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Institute
- Institut für Chemie (295) (remove)
The underlying motivation for the work carried out for this thesis was the growing need for more sustainable technologies. The aim was to synthesize a “palette” of functional nanomaterials using the established technique of hydrothermal carbonization (HTC). The incredible diversity of HTC was demonstrated together with small but steady advances in how HTC can be manipulated to tailor material properties for specific applications. Two main strategies were used to modify the materials obtained by HTC of glucose, a model precursor representing biomass. The first approach was the introduction of heteroatoms, or “doping” of the carbon framework. Sulfur was for the first time introduced as a dopant in hydrothermal carbon. The synthesis of sulfur and sulfur/nitrogen doped microspheres was presented whereby it was shown that the binding state of sulfur could be influenced by varying the type of sulfur source. Pyrolysis may additionally be used to tune the heteroatom binding states which move to more stable motifs with increasing pyrolysis temperature. Importantly, the presence of aromatic binding states in the as synthesized hydrothermal carbon allows for higher heteroatom retention levels after pyrolysis and hence more efficient use of dopant sources. In this regard, HTC may be considered as an “intermediate” step in the formation of conductive heteroatom doped carbon. To assess the novel hydrothermal carbons in terms of their potential for electrochemical applications, materials with defined nano-architectures and high surface areas were synthesized via templated, as well as template-free routes. Sulfur and/or nitrogen doped carbon hollow spheres (CHS) were synthesized using a polystyrene hard templating approach and doped carbon aerogels (CA) were synthesized using either the albumin directed or borax-mediated hydrothermal carbonization of glucose. Electrochemical testing showed that S/N dual doped CHS and aerogels derived via the albumin approach exhibited superior catalytic performance compared to solely nitrogen or sulfur doped counterparts in the oxygen reduction reaction (ORR) relevant to fuel cells. Using the borax mediated aerogel formation, nitrogen content and surface area could be tuned and a carbon aerogel was engineered to maximize electrochemical performance. The obtained sample exhibited drastically improved current densities compared to a platinum catalyst (but lower onset potential), as well as excellent long term stability. In the second approach HTC was carried out at elevated temperatures (550 °C) and pressure (50 bar), corresponding to the superheated vapor regime (htHTC). It was demonstrated that the carbon materials obtained via htHTC are distinct from those obtained via ltHTC and subsequent pyrolysis at 550 °C. No difference in htHTC-derived material properties could be observed between pentoses and hexoses. The material obtained from a polysaccharide exhibited a slightly lower degree of carbonization but was otherwise similar to the monosaccharide derived samples. It was shown that in addition to thermally induced carbonization at 550 °C, the SHV environment exhibits a catalytic effect on the carbonization process. The resulting materials are chemically inert (i.e. they contain a negligible amount of reactive functional groups) and possess low surface area and electronic conductivity which distinguishes them from carbon obtained from pyrolysis. Compared to the materials presented in the previous chapters on chemical modifications of hydrothermal carbon, this makes them ill-suited candidates for electronic applications like lithium ion batteries or electrocatalysts. However, htHTC derived materials could be interesting for applications that require chemical inertness but do not require specific electronic properties. The final section of this thesis therefore revisited the latex hard templating approach to synthesize carbon hollow spheres using htHTC. However, by using htHTC it was possible to carry out template removal in situ because the second heating step at 550 °C was above the polystyrene latex decomposition temperature. Preliminary tests showed that the CHS could be dispersed in an aqueous polystyrene latex without monomer penetrating into the hollow sphere voids. This leaves the stagnant air inside the CHS intact which in turn is promising for their application in heat and sound insulating coatings. Overall the work carried out in this thesis represents a noteworthy development in demonstrating the great potential of sustainable carbon materials.
