, due to the low glass transition temperature of the core-forming block, unimer exchange occurs between the micelles. Despite the dynamic character of the polymeric micellar systems, the aggregation behavior is strongly dependent on the history of the sample, i.e., on the preparation conditions. The aqueous micelles exhibit high stability upon temperature cycles, except for an irreversibly precipitating block copolymer containing a hydrophilic block exhibiting a lower critical solution temperature (LCST). Their exceptional stability upon dilution indicates very low critical micelle concentrations (CMC) (below 4∙10<sup>-4 g∙L<sup>-1). All non-ionic copolymers with sufficiently long solvophobic blocks aggregated into direct micelles in DMSO, too. Additionally, a new low-toxic highly hydrophilic sulfoxide block enables the formation of inverse micelles in organic solvents. The high potential of the new polymeric surfactants for many applications is demonstrated, in comparison to reference surfactants. The diblock copolymers are weakly surface-active, as indicated by the graduate decrease of the surface tension of their aqueous solutions with increasing concentration. No CMC could be detected. Their surface properties at the air/water interface confer anti-foaming properties. The macro-surfactants synthesized are surface-active at the interface between two liquid phases, too, since they are able to stabilize emulsions. The polymeric micelles are shown to exhibit a high ability to solubilize hydrophobic substances in water.
Aufgrund des großen Verhältnisses von Oberfläche zu Volumen zeigen Nanopartikel interessante, größenabhängige Eigenschaften, die man im ausgedehnten Festkörper nicht beobachtet. Sie sind daher von großem wissenschaftlichem und technologischem Interesse. Die Herstellung kleinster Partikel ist aus diesem Grund überaus wünschenswert. Dieses Ziel kann mit Hilfe von Mikroemulsionen als Templatphasen bei der Herstellung von Nanopartikeln erreicht werden. Mikroemulsionen sind thermodynamisch stabile, transparente und isotrope Mischungen von Wasser und Öl, die durch einen Emulgator stabilisiert sind. Sie können eine Vielzahl verschiedener Mikrostrukturen bilden. Die Kenntnis der einer Mikroemulsion zugrunde liegenden Struktur und Dynamik ist daher von außerordentlicher Bedeutung, um ein gewähltes System potentiell als Templatphase zur Nanopartikelherstellung einsetzen zu können. In der vorliegenden Arbeit wurden komplexe Mehrkomponentensysteme auf der Basis einer natürlich vorkommenden Sojabohnenlecithin-Mischung, eines gereinigten Lecithins und eines Sulfobetains als Emulgatoren mit Hilfe der diffusionsgewichteten 1H-NMR-Spektroskopie unter Verwendung gepulster Feldgradienten (PFG) in Abhängigkeit des Zusatzes des Polykations Poly-(diallyl-dimethyl-ammoniumchlorid) (PDADMAC) untersucht. Der zentrale Gegenstand dieser Untersuchungen war die strukturelle und dynamische Charakterisierung der verwendeten Mikroemulsionen hinsichtlich ihrer potentiellen Anwendbarkeit als Templatphasen für die Herstellung möglichst kleiner Nanopartikel. Die konzentrations- und zeit-abhängige NMR-Diffusionsmessung stellte sich dabei als hervorragend geeignete und genaue Methode zur Untersuchung der Mikrostruktur und Dynamik in den vorliegenden Systemen heraus. Die beobachtete geschlossene Wasser-in-Öl- (W/O-) Mikrostruktur der Mikroemulsionen zeigt deutlich deren potentielle Anwendbarkeit in der Nanopartikelsynthese. Das Gesamtdiffusionsverhalten des Tensides wird durch variierende Anteile aus der Verschiebung gesamter Aggregate, der Monomerdiffusion im Medium bzw. der medium-vermittelten Oberflächendiffusion bestimmt. Dies resultierte in einigen Fällen in einer anormalen Diffusionscharakteristik. In allen Systemen liegen hydrodynamische und direkte Wechselwirkungen zwischen den Tensidaggregaten vor. Der Zusatz von PDADMAC zu den Mikroemulsionen resultiert in einer Stabilisierung der flüssigen Grenzfläche der Tensidaggregate aufgrund der Adsorption des Polykations auf den entgegengesetzt geladenen Tensidfilm und kann potentiell zu Nanopartikeln mit kleineren Dimensionen und schmaleren Größenverteilungen führen.
Polymere sind zweifelsohne der Werkstoff in unserer Zeit. Ein bedeutender Anteil der heute industriell produzierten Polymere wird durch Emulsionspolymerisation hergestellt. Obwohl die Emulsionspolymerisation breite Anwendung findet, sind die involvierten Mechanismen von Teilchenbildung und -wachstum noch heute Gegenstand heftiger Kontroversen. Ein Spezialfall der Emulsionspolymerisation ist die emulgatorfreie Emulsionspolymerisation. Hierbei handelt es sich um ein scheinbar einfacheres System der Emulsionspolymerisation, weil diese Methode ohne Zusatz von Emulgatoren auskommt. Die Teilchenbildung ist ein fundamentaler Vorgang im Verlauf der Emulsionspolymerisation, da sie zur Ausbildung der polymeren Latexphase führt. Detaillierte Kenntnisse zum Mechanismus der Nukleierung ermöglichen eine bessere Kontrolle des Reaktionsverlaufes und damit der Eigenschaften des Endproduktes der Emulsionspolymerisation, dem Polymer-Latex. Wie bereits vorangegangene Arbeiten auf dem Gebiet der emulgatorfreien Emulsionspolymerisation von Styrol sowie Methylmethacrylat und Vinylacetat zeigen konnten, verläuft die Teilchenbildung in diesen Systemen über den Mechanismus der aggregativen Nukleierung. Im Zusammenhang mit den Ergebnissen der genannten Arbeiten tauchte dabei immer wieder ein interessanter Effekt im Bereich der Partikelnukleierung auf. Dieses als JUMBO-Effekt bezeichnete Phänomen zeigte sich reproduzierbar in einem Anstieg der Transmission im Bereich der Teilchenbildung von emulgatorfreien Emulsionspolymerisationen von Styrol, MMA und VAc. Nach der Initiierung der Polymerisation in einer wässrigen Monomerlösung durch Kaliumperoxodisulfat steigt die Durchlässigkeit bei 546 nm auf über 100 % an. Für diese „Abnahme der optischen Dichte“ wurden verschiedene Erklärungsmöglichkeiten vorgeschlagen, jedoch blieb ein Nachweis der Ursache für den JUMBO-Effekt bisher aus. Dieser Mangel an Aufklärung eines offenbar grundlegenden Phänomens in der emulgatorfreien Emulsionspolymerisation bildet den „Nukleus“ für die vorlie¬gende Arbeit. Durch die vorliegende Dissertation konnte das Verständnis für Phänomene der Teilchenbildung in der emulgatorfreien Emulsionspolymerisation von Styrol mit KPS erweitert werden. In diesem Rahmen wurde das Online-Monitoring des Polymerisationsvorganges verbessert und um verschiedene Methoden erweitert: Zur simultanen Erfassung von Trübungsdaten bei verschiedenen Wellenlängen konnte ein modernes Spektrometer in Kombination mit einer Lichtleitersonde in die Reaktionsapparatur integriert werden. Es wurde ein verbesserter Algorithmus zur Datenbearbeitung für die Partikelgrößenbestimmung mittels faseroptischer dynamischer Lichtstreuung entwickelt. Es wurden Online-Partikelgrößenanalysen mittels statischer Vielwinkellichtstreuung bei Polymerisationen direkt in entsprechenden Lichtstreuküvetten durchgeführt. Diese zur Beschreibung des untersuchten Systems eingeführten Methoden sowie ein zeitlich vollständiges Monitoring des gesamten Polymerisationsverlaufes, beginnend mit der Zugabe von Monomer zu Wasser, führten zu neuen Erkenntnissen zur emulgatorfreien Emulsionspolymerisation. Es wurden große Monomeraggregate, die sog. Nanotröpfchen, in wässriger Lösung (emulgatorfrei) nachgewiesen. Diese Aggregate bilden sich spontan und treten verstärkt in entgastem Wasser auf. Die Existenz von Nanotröpfchen in Verbindung mit Trübungs- und gaschromatografischen Messungen lässt auf eine molekular gelöste „Wirkkonzentration“ von Styrol in Wasser schließen, die bedeutend geringer ist als die absolute Sättigungskonzentration. Es konnten Hinweise auf eine Reaktion höherer Ordnung im System Wasser/Styrol/KPS gefunden werden. Es konnte gezeigt werden, dass eine präzise Einstellung der Nukleierungsdauer über die Zeit der Equilibrierung von Wasser mit Styrol möglich ist. Der JUMBO-Effekt, dem in dieser Arbeit ein besonderes Interesse galt, konnte in gewisser Weise entmystifiziert werden. Es konnte gezeigt werden, dass die Durchlässigkeit der Reaktionsmischung bereits beim Lösen von Styrol in Wasser durch Bildung von Styrolaggregaten abnimmt. Der darauf folgende kurzzeitige Transmissionsanstieg im Zusammenhang mit der Nukleierung erreicht dabei nicht mehr 100 % des Referenzwertes von reinem Wasser. Alle experimentellen Daten sprechen für die Nanotröpfchen als Ursache des JUMBO-Effekts. Wie die Ergebnisse dieser Arbeit zeigen, ist selbst das relativ „einfache“ System der emulgatorfreien Emulsionspolymerisation komplizierter als angenommen. Die Existenz von großen Styrolaggregaten in wässriger Lösung erfordert eine neue Betrachtungsweise des Reaktionssystems, in die auch der Lösungszustand des Monomers mit einbezogen werden muss.
Immobilisierung bzw. Mobilisierung und Transport von Schadstoffen in der Umwelt, besonders in den Kompartimenten Boden und Wasser, sind von fundamentaler Bedeutung für unser (Über)Leben auf der Erde. Einer der Hauptreaktionspartner für organische und anorganische Schadstoffe (Xenobiotika) in der Umwelt sind Huminstoffe (HS). HS sind Abbauprodukte pflanzlichen und tierischen Gewebes, die durch eine Kombination von chemischen und biologischen Ab- und Umbauprozessen entstehen. Bedingt durch ihre Genese stellen HS außerordentlich heterogene Stoffsysteme dar, die eine Palette von verschiedenartigen Wechselwirkungen mit Schadstoffen zeigen. Die Untersuchung der fundamentalen Wechselwirkungsmechanismen stellt ebenso wie deren quantitative Beschreibung höchste Anforderungen an die Untersuchungsmethoden. Zur qualitativen und quantitativen Charakterisierung der Wechselwirkungen zwischen HS und Xenobiotika werden demnach analytische Methoden benötigt, die bei der Untersuchung von extrem heterogenen Systemen aussagekräftige Daten zu liefern vermögen. Besonders spektroskopische Verfahren, wie z.B. lumineszenz-basierte Verfahren, besitzen neben der hervorragenden Selektivität und Sensitivität, auch eine Multidimensionalität (bei der Lumineszenz sind es die Beobachtungsgrößen Intensität IF, Anregungswellenlänge lex, Emissionswellenlänge lem und Fluoreszenzabklingzeit tF), die es gestattet, auch heterogene Systeme wie HS direkt zu untersuchen. Zur Charakterisierung können sowohl die intrinsischen Fluoreszenzeigenschaften der HS als auch die von speziell eingeführten Lumineszenzsonden verwendet werden. In beiden Fällen werden die zu Grunde liegenden fundamentalen Konzepte der Wechselwirkungen von HS mit Xenobiotika untersucht und charakterisiert. Für die intrinsische Fluoreszenz der HS konnte gezeigt werden, dass neben molekularen Strukturen besonders die Verknüpfung der Fluorophore im Gesamt-HS-Molekül von Bedeutung ist. Konformative Freiheit und die Nachbarschaft zu als Energieakzeptor fungierenden HS-eigenen Gruppen sind wichtige Komponenten für die Charakteristik der HS-Fluoreszenz. Die Löschung der intrinsischen Fluoreszenz durch Metallkomplexierung ist demnach auch das Resultat der veränderten konformativen Freiheit der HS durch die gebundenen Metallionen. Es zeigte sich, dass abhängig vom Metallion sowohl Löschung als auch Verstärkung der intrinsischen HS-Fluoreszenz beobachtet werden kann. Als extrinsische Lumineszenzsonden mit wohl-charakterisierten photophysikalischen Eigenschaften wurden polyzyklische aromatische Kohlenwasserstoffe und Lanthanoid-Ionen eingesetzt. Durch Untersuchungen bei sehr niedrigen Temperaturen (10 K) konnte erstmals die Mikroumgebung von an HS gebundenen hydrophoben Xenobiotika untersucht werden. Im Vergleich mit Raumtemperaturexperimenten konnte gezeigt werden, dass hydrophobe Xenobiotika an HS-gebunden in einer Mikroumgebung, die in ihrer Polarität analog zu kurzkettigen Alkoholen ist, vorliegen. Für den Fall der Metallkomplexierung wurden Energietransferprozesse zwischen HS und Lanthanoidionen bzw. zwischen verschiedenen, gebundenen Lanthanoidionen untersucht. Basierend auf diesen Messungen können Aussagen über die beteiligten elektronischen Zustände der HS einerseits und Entfernungen von Metallbindungsstellen in HS selbst angeben werden. Es ist dabei zu beachten, dass die Experimente in Lösung bei realen Konzentrationen durchgeführt wurden. Aus Messung der Energietransferraten können direkte Aussagen über Konformationsänderungen bzw. Aggregationsprozesse von HS abgeleitet werden.
Understanding the principles of self-organisation exhibited by block copolymers requires the combination of synthetic and physicochemical knowledge. The ability to synthesise block copolymers with desired architecture facilitates the ability to manipulate their aggregation behaviour, thus providing the key to nanotechnology. Apart from relative block volumes, the size and morphology of the produced nanostructures is controlled by the effective incompatibility between the different blocks. Since polymerisation techniques allowing for the synthesis of well-defined block copolymers are restricted to a limited number of monomers, the ability to tune the incompatibility is very limited. Nevertheless, Polymer Analogue Reactions can offer another possibility for the production of functional block copolymers by chemical modifications of well-defined polymer precursors. Therefore, by applying appropriate modification methods both volume fractions and incompatibility, can be adjusted. Moreover, copolymers with introduced functional units allow utilization of the concept of molecular recognition in the world of synthetic polymers. The present work describes a modular synthetic approach towards functional block copolymers. Radical addition of functional mercaptanes was employed for the introduction of diverse functional groups to polybutadiene-containing block copolymers. Various modifications of 1,2-polybutadiene-poly(ethylene oxide) block copolymer precursors are described in detail. Furthermore, extension of the concept to 1,2-polybutadiene-polystyrene block copolymers is demonstrated. Further investigations involved the self-organisation of the modified block copolymers. Formed aggregates in aqueous solutions of block copolymers with introduced carboxylic acid, amine and hydroxyl groups as well as fluorinated chains were characterised. Study of the aggregation behaviour allowed general conclusions to be drawn regarding the influence of the introduced groups on the self-organisation of the modified copolymers. Finally, possibilities for the formation of complexes, based on electrostatic or hydrogen-bonding interactions in mixtures of block copolymers bearing mutually interacting functional groups, were investigated.
In this work, the nonaqueous synthesis of binary and ternary metal oxide nanoparticles is investigated for a number of technologically important materials. A strong focus was put on studying the reaction mechanisms leading to particle formation upon solvothermal treatment of the precursors, as an understanding of the formation processes is expected to be crucial for a better control of the systems, offering the potential to tailor particle size and morphology. The synthesis of BaTiO3 was achieved by solvothermal reaction of metallic barium and titanium isopropoxide in organic solvents. Phase-pure, highly crystalline particles about 6 nm in size resulted in benzyl alcohol, whereas larger particles could be obtained in ketones such as acetone or acetophenone. In benzyl alcohol, a novel mechanism was found to lead to BaTiO3, involving a C–C coupling step between the isopropoxide ligand and the benzylic carbon of the solvent. The resulting coupling product, 4-phenyl-2-butanol, is found in almost stoichiometric yield. The particle formation in ketones proceeds via a Ti-mediated aldol condensation of the solvent, involving formal elimination of water which induces formation of the oxide. These processes also occurred when reacting solely the titanium alkoxide with ketones or aldehydes, leading to highly crystalline anatase nanoparticles for all tested solvents. In ketones, also the synthesis of nanopowders of lead zirconate titanate (PZT) was achieved, which were initially amorphous but could be crystallized by calcination at moderate temperatures. Additionally, PZT films were prepared by simply casting a suspension of the powder onto Si substrates followed by calcination.Solvothermal synthesis however is not restricted to alkoxides as precursors but is also achieved from metal acetylacetonates. The use of benzylamine as solvent proved particularly versatile, making possible the synthesis of nanocrystalline In2O3, Ga2O3, ZnO and iron oxide from the respective acetylacetonates. During the synthesis, the acetylacetonate ligand undergoes a solvolysis under C–C cleavage, resulting in metal-bound enolate ligands which, in analogy to the synthesis in ketones, induce ketimine and aldol condensation reactions. In the last section of this work, surface functionalization of anatase nanoparticles is explored. The particles were first capped with various organic ligands via a facile in situ route, which resulted in altered properties such as enhanced dispersibility in various solvents. In a second step, short functional oligopeptide segments were attached to the particles by means of a catechol linker to achieve advanced self-assembly properties.