The motivation of this work was to investigate the self-assembly of a block copolymer species that attended little attraction before, double hydrophilic block copolymers (DHBCs). DHBCs consist of two linear hydrophilic polymer blocks. The self-assembly of DHBCs towards suprastructures such as particles and vesicles is determined via a strong difference in hydrophilicity between the corresponding blocks leading to a microphase separation due to immiscibility. The benefits of DHBCs and the corresponding particles and vesicles, such as biocompatibility, high permeability towards water and hydrophilic compounds as well as the large amount of possible functionalizations that can be addressed to the block copolymers make the application of DHBC based structures a viable choice in biomedicine. In order to assess a route towards self-assembled structures from DHBCs that display the potential to act as cargos for future applications, several block copolymers containing two hydrophilic polymer blocks were synthesized. Poly(ethylene oxide)-b-poly(N-vinylpyrrolidone) (PEO-b-PVP) and Poly(ethylene oxide)-b-poly(N-vinylpyrrolidone-co-N-vinylimidazole) (PEO-b-P(VP-co-VIm) block copolymers were synthesized via reversible deactivation radical polymerization (RDRP) techniques starting from a PEO-macro chain transfer agent. The block copolymers displayed a concentration dependent self-assembly behavior in water which was determined via dynamic light scattering (DLS). It was possible to observe spherical particles via laser scanning confocal microscopy (LSCM) and cryogenic scanning electron microscopy (cryo SEM) at highly concentrated solutions of PEO-b-PVP. Furthermore, a crosslinking strategy with (PEO-b-P(VP-co-VIm) was developed applying a diiodo derived crosslinker diethylene glycol bis(2-iodoethyl) ether to form quaternary amines at the VIm units. The formed crosslinked structures proved stability upon dilution and transfer into organic solvents. Moreover, self-assembly and crosslinking in DMF proved to be more advantageous and the crosslinked structures could be successfully transferred to aqueous solution. The afforded spherical submicron particles could be visualized via LSCM, cryo SEM and Cryo TEM.
Double hydrophilic pullulan-b-poly(acrylamide) block copolymers were synthesized via copper catalyzed alkyne azide cycloaddition (CuAAC) starting from suitable pullulan alkyne and azide functionalized poly(N,N-dimethylacrylamide) (PDMA) and poly(N-ethylacrylamide) (PEA) homopolymers. The conjugation reaction was confirmed via SEC and 1H-NMR measurements. The self-assembly of the block copolymers was monitored with DLS and static light scattering (SLS) measurements indicating the presence of hollow spherical structures. Cryo SEM measurements could confirm the presence of vesicular structures for Pull-b-PEA block copolymers. Solutions of Pull-b-PDMA displayed particles in cryo SEM. Moreover, an end group functionalization of Pull-b-PDMA with Rhodamine B allowed assessing the structure via LSCM and hollow spherical structures were observed indicating the presence of vesicles, too.
An exemplified pathway towards a DHBC based drug delivery vehicle was demonstrated with the block copolymer Pull-b-PVP. The block copolymer was synthesized via RAFT/MADIX techniques starting from a pullulan chain transfer agent. Pull-b-PVP displayed a concentration dependent self-assembly in water with an efficiency superior to the PEO-b-PVP system, which could be observed via DLS. Cryo SEM and LSCM microscopy displayed the presence of spherical structures. In order to apply a reversible crosslinking strategy on the synthesized block copolymer, the pullulan block was selectively oxidized to dialdehydes with NaIO4. The oxidation of the block copolymer was confirmed via SEC and 1H-NMR measurements. The self-assembled and oxidized structures were subsequently crosslinked with cystamine dihiydrochloride, a pH and redox responsive crosslinker resulting in crosslinked vesicles which were observed via cryo SEM. The vesicular structures of crosslinked Pull-b-PVP could be disassembled by acid treatment or the application of the redox agent tris(2-carboxyethyl)-phosphin-hydrochloride. The successful disassembly was monitored with DLS measurements.
To conclude, self-assembled structures from DHBCs such as particles and vesicles display a strong potential to generate an impact on biomedicine and nanotechnologies. The variety of DHBC compositions and functionalities are very promising features for future applications.