Reversible addition-fragmentation transfer (RAFT) was used as a controlling technique for studying the aqueous heterophase polymerization. The polymerization rates obtained by calorimetric investigation of ab initio emulsion polymerization of styrene revealed the strong influence of the type and combination of the RAFT agent and initiator on the polymerization rate and its profile. The studies in all-glass reactors on the evolution of the characteristic data such as average molecular weight, molecular weight distribution, and average particle size during the polymerization revealed the importance of the peculiarities of the heterophase system such as compartmentalization, swelling, and phase transfer. These results illustrated the important role of the water solubility of the initiator in determining the main loci of polymerization and the crucial role of the hydrophobicity of the RAFT agent for efficient transportation to the polymer particles. For an optimum control during ab-initio batch heterophase polymerization of styrene with RAFT, the RAFT agent must have certain hydrophilicity and the initiator must be water soluble in order to minimize reactions in the monomer phase. An analytical method was developed for the quantitative measurements of the sorption of the RAFT agents to the polymer particles based on the absorption of the visible light by the RAFT agent. Polymer nanoparticles, temperature, and stirring were employed to simulate the conditions of a typical aqueous heterophase polymerization system. The results confirmed the role of the hydrophilicity of the RAFT agent on the effectiveness of the control due to its fast transportation to the polymer particles during the initial period of polymerization after particle nucleation. As the presence of the polymer particles were essential for the transportation of the RAFT agents into the polymer dispersion, it was concluded that in an ab initio emulsion polymerization the transport of the hydrophobic RAFT agent only takes place after the nucleation and formation of the polymer particles. While the polymerization proceeds and the particles grow the rate of the transportation of the RAFT agent increases with conversion until the free monomer phase disappears. The degradation of the RAFT agent by addition of KPS initiator revealed unambigueous evidence on the mechanism of entry in heterophase polymerization. These results showed that even extremely hydrophilic primary radicals, such as sulfate ion radical stemming from the KPS initiator, can enter the polymer particles without necessarily having propagated and reached a certain chain length. Moreover, these results recommend the employment of azo-initiators instead of persulfates for the application in seeded heterophase polymerization with RAFT agents. The significant slower rate of transportation of the RAFT agent to the polymer particles when its solvent (styrene) was replaced with a more hydrophilic monomer (methyl methacrylate) lead to the conclusion that a complicated cooperative and competitive interplay of solubility parameters and interaction parameter with the particles exist, determining an effective transportation of the organic molecules to the polymer particles through the aqueous phase. The choice of proper solutions of even the most hydrophobic organic molecules can provide the opportunity of their sorption into the polymer particles. Examples to support this idea were given by loading the extremely stiff fluorescent molecule, pentacene, and very hydrophobic dye, Sudan IV, into the polymer particles. Finally, the first application of RAFT at room temperature heterophase polymerization is reported. The results show that the RAFT process is effective at ambient temperature; however, the rate of fragmentation is significantly slower. The elevation of the reaction temperature in the presence of the RAFT agent resulted in faster polymerization and higher molar mass, suggesting that the fragmentation rate coefficient and its dependence on the temperature is responsible for the observed retardation.
Mesoporous organosilica materials with amine functions : surface characteristics and chirality
(2005)
In this work mesoporous organisilica materials are synthesized through the silica sol-gel process. For this a new class of precursors which are also surfactant are synthesized and self-assembled. This leads to a high surface area functionality which is analysized with copper (II) and water adsorption.
Ziel dieser Arbeit war die Entwicklung neuer Substanzen für die Gentherapie. Diese beinhaltet die Behebung von erblich bedingten Krankheiten wie z.B. Mucoviscidose. Dabei werden im Zellkern defekte Gene durch normale, gesunde DNA-Sequenzen ersetzt. Zur Einschleusung des Genmaterials in die Zellen (Transfektion) werden geeignete Transport-Systeme bzw. Methoden benötigt, die dort die Freisetzung der neu einzubauenden Gene (Genexpression ausgedrückt in Transfektionseffizienzen) gestatten. Hierfür wurden neue Polykation-DNA-Komplexe (Vektoren) auf Basis kationischer Polymere wie Poly(ethylenimin) (PEI) hergestellt, charakterisiert und nachfolgend in Transfektionsversuchen an verschiedenen Zelllinien eingesetzt. Sowohl das kationische Ausgangspolymer PEI als auch das Pfropfcopolymer PEI-g-PEO (PEO-Seitenketten zur Erhöhung der Biokompatibilität) wurden mit Rezeptorliganden modifiziert, um eine verbesserte und spezifische Transfektion an ausgesuchten Zellen zu erreichen. Als Liganden wurden Folsäure (Transfektion an HeLa-Zellen), Triiod-L-thyronin (HepG2-Zellen) und die Uronsäuren der Galactose, Mannose, Glucose sowie die Lactobionsäure (HeLa-, HepG2- und 16HBE-Zellen) verwendet. Das PEI, die Pfropfcopolymere PEI-g-PEO und die Ligand-funktionalisierten Copolymere wurden hinsichtlich ihrer chemischen Zusammensetzung und molekularen Parameter charakterisiert. Die Molmassenuntersuchungen mittels Größenausschlusschromatographie zeigten, dass nach der Synthese unterschiedliche Polymerfraktionen mit nicht einheitlicher chemischer Zusammensetzung vorlagen. Die anschließenden Transfektionsversuche wurden mit Hilfe einer speziellen DNA (Luciferase) an den Zelllinien HepG2 (Leberkrebszellen), HeLa (Gebärmutterhalskrebszellen) und 16HBE (Atemwegsepithelzellen) durchgeführt. Die T3(Triiod-L-thyronin)-Vektoren zeigten in Abhängigkeit vom eingesetzten Komplexverhältnis Polykation/DNA ein Maximum in der Transfektion an HepG2-Zellen. Die Hypothese der rezeptorvermittelten Endozytose ließ sich durch entsprechende T3-Überschuss-Experimente und Fluoreszenzmikroskopie-Untersuchungen bestätigen. Dagegen konnte bei den Folsäure-Vektoren keine rezeptorvermittelte Endozytose beobachtet werden. Bei den Vektoren mit Mannuronsäure-Ligand (Man) konnte an allen drei Zelllinien (HepG2, HeLa, 16HBE) eine konstante, hohe Transfereffizienz nachgewiesen werden. Sie waren bei allen eingesetzten Polymer-DNA-Verhältnissen effizienter als der Vergleichsvektor PEI. Dieses Transfektionsverhalten ließ sich durch Blockierung der Zuckerstruktur unterbinden. In Transfektionsexperimenten mit einem Überschuss an freier Mannuronsäure und fluoreszenzmikroskopischen Untersuchungen konnte eine rezeptorvermittelte Endozytose der Man-Vektoren an den o.g. Zelllinien nachgewiesen werden. Die anderen Uronsäure-Konjugate zeigten keine signifikanten Abweichungen im Transfektionsverhalten im Vergleich zum PEI-Vektor.
In dieser Arbeit wird ein chemisches Abgussverfahren für selbstorganisierte Strukturen in Lösung verwendet, das es ermöglicht definierte poröse Materialien mit Strukturierung auf der Nanometerskala herzustellen. Ähnlich wie beim Gussverfahren von Werkstücken wird die Vorlage durch ein geeignetes Material abgebildet. Durch Entfernen dieser Vorlage erhält man ein poröses (mit Hohlräumen durchsetztes) Negativ derselben. Die auf diese Weise erhaltenen Materialien sind in mehrerer Hinsicht interessant: So lassen sich aus ihrer Morphologie Rückschlüsse über die Natur der selbstorganisierten Strukturen erhalten, da der hier verwendete Abbildungsprozess selbst kleinste strukturelle Details erfasst. Die Hohlräume der synthetisierten porösen Stoffe hingegen können als winzige Reaktionsgefäße, sogenannte "Nano-Reaktoren" verwendet werden. Dies ermöglicht sowohl die Synthese von Nano-Partikeln, die auf anderem Wege nicht zugänglich sind, als auch die Möglichkeit Einflüsse der räumlichen Restriktion auf die Reaktion zu untersuchen. Besonders räumlich ausgedehnte Strukturen sollten hierbei Auffälligkeiten zeigen. Somit ist die Gliederung der Arbeit vorgegeben: - Die Herstellung und Charakterisierung von porösen Stoffen und selbstorganisierten Strukturen - Ihre Verwendung als "Nano-Reaktor"
Neue Einflüsse und Anwendungen von Mikrowellenstrahlung auf Miniemulsionen und ihre Kompositpolymere
(2004)
Miniemulsionen bestehen aus zwei miteinander nicht mischbaren Flüssigkeiten, von der die eine in Form kleiner Tröpfchen fein in der anderen verteilt (dispergiert) ist. Miniemulsionströpfchen sind mit Durchmessern von ungefähr 0,1 Mikrometer kleiner als herkömmliche Emulsionen und können u. a. als voneinander unabhängige Nanoreaktoren für chemische Reaktionen verwendet werden. Man unterteilt sie in direkte Miniemulsionen, in denen ein Öl in Wasser dispergiert ist, und inverse Miniemulsionen, in denen Wasser in Öl dispergiert wird. In dieser Arbeit wird das besondere chemische und physikalische Verhalten solcher Miniemulsionen unter dem Einfluß von Mikrowellenstrahlung untersucht. Dabei werden sowohl für Öl-in-Wasser als auch für Wasser-in-Öl-Miniemulsionen grundlagenwissenschaftliche Entdeckungen beschrieben und durch neue Modelle erklärt. Der praktische Nutzen dieser bislang unbeschriebenen Effekte wird durch ingenieurwissenschaftliche Anwendungsbeispiele im Bereich der Polymerchemie verdeutlicht. 1. Polymerisation mit "überlebenden Radikalen" (Surviving Radical Polymerization) Für die Herstellung von sog. Polymerlatizes (Kunststoffdispersionen, wie sie u. a. für Farben verwendet werden) aus direkten Styrol-in-Wasser Miniemulsionen werden die Styroltröpfchen als Nanoreaktoren verwendet: Sie werden mit Hilfe von Radikalen durch eine Kettenreaktion zu winzigen Polymerpartikeln umgesetzt, die im Wasser dispergiert sind. Ihre Materialeigenschaften hängen stark von der Kettenlänge der Polymermoleküle ab. In dieser Arbeit konnten durch den Einsatz von Mikrowellenstrahlung erstmals große Mengen an Radikalen erzeugt werden, die jeweils einzeln in Tröpfchen (Nanoreaktoren) auch noch lange Zeit nach dem Verlassen der Mikrowelle überleben und eine Polymerisationskettenreaktion ausführen können. Diese Methode ermöglicht nicht nur die Herstellung von Polymeren in technisch zuvor unerreichbaren Kettenlängen, mit ihr sind auch enorm hohe Umsätze nach sehr kurzen Verweilzeiten in der Mikrowelle möglich – denn die eigentliche Reaktion findet außerhalb statt. Es konnte gezeigt werden, dass durch Einsatz von Zusatzstoffen bei unvermindert hohem Umsatz die Polymerkettenlänge variiert werden kann. Die technischen Vorzüge dieses Verfahrens konnten in einer kontinuierlich betriebenen Pilotanlage nachgewiesen werden. 2. Aufheizverhalten inverser Miniemulsionen in Mikrowellenöfen Das Aufheizverhalen von Wasser-in-Öl Miniemulsionen mit kleinen Durchmessern durch Mikrowellen ist überaus träge, da sich nur das wenige Wasser in den Tröpfchen mit Mikrowellen aufheizen lässt, das Öl jedoch kaum. Solche Systeme verhalten sich gemäß der "Theorie des effektiven Mediums". Werden aber etwas größere Tröpfchen im Mikrometerbereich Mikrowellen ausgesetzt, so konnte eine wesentlich schnellere Aufheizung beobachtet werden, die auf eine Maxwell-Wagner-Grenzflächenpolarisation zurückgeführt werden kann. Die Größenabhängigkeit dieses Effekts wurde mit Hilfe der dielektrischen Spektroskopie quantifiziert und ist bislang in der Literatur nie beschrieben worden. Zur genauen Messung dieses Effekts und zu seiner technischen Nutzung wurde ein neuartiges Membranverfahren für die Herstellung von großen Miniemulsionströpfchen im Mikrometerbereich entwickelt. 3. Herstellung von Kompositpolymeren für Mikrowellenanwendungen Um die untersuchte Maxwell-Wagner-Grenzflächenpolarisation technisch nutzen zu können, wurden als dafür geeignete Materialien Kompositpolymere hergestellt. Das sind Kunststoffe, in denen winzige Wassertropfen oder Keramikpartikel eingeschlossen sind. Dazu wurden neuartige Synthesewege auf der Grundlage der Miniemulsionstechnik entwickelt. Ihr gemeinsames Ziel ist die Einschränkung der üblicherweise bei Polymerisation auftretenden Entmischung: In einem Verfahren wurde durch Gelierung die Beweglichkeit der emulgierten Wassertröpfchen eingeschränkt, in einem anderen wurde durch das Einschließen von Keramikpartikeln in Miniemulsionströpfchen die Entmischung auf deren Größe beschränkt. Anwendungen solcher Kompositpolymere könnten künstliche Muskeln, die Absorption von Radarstrahlung, z. B. für Tarnkappenflugzeuge, oder kratzfeste Lacke sein.Bei diesen Experimenten wurde beobachtet, daß sich u. U. in der Miniemulsion große Tröpfchen bilden. Ihr Ursprung wird mit einer neuen Modellvorstellung erklärt, die die Einflüsse auf die Stabilität von Miniemulsionen beschreibt.
New chain transfer agents based on dithiobenzoate and trithiocarbonate for free radical polymerization via Reversible Addition-Fragmentation chain Transfer (RAFT) were synthesized. The new compounds bear permanently hydrophilic sulfonate moieties which provide solubility in water independent of the pH. One of them bears a fluorophore, enabling unsymmetrical double end group labelling as well as the preparation of fluorescent labeled polymers. Their stability against hydrolysis in water was studied, and compared with the most frequently employed water-soluble RAFT agent 4-cyano-4-thiobenzoylsulfanylpentanoic acid dithiobenzoate, using UV-Vis and 1H-NMR spectroscopy. An improved resistance to hydrolysis was found for the new RAFT agents, providing good stabilities in the pH range between 1 and 8, and up to temperatures of 70°C. Subsequently, a series of non-ionic, anionic and cationic water-soluble monomers were polymerized via RAFT in water. In these experiments, polymerizations were conducted either at 48°C or 55°C, that are lower than the conventionally employed temperatures (>60°C) for RAFT in organic solvents, in order to minimize hydrolysis of the active chain ends (e.g. dithioester and trithiocarbonate), and thus to obtain good control over the polymerization. Under these conditions, controlled polymerization in aqueous solution was possible with styrenic, acrylic and methacrylic monomers: molar masses increase with conversion, polydispersities are low, and the degree of end group functionalization is high. But polymerizations of methacrylamides were slow at temperatures below 60°C, and showed only moderate control. The RAFT process in water was also proved to be a powerful method to synthesize di- and triblock copolymers including the preparation of functional polymers with complex structure, such as amphiphilic and stimuli-sensitive block copolymers. These include polymers containing one or even two stimuli-sensitive hydrophilic blocks. The hydrophilic character of a single or of several blocks was switched by changing the pH, the temperature or the salt content, to demonstrate the variability of the molecular designs suited for stimuli-sensitive polymeric amphiphiles, and to exemplify the concept of multiple-sensitive systems. Furthermore, stable colloidal block ionomer complexes were prepared by mixing anionic surfactants in aqueous media with a double hydrophilic block copolymer synthesized via RAFT in water. The block copolymer is composed of a noncharged hydrophilic block based on polyethyleneglycol and a cationic block. The complexes prepared with perfluoro decanoate were found so stable that they even withstand dialysis; notably they do not denaturate proteins. So, they are potentially useful for biomedical applications in vivo.
Taking inspiration from nature, where composite materials made of a polymer matrix and inorganic fillers are often found, e.g. bone, shell of crustaceans, shell of eggs, etc., the feasibility on making composite materials containing chitosan and nanosized hydroxyapatite were investigated. A new preparation approach based on a co-precipitation method has been developed. In its earlier stage of formation, the composite occurs as hydrogel as suspended in aqueous alkaline solution. In order to get solid composites various drying procedures including freeze-drying technique, air-drying at room temperature and at moderate temperatures, between 50oC and 100oC were used. Physicochemical studies showed that the composites exhibit different properties with respect to their structure and composition. IR and Raman spectroscopy probed the presence of both chitosan and hydroxyapatite in the composites. Hydroxyapatite as dispersed in the chitosan matrix was found to be in the nanosize range (15-50 nm) and occurs in a bimodal distribution with respect to its crystallite length. Two types of distribution domains of hydroxyapatite crystallites in the composite matrix such as cluster-like (200-400 nm) and scattered-like domains were identified by the transmission electron microscopy (TEM), X-ray diffraction (XRD) and by confocal scanning laser microscopy (CSLM) measurements. Relaxation NMR experiments on composite hydrogels showed the presence of two types of water sites in their gel networks, such as free and bound water. Mechanical tests showed that the mechanical properties of composites are one order of magnitude less than those of compact bone but comparable to those of porous bone. The enzymatic degradation rates of composites showed slow degradation processes. The yields of degradation were estimated to be less than 10% by loss of mass, after incubation with lysozyme, for a period of 50 days. Since the composite materials were found biocompatible by the in vivo tests, the simple mode of their fabrication and their properties recommend them as potential candidates for the non-load bearing bone substitute materials.