In the present thesis, the self-assembly of multi thermoresponsive block copolymers in dilute aqueous solution was investigated by a combination of turbidimetry, dynamic light scattering, TEM measurements, NMR as well as fluorescence spectroscopy. The successive conversion of such block copolymers from a hydrophilic into a hydrophobic state includes intermediate amphiphilic states with a variable hydrophilic-to-lipophilic balance. As a result, the self-organization is not following an all-or-none principle but a multistep aggregation in dilute solution was observed. The synthesis of double thermoresponsive diblock copolymers as well as triple thermoresponsive triblock copolymers was realized using twofold-TMS labeled RAFT agents which provide direct information about the average molar mass as well as residual end group functionality from a routine proton NMR spectrum. First a set of double thermosensitive diblock copolymers poly(N-n-propylacrylamide)-b-poly(N-ethylacrylamide) was synthesized which differed only in the relative size of the two blocks. Depending on the relative block lengths, different aggregation pathways were found. Furthermore, the complementary TMS-labeled end groups served as NMR-probes for the self-assembly of these diblock copolymers in dilute solution. Reversible, temperature sensitive peak splitting of the TMS-signals in NMR spectroscopy was indicative for the formation of mixed star-/flower-like micelles in some cases. Moreover, triple thermoresponsive triblock copolymers from poly(N-n-propylacrylamide) (A), poly(methoxydiethylene glycol acrylate) (B) and poly(N-ethylacrylamide) (C) were obtained from sequential RAFT polymerization in all possible block sequences (ABC, BAC, ACB). Their self-organization behavior in dilute aqueous solution was found to be rather complex and dependent on the positioning of the different blocks within the terpolymers. Especially the localization of the low-LCST block (A) had a large influence on the aggregation behavior. Above the first cloud point, aggregates were only observed when the A block was located at one terminus. Once placed in the middle, unimolecular micelles were observed which showed aggregation only above the second phase transition temperature of the B block. Carrier abilities of such triple thermosensitive triblock copolymers tested in fluorescence spectroscopy, using the solvatochromic dye Nile Red, suggested that the hydrophobic probe is less efficiently incorporated by the polymer with the BAC sequence as compared to ABC or ACB polymers above the first phase transition temperature. In addition, due to the problem of increasing loss of end group functionality during the subsequent polymerization steps, a novel concept for the one-step synthesis of multi thermoresponsive block copolymers was developed. This allowed to synthesize double thermoresponsive di- and triblock copolymers in a single polymerization step. The copolymerization of different N-substituted maleimides with a thermosensitive styrene derivative (4-vinylbenzyl methoxytetrakis(oxyethylene) ether) led to alternating copolymers with variable LCST. Consequently, an excess of this styrene-based monomer allowed the synthesis of double thermoresponsive tapered block copolymers in a single polymerization step.
Die Arbeit beschreibt die Synthese, Charakterisierung und Anwendung von meso- und mikroporösen Hochleistungspolymeren. Im ersten Teil wird die Synthese von mesoporösen Polybenzimidazol (PBI) auf der Basis einer Templatierungsmethode vorgestellt. Auf der Grundlage kommerzieller Monomere und Silikatnanopartikel sowie eines neuen Vernetzers wurde ein Polymer-Silikat-Hybridmaterial aufgebaut. Das Herauslösen des Silikats mit Ammoniumhydrogendifluorid führt zu mesoporösen Polybenzimidazolen mit spherischen Poren von 9 bis 11 nm Durchmesser. Die Abhängigkeit der beobachteten Porosität vom Massenverhältnis Silikat zu Polymer wurde ebenso untersucht wie die Abhängigkeit der Porosität vom Vernetzergehalt. Die Porosität vollvernetzter