Gegenstand der Arbeit ist die lichtinduzierte Orientierung von multifunktionalen Polymeren, die u.a. für die Herstellung von optischen Schichten in Flüssigkristalldisplays verwendet werden können. Dafür wurden Polymere entwickelt, die wenigstens eine mesogene und eine lichtsensitive Gruppe enthalten. Diese Gruppen zeigen Eigenschaften, die für die Orientierung der kompletten Polymerfilme verantwortlich sind. Das Material wird dafür zunächst in einem ersten Schritt kurz mit linear polarisiertem Licht bestrahlt, wobei richtungsabhängig eine photochemische Reaktion an der lichtsensitiven Gruppe erfolgt und dadurch ein "Orientierungskeim" gelegt wird. Durch die thermische Ausrichtung der mesogenen Gruppen an den photochemisch generierten "Orientierungskeimen" erfolgt die komplette Orientierung des Filmes in einem zweiten Schritt. Dadurch wird eine hohe optische Anisotropie erhalten. Dieses Verfahren wurde als Zwei-Stufen-Bulk-Orientierungsprozess bezeichnet. In der vorliegenden Arbeit wurden die Photoreaktionen verschiedener lichtsensitiver Gruppen, wie z. B. Azobenzen, Stilben und Zimtsäureester und deren Orientierungsfähigkeit in flüssigkristallinen Polymeren untersucht. Der Orientierungsprozess wurde durch die Wahl geeigneter Bestrahlungsbedingungen optimiert. Die Effizienz der Orientierung wurde anhand der sich verändernden winkelabhängigen Absorptionseigenschaften und der Doppelbrechung des Materials analysiert. Es wurde gezeigt, dass eine effiziente lichtinduzierte Orientierung bei einer Vielzahl von flüssigkristallinen Polymeren realisierbar ist. So wurde z. B. erstmalig gefunden, dass durch eine Photo-Fries-Orientierung eine hohe optische Anisotropie erhalten werden kann. Außerdem wurde eine neue lichtsensitive Gruppe auf der Basis von Donor-Akzeptor-substituiertem Ethen entwickelt, die farbneutral ist und durch polarisiertes UV-Licht sowohl orientiert als auch re-orientiert werden kann. Es wurden weiterhin Polymere entwickelt, die zusätzlich zu den photosensitiven und flüssigkristallinen Einheiten, fluoreszierende Gruppen enthalten. Die Auswahl geeigneter Fluoreszenzverbindungen erfolgte aufgrund ihrer anisometrischen Form, ihrer Ordnungsparameter in einer niedermolekularen Flüssigkristallmischung und ihrer Photostabilität. Das Orientierungsverhalten von ausgewählten Fluorophoren wurde in sechs Ter- und zwei Copolymeren untersucht. Das Prinzip der Orientierung beruht auf einer kooperativen Ausrichtung der Seitengruppen. Aus diesem Grund kommt dem Nachweis der Kooperativität in der vorliegenden Arbeit eine besondere Stellung zu. Durch lichtinduzierte Bulk-Orientierung wurden Filme erhalten, welche durch eine richtungsabhängige Fluoreszenz und Absorption im sichtbaren- oder UV-Bereich charakterisiert sind. Die Fluoreszenz wird durch einige lichtsensitive Verbindungen komplett gelöscht. Die wahlweise erhaltenen anisotropen Filme von farbigen, fluoreszierenden oder farbneutralen Verbindungen, die zudem in kleinen Pixeln von wenigen Mikrometern orientiert werden können, eröffnen vielfältige Möglichkeiten für den Einsatz von multi-funktionalen Polymeren als optische Schichten in Flüssigkristalldisplays.
In this work, the basic principles of self-organization of diblock copolymers having the in¬herent property of selective or specific non-covalent binding were examined. By the introduction of electrostatic, dipole–dipole, or hydrogen bonding interactions, it was hoped to add complexity to the self-assembled mesostructures and to extend the level of ordering from the nanometer to a larger length scale. This work may be seen in the framework of biomimetics, as it combines features of synthetic polymer and colloid chemistry with basic concepts of structure formation applying in supramolecular and biological systems. The copolymer systems under study were (i) block ionomers, (ii) block copolymers with acetoacetoxy chelating units, and (iii) polypeptide block copolymers.
The goal of this work was to study the binding of ions to polymers and lipid bilayer membranes in aqueous solutions. In the first part of this work, the influence of various inorganic salts and polyelectrolytes on the structure of water was studied using Isothermal Titration Calorimetry (ITC). The heat of dilution of the salts was used as a scale of water structure making and breaking of the ions. The heats of dilution could be attributed to the Hofmeister Series. Following this, the binding of Ca2+ to poly(sodium acrylate) (NaPAA) was studied. ITC and a Ca2+ Ion Selective Electrode were used to measure the reaction enthalpy and binding isotherm. Binding of Ca2+ ions to PAA, was found to be highly endothermic and therefore solely driven by entropy. We then compared the binding of ions to the one-dimensional PAA polymer chain to the binding to lipid vesicles with the same functional groups. As for the polymer, Ca2+ binding was found to be endothermic. Binding of calcium to the lipid bilayer was found to be weaker than to the polymer. In the context of these experiments, it was shown that Ca2+ not only binds to charged but also to zwitterionic lipid vesicles. Finally, we studied the interaction of two salts, KCl and NaCl, to a neutral polymer gel, PNIPAAM, and to the ionic polymer PAA. Combining calorimetry and a potassium selective electrode we observed that the ions interact with both polymers, whether containing charges or not.
Polymer optical fibers (POFs) are a rather new tool for high-speed data transfer by modulated light. They allow the transport of high amounts of data over distances up to about 100 m without be influenced by external electromagnetic fields. Due to organic chemical nature of POFs, they are sensitive to the climate of their environment and therefore the optical fiber properties are as well. Hence, the optical stability is a key issue for long-term applications of POFs. The causes for a loss of optical transmission due to climatic exposures (aging/degradation) are researched by means of chemical analytical tools such as chemiluminescence (CL) and Fourier transform infrared (FTIR) spectroscopy for five different (with respect to manufacturers) step-index multimode PMMA based POFs and for seven different climatic conditions. Three of the five POF samples are studied more in detail to realize the effects of individual parameters and for forecasting longterm optical stability by short-term exposure tests. At first, the unexposed POF components (core, cladding, and bare POF as combination of core and cladding) are characterized with respect to important physical and chemical properties. The glass transition temperature Tg, and the melting temperature Tm are in the region of 120 °C to 140 °C, the molecular weight (Mw) of cores is in the order of 105 g mol-1. POFs are found to have different chemical compositions of their claddings as could be detected by FTIR, but identical compositions of their cores. Two of the POFs are exposed as cables (core, cladding and jacket) for about 3300 hours to the climate 92 °C / 95 % relative humidity (RH) resulting in a different transmission decrease. Investigating the related unexposed and exposed bare POFs for degradation using CL, FTIR, thermogravimetry (TG), UV/visible transmittance and gel permeation chromatography (GPC) suggest that claddings of POFs are more affected than cores. Probably the observed loss of transmission is mainly due to increased light absorption and imperfections at the core-cladding boundary caused by a large degradation of claddings. Hence, it is highly possible that the optical transmission stability of POFs is governed mainly by the thermo-oxidative stability of the cladding and minor of the core. Three bare POFs (core and cladding only) are exposed for different duration of exposure time (30 hours to 4500 hours) to 92 °C / 95 %RH, 92 °C / 50 %RH, 50 °C / 95 %RH, 90 °C / low humidity, 100 °C / low humidity, 110 °C / low humidity and 120 °C / low humidity. In these climates their transmission variations are found to be different from each other, too. The outcomes strongly inform that under high temperature and high humid climates physical changes such as volume expansion, are the main sources for the loss of optical transmission. Also, the optical transmission stability of POFs is found to be dependent on chemical compositions of claddings. Under high temperature and low humid conditions, a loss of transmission at the early stages of the exposure is mainly caused by physical changes, presumable by corecladding interface imperfections. For the later stages of exposures it is proposed to an additional increase of light absorption by core and cladding owes to degradation. Optical simulation results obtained parallel by Mr. L. Jankowski (a PhD student of BAM) are found to confirm these results. For bare POFs, too, the optical stability of POFs seems to depend on their thermo-oxidative stability. Some short-term exposure tests are conducted to realize influences of individual climatic parameters on the transmission property of POFs. It is found that at stationary high temperature and variable humidity conditions POFs display to a certain amount a reversible transmission loss due to physically absorbed water. But in the case of varying temperature and constant high humidity such reversibility is hardly noticeable. However, at room temperature and varying humidity, POFs display fully reversible transmission loss. The whole research described above has to be regarded as a starting point for further investigations. The restricted distribution of fundamental POF data by the manufacturers and the time consuming aging by climatic exposures restrict the results more or less to the samples, investigated here. Significant general statements require for example additional information concerning the variation of POF properties due to production. Nevertheless the tests, described here, have the capability for approximating and forecasting the long-term optical transmission stability of POFs. -------------- Auch im Druck erschienen: Appajaiah, Anilkumar: Climatic stability of polymer optical fibers (POF) / Anilkumar Appajaiah. - Bremerhaven : Wirtschaftsverl. NW, Verl. für neue Wiss., 2005. - Getr. Zählung [ca. 175 S.]. : Ill., graph. Darst. - (BAM-Dissertationsreihe ; 9) ISBN 3-86509-302-7
Die vorliegende Arbeit beschreibt das Verhalten von Polypeptid-Blockcopolymeren in der festen Phase und in selektiven Lösungsmitteln. Blockcopolymere auf Basis von Poly(L-glutaminsäure-5-benzylester) (PBLGlu) oder Poly(Nε-benzoyloxycarbonyl-L-lysin) (PZLLys), die in dieser Arbeit eingesetzt wurden, besitzen wegen ihrer helikalen Sekundärstruktur eine sog. Stäbchen-Knäuel-Geometrie, wobei die Knäuelkomponente Polystyrol oder Polybutadien ist. Die Phasenbildung dieser Blockcopolymere ist durch die Packungseigenschaften des rigiden Blocks beeinflusst. Es wurden bevorzugt lamellare Strukturen gebildet, in denen die Stäbchen parallel angeordnet sind. Das Vorhandensein eines permanenten Dipolmomentes führt zur Wechselwirkung zwischen den Helices und zur Erhöhung des Ordnungsgrades in der Phase. Ein zusätzlicher Parameter, der die Morphologie der Phase beeinflußt, ist die Chiralität der Peptidhelix, durch die chirale Überstrukturen induziert werden. In dünnen Filmen (40 nm), wo die Geometrie begrenzt ist, führt es zu Frustrationen in der Phase. Die dadurch entstandene Spannung wurde durch einen zick-zack-artigen Lamellenverlauf abgebaut. In selektiven Lösungsmitteln für die synthetische Komponente (PS) bilden die Polypeptid-Blockcopolymere vesikuläre Strukturen, deren kugel- oder wurmförmige Geometrie von der Elastizität der Membran abhängig ist. Durch Entfernung der Z-Schutzgruppe kann PZLLys in eine wasserlösliche Form überführt werden, so dass die PB-PLLys Blockcopolymere unter Bildung von Vesikeln in Wasser löslich sind. Dabei ist die Konformation des Peptids vom pH-Wert des Mediums abhängig und kann von einem Knäuel zu einer Helix reversibel geschaltet werden. Beim Modifizieren der Sekundärstruktur wurde eine Änderung der Aggregationszahl beobachtet. Somit können diese Blockcopolymere für die Herstellung von schaltbaren Aggregaten eingesetzt werden.
Ellipsometrische Lichtstreuung als neue Methode zur Charakterisierung der Grenzfläche von Kolloiden
(2004)
Die ellipsometrische Lichtstreuung wird als eine neue, leistungsfähige Methode zur Charakterisierung von Schichten um kolloidale Partikel vorgestellt. Theoretische Grundlage der Methode ist die Mie-Theorie der Lichtstreuung. Experimentell wurde die Polarisationsoptik eines Null-Ellipsometers in den Strahlengang eines Lichtstreuaufbaus eingebaut. Wie in der Reflexionsellipsometrie um den Brewsterwinkel herum erhält man in der ellipsometrischen Streuung einen Winkelbereich, in dem die Methode empfindlich auf Schichten an der Oberfläche der Partikel ist. An verschiedenen Systemen wurde die Tauglichkeit der ellipsometrischen Streuung zur Charakterisierung von Schichten auf Partikeln demonstriert. So wurden Dicke und Brechungsindex einer thermosensitiven Schicht von Poly(N-isopropylacrylamid) auf einem Poly(methylmethacrylat)-Kern bestimmt. Damit ist es möglich, experimentell den Schichtbrechungsindex und damit den Quellungsgrad zu bestimmen. Des Weiteren wurde der Einfluss der NaCl-Konzentration auf die Polyelektrolythülle von Poly(methylmethacrylat)-Poly(styrolsulfonat)-Blockcopolymer-Partikeln untersucht. Die Polyelektrolytketten liegen im hier untersuchten Beispiel nicht gestreckt vor. Als drittes wurde die Verteilung von niedermolekularen Ionen um elektrostatisch stabilisierte Poly(styrol)-Latexpartikel in Wasser untersucht. Hier wurde gezeigt, dass die beobachteten Schichtdicken und Schichtbrechungsindizes viel größer sind, als nach der klassischen Poisson-Boltzmann-Theorie zu erwarten ist. Des Weiteren wurde die Doppelbrechung von unilamellaren Lipidvesikeln bestimmt. Außerdem wurden Messungen der dynamische Lichtstreuung im Intensitätsminimum der Ellipsometrie durchgeführt. Dabei wird ein Prozess mit einer Korrelationszeit, die unabhängig vom Streuvektor, aber abhängig von der verwendeten Wellenlänge ist, sichtbar. Die Natur dieses Prozesses konnte hier nicht vollständig geklärt werden.
In dieser Arbeit wurden die Molekülstrukturen und die elektronischen Eigenschaften von Vanadium(IV)- und Oxo-Rhenium(V)-Chelaten mit einem kombinierten molekülmechanisch-quantenchemischen Ansatz untersucht, um sterische und elektronische Effekte der Komplexierung mit einem theoretischen Modell zu quantifizieren. Es konnte gezeigt werden, daß auf diese Weise detaillierte Aussagen zu den Bindungsverhältnissen der Metallchelate getroffen werden können. Die Berechnung der Molekülstrukturen gelingt mit exzellenter Übereinstimmung mit den Kristallstrukturen der Komplexe. Die molekülmechanischen Berechnungen erfolgen auf der Grundlage des Extensible Systematic Force Field ESFF und des Consistent Force Field 91 (CFF91). Dabei konnte die hohe Flexibilität und Zuverlässigkeit des regelbasierten ESFF für eine Vielzahl verschiedenster Metallchelate nachgewiesen werden. Aufgrund der mangelhaften Ergebnisse für trigonal-prismatische Komplexgeometrien mit dem ESFF wurden eine Anpassung des CFF91 für derartige Vanadiumkomplexe vorgenommen. Auf Grundlage von theoretischen Ergebnissen wurden die alternativen Strukturen von isoelektronischen Vanadiumkomplexen berechnet und in Übereinstimmung mit experimentellen Daten, theoretischen Modellen der Komplexchemie und empirischen Fakten eine Hypothese für die Ursache der strukturellen Differenzen erarbeitet. Der hier vorgestellte, kombinierte Algorithmus aus kraftfeldbasierter Geometrieoptimierung und single-point-Rechnung an diesen Strukturen ist ein zuverlässiger und relativ schneller Weg Molekülgeometrien von Metallkomplexen zu berechnen. Er kann somit zur Voraussagen von Komplexstrukturen und zur gezielten Modellierung definierter Koordinationsgeometrien verwendet werden.