Proben zeigt eine lineare Abhängigkeit vom Verhältnis Silikat zu Polymer bis zu einem Grenzwert von 1. Wird der Grenzwert überschritten, ist teilweiser Porenkollaps zu beobachten. Die Abhängigkeit der Porosität vom Vernetzergehalt bei festem Silikatgehalt ist nichtlinear. Oberhalb einer kritischen Vernetzerkonzentration wird eine komplette Replikation der Nanopartikel gefunden. Ist die Vernetzerkonzentration dagegen kleiner als der kritische Wert, so ist der völlige Kollaps einiger Poren bei Stabilität der verbleibenden Poren zu beobachten. Ein komplett unporöses PBI resultiert bei Abwesenheit des Vernetzers. Die mesoporösen PBI-Netzwerke konnten kontrolliert mit Phosphorsäure beladen werden. Die erhaltenen Addukte wurden auf ihre Protonenleitfähigkeit untersucht. Es kann gezeigt werden, dass die Nutzung der vordefinierten Morphologie im Vergleich zu einem unstrukturierten PBI in höheren Leitfähigkeiten resultiert. Durch die vernetzte Struktur war des Weiteren genügend mechanische Stabilität gegeben, um die Addukte reversibel und bei sehr guten Leitfähigkeiten bis zu Temperaturen von 190°C bei 0% relativer Feuchtigkeit zu untersuchen. Dies ist für unstrukturierte Phosphorsäure/PBI - Addukte aus linearem PBI nicht möglich. Im zweiten Teil der Arbeit wird die Synthese intrinsisch mikroporöser Polyamide und Polyimide vorgestellt. Das Konzept intrinsisch mikroporöser Polymere konnte damit auf weitere Polymerklassen ausgeweitet werden. Als zentrales, strukturinduzierendes Motiv wurde 9,9'-Spirobifluoren gewählt. Dieses Molekül ist leicht und vielfältig zu di- bzw. tetrafunktionellen Monomeren modifizierbar. Dabei wurden bestehende Synthesevorschriften modifiziert bzw. neue Vorschriften entwickelt. Ein erster Schwerpunkt innerhalb des Kapitels lag in der Synthese und Charakterisierung von löslichen, intrinsisch mikroporösen, aromatischen Polyamid und Polyimid. Es konnte gezeigt werden, dass das Beobachten von Mikroporosität stark von der molekularen Architektur und der Verarbeitung der Polymere abhängig ist. Die Charakterisierung der Porosität erfolgte unter Nutzung von Stickstoffsorption, Kleinwinkelröntgenstreuung und Molecular Modeling. Es konnte gezeigt werden, dass die Proben stark vom Umgebungsdruck abhängigen Deformationen unterliegen. Die starke Quellung der Proben während des Sorptionsvorgangs konnte durch Anwendung des "dual sorption" Modells, also dem Auftreten von Porenfüllung und dadurch induzierter Henry-Sorption, erklärt werden. Der zweite Schwerpunkt des Kapitels beschreibt die Synthese und Charakterisierung mikroporöser Polyamid- und Polyimidnetzwerke. Während Polyimidnetzwerke auf Spirobifluorenbasis ausgeprägte Mikroporosität und spezifische Oberflächen von ca. 1100 m²/g aufwiesen, war die Situation für entsprechende Polyamidnetzwerke abweichend. Mittels Stickstoffsorption konnte keine Mikroporosität nachgewiesen werden, jedoch konnte mittels SAXS eine innere Grenzfläche von ca. 300 m²/g nachgewiesen werden. Durch die in dieser Arbeit gezeigten Experimente kann die Grenze zwischen Polymeren mit hohem freien Volumen und mikroporösen Polymeren somit etwas genauer gezogen werden. ausgeprägte Mikroporosität kann nur in extrem steifen Strukturen nachgewiesen werden. Die Kombination der Konzepte "Mesoporosität durch Templatierung" und "Mikroporosität durch strukturierte Monomere" hatte ein hierarchisch strukturiertes Polybenzimidazol zum Ergebnis. Die Präsenz einer Strukturierung im molekularen Maßstab konnte SAXS bewiesen werden. Das so strukturierte Polybenzimidazol zeichnete sich durch eine höhere Protonenleitfähigkeit im Vergleich zu einem rein mesoporösen PBI aus. Der letzte Teil der Arbeit beschäftigte sich mit der Entwicklung einer neuen Synthesemethode zur Herstellung von Polybenzimidazol. Es konnte gezeigt werden, dass lineares PBI in einer eutektischen Salzschmelze aus Lithium- und Kaliumchlorid synthetisiert werden kann. Die Umsetzung der spirobifluorenbasierten Monomere zu löslichem oder vernetztem PBI ist in der Salzschmelze möglich.
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.
Die vorliegende Arbeit behandelt die Synthese und Charakterisierung von funktionalisierten Alkydharzen und die photoinduzierte Polymerisation dieser unter Einsatz einer Quecksilberdampflampe oder einer UV LED mit unterschiedlicher Lichtintensität. Der Fokus dieser Arbeit bestand in der gezielten Substitution der internalen Doppelbindungen der Fettsäureester durch reaktivere Gruppen, wie Acrylate oder Methacrylate, welche für Alkydharze in dieser Form so in der Literatur nicht beschrieben sind. Untersuchungen des Polymerisationsverhaltens dieser funktionalisierten Harze wurden mit der Photo DSC durchgeführt, wobei Bis – (4 – methoxybenzoyl) diethylgermanium als Photoinitiator diente. Die Ergebnisse haben gezeigt, dass die Harze radikalisch polymerisiert werden können und eine geringere Abhängigkeit von der Umgebungsatmosphäre (Luftsauerstoff bzw. Stickstoff) vorliegt. Dies ist so in der Literatur für funktionalisierte Alkydharze nicht bekannt. Abmischungen von unterschiedlichen Monomeren und funktionalisierten Harzen bewirkten eine Steigerung der Viskosität sowie eine Verringerung der Sauerstoffinhibierung im Zuge der photoinduzierten Polymerisation unter Luftsauerstoff für die Quecksilberdampflampe und der UV LED.
Zur Untersuchung der sauerstoffinhibierenden Wirkung der Harze sind Synthesen unterschiedlicher, funktionalisierter Ölsäuremethylester als Modellsubstanzen durchgeführt worden. Ein verbessertes Polymerisationsverhalten und eine geringe Abhängigkeit von der Umgebungsatmosphäre konnte für die Modelle nachgewiesen werden. Zur Aufklärung des verbesserten Polymerisationsverhaltens sind gezielt Substituenten (Imidazol, Brom, Alkohol, Acetat) in den funktionalisierten Ölsäuremethylester eingebaut worden, um den Einfluss dieser aufzuzeigen. Im Rahmen dieser Synthesen sind neuartige Strukturen synthetisiert worden, welche so in der Literatur nicht beschrieben sind. Die Gegenüberstellung der Polymerisationszeit, der Umsatz der (Meth-)Acrylatgruppen sowie die Zeit zum Erreichen der maximalen Polymerisationsgeschwindigkeit unter Verwendung von unterschiedlichen UV Lichtquellen hat einen Einfluss der Substituenten auf das Polymerisationsverhalten gezeigt.
The growing energy demand of the modern economies leads to the increased consumption of fossil fuels in form of coal, oil, and natural gases, as the mains sources. The combustion of these carbon-based fossil fuels is inevitably producing greenhouse gases, especially CO2. Approaches to tackle the CO2 problem are to capture it from the combustion sources or directly from air, as well as to avoid CO2 production in energy consuming sources (e.g., in the refrigeration sector). In the former, relatively low CO2 concentrations and competitive adsorption of other gases is often leading to low CO2 capacities and selectivities. In both approaches, the interaction of gas molecules with porous materials plays a key role. Porous carbon materials possess unique properties including electric conductivity, tunable porosity, as well as thermal and chemical stability. Nevertheless, pristine carbon materials offer weak polarity and thus low CO2 affinity. This can be overcome by nitrogen doping, which enhances the affinity of carbon materials towards acidic or polar guest molecules (e.g., CO2, H2O, or NH3). In contrast to heteroatom-free materials, such carbon materials are in most cases “noble”, that is, they oxidize other matter rather than being oxidized due to the very positive working potential of their electrons. The challenging task here is to achieve homogenous distribution of significant nitrogen content with similar bonding motives throughout the carbon framework and a uniform pore size/distribution to maximize host-guest interactions. The aim of this thesis is the development of novel synthesis pathways towards nitrogen-doped nanoporous noble carbon materials with precise design on a molecular level and understanding of their structure-related performance in energy and environmental applications, namely gas adsorption and electrochemical energy storage.