Combining the magnetic properties of a given material with the tremendous advantages of colloids can exponentially increase the advantages of both systems. This thesis deals with the field of magnetic nanotechnology. Thus, the design and characterization of new magnetic colloids with fascinating properties compared with the bulk materials is presented. Ferrofluids are referred to either as water or organic stable dispersions of superparamagnetic nanoparticles which respond to the application of an external magnetic field but lose their magnetization in the absence of a magnetic field. In the first part of this thesis, a three-step synthesis for the fabrication of a novel water-based ferrofluid is presented. The encapsulation of high amounts of magnetite into polystyrene particles can efficiently be achieved by a new process including two miniemulsion processes. The ferrofluids consist of novel magnetite polystyrene nanoparticles dispersed in water which are obtained by three-step process including coprecipitation of magnetite, its hydrophobization and further surfactant coating to enable the redispersion in water and the posterior encapsulation into polystyrene by miniemulsion polymerization. It is a desire to take advantage of a potential thermodynamic control for the design of nanoparticles, and the concept of "nanoreactors" where the essential ingredients for the formation of the nanoparticles are already in the beginning. The formulation and application of polymer particles and hybrid particles composed of polymeric and magnetic material is of high interest for biomedical applications. Ferrofluids can for instance be used in medicine for cancer therapy and magnetic resonance imaging. Superparamagnetic or paramagnetic colloids containing iron or gadolinium are also used as magnetic resonance imaging contrast agent, for example as a important tool in the diagnosis of cancer, since they enhance the relaxation of the water of the neighbouring zones. New nanostructured composites by the thermal decomposition of iron pentacarbonyl in the monomer phase and thereafter the formation of paramagnetic nanocomposites by miniemulsion polymerization are discussed in the second part of this thesis. In order to obtain the confined paramagnetic nanocomposites a two-step process was used. In the first step, the thermal decomposition of the iron pentacarbonyl was obtained in the monomer phase using oleic acid as stabilizer. In the second step, this iron-containing monomer dispersion was used for making a miniemulsion polymerization thereof. The addition of lanthanide complexes to ester-containing monomers such as butyl acrylate and subsequent polymerization leading to the spontaneous formation of highly organized layered nanocomposites is presented in the final part of this thesis. By an one-step miniemulsion process, the formation of a lamellar structure within the polymer nanoparticles is achieved. The magnetization and the NMR relaxation measurements have shown these new layered nanocomposites to be very apt for application as contrast agent in magnetic resonance imaging.
During the past several decades polymer materials become widely used as components of medical devices and implants such as hemodialysers, bioartificial organs as well as vascular and recombinant surgery. Most of the devices cannot avoid the blood contact in their use. When the polymer materials come in contact with blood they can cause different undesired host responses like thrombosis, inflammatory reactions and infections. Thus the materials must be hemocompatible in order to minimize these undesired body responses. The earliest and one of the main problems in the use of blood-contacting biomaterials is the surface induced thrombosis. The sequence of the thrombus formation on the artificial surfaces has been well established. The first event, which occurs, after exposure of biomaterials to blood, is the adsorption of blood proteins. Surface physicochemical properties of the materials as wettability greatly influence the amount and conformational changes of adsorbed proteins. In turn the type, amount and conformational state of the adsorbed protein layer determines whether platelets will adhere and become activated or not on the artificial surface and thus to complete the thrombus formation. The adsorption of fibrinogen (FNG), which is present in plasma, has been shown to be closely related to surface induced thrombosis by participating in all processes of the thrombus formation such as fibrin formation, platelet adhesion and aggregation. Therefore study the FNG adsorption to artificial surfaces could contribute to better understanding of the mechanisms of platelet adhesion and activation and thus to controlling the surface induced thrombosis. Endothelization of the polymer surfaces is one of the strategies for improving the materials hemocompatibility, which is believed to be the most ideal solution for making truly blood-compatible materials. Since at physiological conditions proteins such as FNG and fibronectin (FN) are the usual extracellular matrix (ECM) for endothelial cells (EC) adhesion, precoating of the materials with these proteins has been shown to improve EC adhesion and growth in vitro. ECM proteins play an essential role not only like a structural support for cell adhesion and spreading, but also they are important factor in transmitting signals for different cell functions. The ability of cells to remodel plasma proteins such as FNG and FN in matrix-like structures together with the classical cell parameters such as actin cytoskeleton and focal adhesion formation could be used as an criteria for proper cell functioning. The establishment and the maintaining of delicate balance between cell-cell and cell-substrate contacts is another important factor for better EC colonization of the implants. The functionality of newly established endothelium in order to produce antithromotic substances should be always considered when EC seeding is used for improving the hemocompatibility of the polymer materials. Controlling the polymer surface properties such as surface wettability represents a versatile approach to manipulate the above cellular responses and therefore can be used in biomaterial and tissue engineering applications for producing better hemocompatible materials.
Ein Spezialgebiet der modernen Mikroelektronik ist die Miniaturisierung und Entwicklung von neuen nanostrukturierten und Komposit-Materialen aus 3d-Metallen. Durch geeignete Zusammensetzungen können diese sowohl mit einer hohen Sättigungsmagnetisierung und Koerzitivfeldstärke als mit besserer Oxidationsbeständigkeit im Vergleich zu den reinen Elementen erzielt werden. In der vorliegenden Arbeit werden neue Methoden für die Herstellung von bimetallischen kolloidalen Nanopartikeln vor allem mit einer Kern-Hülle-Struktur (Kern@Hülle) präsentiert. Bei der überwiegenden Zahl der vorgestellten Reaktionen handelt es sich um die thermische Zersetzung von metallorganischen Verbindungen wie Kobaltcarbonyl, Palladium- und Platinacetylacetonate oder die chemische Reduktion von Metallsalze mit langkettigem Alkohol in organischem Lösungsmittel. Daneben sind auch Kombinationen aus diesen beiden Verfahren beschrieben. Es wurden Kolloide aus einem reinen Edelmetall (Pt, Pd, Ag) in einem organischen Lösungsmittel synthetisiert und daraus neue, bisher in dieser Form nicht bekannte Ag@Co-, Pt@Co-, Pd@Co- und Pt@Pd@Co-Nanopartikel gewonnen. Der Kobaltgehalt der Ag@Co-, Teilchen konnte im Bereich von 5 bis 73 At. % beliebig eingestellt werden. Der mittlere Durchmesser der Ag@Co-Partikel wurde von 5 nm bis 15 nm variiert. Bei der Herstellung von Pt@Co-Teilchen wurde eine unterschiedlich dicke Kobalt-Hülle von ca. 1,0 bis 2,5 nm erzielt. Im Fall des Palladiums wurden sowohl monodispere als auch polydisperse Pd-Nanopartikel mit einer maximal 1,7-2,0nm dicken Kobalthülle synthetisiert. Ein großer Teil dieser Arbeit befasst sich mit den magnetischen Eigenschaften der kolloidalen Teilchen, wobei die SQUID-Magnetometrie und Röntgenzirkulardichroismus (XMCD) dafür eingesetzt wurden. Weil magnetische Messungen alleine nur indirekte Schlüsse über die untersuchten Systeme erlauben, wurde dabei besonderer Wert auf die möglichst genaue strukturelle Charakterisierung der Proben mittels moderner Untersuchungsmethoden gelegt. Röntgendiffraktometrie (XRD), Röntgenabsorptionsfeinstruktur- (EXAFS) und UV-Vis-Spektroskopie sowie Transmissionselektronenmikroskopie (TEM) in Kombination mit Elektronen Energieverlustspektroskopie (EELS) und energiedispersive Röntgenfluoreszensanalyse (EDX) wurden verwendet.
Nanostructured materials are the materials having structural features on the scale of nanometers i.e. 10-9 m. the structural features can enhance the natural properties of the materials or induce additional properties, which are useful for day to technology as well as the future technologies One way to synthesize nanostructured materials is using templating techniques. The templating process involves use of a certain “mould” or “scaffold” to generate the structure. The mould is called as the template, can be a single molecule or assembly of molecule or a larger object, which has its own structure. The product material can be obtained by filling the space around the template with a “precursor”, transformation of precursor into the desired material and then removal of template to get product. The precursor can be any chemical moiety that can be easily transformed in to the desired material. Alternatively the desired material is processed into very tiny bricks or “nano building blocks (NBB)” and the product is obtained by arrangement of the NBB by using a scaffold. We synthesized porous metal oxide spheres of namely TiO2-M2O3: titanium dioxide- M-oxide (M = aluminum, gallium and indium) TiO2-M2O3 and cerium oxide-zirconium oxide solid solution. We used porous polymeric beads as templates. These beads used for chromatographic purposes. For the synthesis of TiO2-M2O3 we used metal- alkoxides as precursor. The pore of beads were filled with precursor and then reacted with water to give transformation of the precursor to amorphous oxide network. The network is crystallized and template is removed by heat treatment at high temperatures. In a similar way we obtained porous spheres of CexZr1-xO2. For this we synthesized nanoparticle of CexZr1-xO2 and used then for the templating process to obtain porous CexZr1-xO2 spheres. Additionally, using the same nanoparticles we synthesized nano-porous powder using self-assembly process between a block-copolymers scaffold and nanoparticles. Morphological and physico-chemical properties of these materials were studies systematically by using various analytical techniques TiO2-M2O3 material were tested for photocatalytic degradation of 2-Chlorophenol a poisonous pollutant. While CexZr1-xO2 spheres were tested for methanol steam reforming reaction to generate hydrogen, which is a fuel for future generation power sources like fuel cells. All the materials showed good catalytic performance.
The present work is dealing with the first synthesis and characterisation of amphiphilic diblock copolymers bearing b-dicarbonyl (acetoacetoxy) chelating residues. Polymers were obtained by Group Transfer Polymerisation (GTP)/acetoacetylation and controlled radical polymerisation techniques (RAFT).Different micellar morphologies of poly(n-butyl methacrylate)-block-poly[2-(acetoacetoxy)ethyl methacrylate] (pBuMA-b-pAEMA) were observed in cyclohexane as a selective solvent. Depending on the block length ratio, either spherical, elliptical, or cylindrical micelles were formed. The density of the polymer chains at the core/corona interface is considerably higher as compared to any other strongly segregating system reported in the literature. It is demonstrated that there are H-bond interactions existing between acetoacetoxy groups, which increase the incompatibility between block segments. In addition, such interactions lead to the formation of secondary structures (such as b-sheets or globular structures) and larger superstructures in the micrometer length scale.Block copolymers were also used to solubilise metal ion salts of different geometries and oxidation states in organic media, in which are otherwise insoluble. Sterically stabilised colloidal hybrid materials are formed, i.e. monodisperse micelles having the metal ion salt incorporated in their core upon complexation with the ligating pAEMA block, whereas pBuMA forms the solvating corona responsible for stabilisation in solution. Systematic studies show that the aggregation behaviour is dependent on different factors, such as the tautomeric form of the beta-dicarbonyl ligand (keto/enol) as well as the nature and amount of added metal ion salt.
The colloidal systems are present everywhere in many varieties such as emulsions (liquid droplets dispersed in liquid), aerosols (liquid dispersed in gas), foam (gas in liquid), etc. Among several new methods for the preparation of colloids, the so-called miniemulsion technique has been shown to be one of the most promising. Miniemulsions are defined as stable emulsions consisting of droplets with a size of 50-500 nm by shearing a system containing oil, water, a surfactant, and a highly water insoluble compound, the so-called hydrophobe 1. In the first part of this work, dynamic crystallization and melting experiments are described which were performed in small, stable and narrowly distributed nanodroplets (confined systems) of miniemulsions. Both regular and inverse systems were examined, characterizing, first, the crystallization of hexadecane, secondly, the crystallization of ice. It was shown for both cases that the temperature of crystallization in such droplets is significantly decreased (or the required undercooling is increased) as compared to the bulk material. This was attributed to a very effective suppression of heterogeneous nucleation. It was also found that the required undercooling depends on the nanodroplet size: with decreasing droplet size the undercooling increases. 2. It is shown that the temperature of crystallization of other n-alkanes in nanodroplets is also significantly decreased as compared to the bulk material due to a very effective suppression of heterogeneous nucleation. A very different behavior was detected between odd and even alkanes. In even alkanes, the confinement in small droplets changes the crystal structure from a triclinic (as seen in bulk) to an orthorhombic structure, which is attributed to finite size effects inside the droplets. An intermediate metastable rotator phase is of less relevance for the miniemulsion droplets than in the bulk. For odd alkanes, only a strong temperature shift compared to the bulk system is observed, but no structure change. A triclinic structure is formed both in bulk and in miniemulsion droplets. 3. In the next part of the thesis it is shown how miniemulsions could be successfully applied in the development of materials with potential application in pharmaceutical and medical fields. The production of cross-linked gelatin nanoparticles is feasible. Starting from an inverse miniemulsion, the softness of the particles can be controlled by varying the initial concentration, amount of cross-link agent, time of cross-linking, among other parameters. Such particles show a thermo-reversible effect, e.g. the particles swell in water above 37 °C and shrink below this temperature. Above 37 °C the chains loose the physical cross-linking, however the particles do not loose their integrity, because of the chemical cross-linking. Those particles have potential use as drug carriers, since gelatin is a natural polymer derived from collagen. 4. The cross-linked gelatin nanoparticles have been used for the biomineralization of hydroxyapatite (HAP), a biomineral, which is the major constituent of our bones. The biomineralization of HAP crystals within the gelatin nanoparticles results in a hybrid material, which has potential use as a bone repair material. 5. In the last part of this work we have shown that layers of conjugated semiconducting polymers can be deposited from aqueous dispersion prepared by the miniemulsion process. Dispersions of particles of different conjugated semiconducting polymers such as a ladder-type poly(para-phenylene) and several soluble derivatives of polyfluorene could be prepared with well-controlled particle sizes ranging between 70 - 250 nm. Layers of polymer blends were prepared with controlled lateral dimensions of phase separation on sub-micrometer scales, utilizing either a mixture of single component nanoparticles or nanoparticles containing two polymers. From the results of energy transfer it is demonstrated that blending two polymers in the same particle leads to a higher efficiency due to the better contact between the polymers. Such an effect is of great interest for the fabrication of opto-electronic devices such as light emitting diodes with nanometer size emitting points and solar cells comprising of blends of electron donating and electron accepting polymers.
Einfache Decarbonylierungen und stereoselektive Oxidationen von Cyclohexadienen und Cyclohexenen
(2001)
Zusammenfassend konnte im Rahmen dieser Arbeit das Synthesepotential von Cyclohexadienen und Cyclohexenen deutlich erweitert werden. Die Darstellung der 1-Alkylcyclohexa-2,5-dien-1-carbonsäuren erfolgte mittels Birch-Reduktion in flüssigem Ammoniak und anschließender Umsetzung der intermediär entstehenden Dianionen mit Alkylhalogeniden. So konnte ausgehend von verschiedenen Benzoesäurederivaten eine Reihe interessanter Cyclohexadiene in sehr guten Ausbeuten synthetisiert werden. Erstmals gelangen säurekatalysierte Decarbonylierungen von Cyclohexadiencarbonsäuren, was die einfache Synthese substituierter Aromaten in ausgezeichneten Ausbeuten ermöglichte. In dieser Arbeit wird der Reaktionsmechanismus vorgestellt, welcher durch den Nachweis von Kohlenmonoxid in der Gasphase der Reaktionslösung durch IR-Spektroskopie untermauert wird. Bei der säurekatalysierten Umsetzung von 3-alkylsubstituierten Cyclohexadien-carbonsäuren entstanden neben den erwarteten Aromaten Lactone in ca. 50% Ausbeute. Schließlich zeigen die untersuchten Singulettsauerstoff-En-Reaktionen, der im ersten Teil dargestellten Cyclohexadiene und Lactone, durchweg hohe Regioselektivitäten und lieferten durch elektrostatische Wechselwirkungen und konformative Effekte zum Teil sehr gute Diastereoselektivitäten. Die auxiliarkontrollierte Photooxygenierungen von Cyclohexenon welches mit verschiedenen Weinsäureestern ketalisiert wurde, zeigten jedoch keine bevorzugte p-Facialität des Singulettsauerstoffs.
Research on monolayers of amphiphilic lipids on aqueous solution is of basic importance in surface science. Due to the applicability of a variety of surface sensitive techniques, floating insoluble monolayers are very suitable model systems for the study of order, structure formation and material transport in two dimensions or the interactions of molecules at the interface with ions or molecules in the bulk (headword 'molecular recognition'). From the behavior of monolayers conclusions can be drawn on the properties of lipid layers on solid substrates or in biological membranes. This work deals with specific and fundamental interactions in monolayers both on the molecular and on the microscopic scale and with their relation to the lattice structure, morphology and thermodynamic behavior of monolayers at the air-water interface. As model system especially monolayers of long chain fatty acids are used, since there the molecular interactions can be gradually adjusted by varying the degree of dissociation by means of the suphase pH value. For manipulating the molecular interactions besides the subphase composition also temperature and monolayer composition are systematically varied. The change in the monolayer properties as a function of an external parameter is analyzed by means of isotherm and surface potential measurements, Brewster-angle microscopy, X-ray diffraction at grazing incidence and polarization modulated infrared reflection absorption spectroscopy. For this a quantitative measure for the molecular interactions and for the chain conformational order is derived from the X-ray data. The most interesting results of this work are the elucidation of the origin of regular polygonal and dendritic domain shapes, the various effects of cholesterol on molecular packing and lattice order of long chain amphiphiles, as well as the detection of an abrupt change in the head group bonding interactions, the chain conformational order and the phase transition pressure between tilted phases in fatty acid monolayers near pH 9. For the interpretation of the latter point a model of the head group bonding structure in fatty acid monolayers as a function of the pH value is developed.