A template-free synthesis approach towards nitrogen-doped noble microporous carbon materials with high pyrazinic nitrogen content and C2N-type stoichiometry was established via thermal condensation of a hexaazatriphenylene derivative. The materials exhibited high uptake of guest molecules, such as H2O and CO2 at low concentrations, as well as moderate CO2/N2 selectivities. In the following step, the CO2/N2 selectivity was enhanced towards molecular sieving of CO2 via kinetic size exclusion of N2. The precise control over the condensation degree, and thus, atomic construction and porosity of the resulting materials led to remarkable CO2/N2 selectivities, CO2 capacities, and heat of CO2 adsorption. The ultrahydrophilic nature of the pore walls and the narrow microporosity of these carbon materials served as ideal basis for the investigation of interface effects with more polar guest molecules than CO2, namely H2O and NH3.
H2O vapor physisorption measurements, as well as NH3-temperature programmed desorption and thermal response measurements showed exceptionally high affinity towards H2O vapor and NH3 gas. Another series of nitrogen-doped carbon materials was synthesized by direct condensation of a pyrazine-fused conjugated microporous polymer and their structure-related performance in electrochemical energy storage, namely as anode materials for sodium-ion battery, was investigated.
All in all, the findings in this thesis exemplify the value of molecularly designed nitrogen-doped carbon materials with remarkable heteroatom content implemented as well-defined structure motives. The simultaneous adjustment of the porosity renders these materials suitable candidates for fundamental studies about the interactions between nitrogen-doped carbon materials and different guest species.
Hepcidin-25 (Hep-25) plays a crucial role in the control of iron homeostasis. Since the dysfunction of the hepcidin pathway leads to multiple diseases as a result of iron imbalance, hepcidin represents a potential target for the diagnosis and treatment of disorders of iron metabolism. Despite intense research in the last decade targeted at developing a selective immunoassay for iron disorder diagnosis and treatment and better understanding the ferroportin-hepcidin interaction, questions remain. The key to resolving these underlying questions is acquiring exact knowledge of the 3D structure of native Hep-25. Since it was determined that the N-terminus, which is responsible for the bioactivity of Hep-25, contains a small Cu(II)-binding site known as the ATCUN motif, it was assumed that the Hep-25-Cu(II) complex is the native, bioactive form of the hepcidin. This structure has thus far not been elucidated in detail. Owing to the lack of structural information on metal-bound Hep-25, little is known about its possible biological role in iron metabolism. Therefore, this work is focused on structurally characterizing the metal-bound Hep-25 by NMR spectroscopy and molecular dynamics simulations. For the present work, a protocol was developed to prepare and purify properly folded Hep-25 in high quantities. In order to overcome the low solubility of Hep-25 at neutral pH, we introduced the C-terminal DEDEDE solubility tag. The metal binding was investigated through a series of NMR spectroscopic experiments to identify the most affected amino acids that mediate metal coordination. Based on the obtained NMR data, a structural calculation was performed in order to generate a model structure of the Hep-25-Ni(II) complex. The DEDEDE tag was excluded from the structural calculation due to a lack of NMR restraints. The dynamic nature and fast exchange of some of the amide protons with solvent reduced the overall number of NMR restraints needed for a high-quality structure. The NMR data revealed that the 20 Cterminal Hep-25 amino acids experienced no significant conformational changes, compared to published results, as a result of a pH change from pH 3 to pH 7 and metal binding. A 3D model of the Hep-25-Ni(II) complex was constructed from NMR data recorded for the hexapeptideNi(II) complex and Hep-25-DEDEDE-Ni(II) complex in combination with the fixed conformation of 19 C-terminal amino acids. The NMR data of the Hep-25-DEDEDE-Ni(II) complex indicates that the ATCUN motif moves independently from the rest of the structure. The 3D model structure of the metal-bound Hep-25 allows for future works to elucidate hepcidin’s interaction with its receptor ferroportin and should serve as a starting point for the development of antibodies with improved selectivity.
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.
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.