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Institute
- Institut für Chemie (3503) (remove)
Driven mostly by the search for chemical syntheses under biocompatible conditions, so called "click" chemistry rapidly became a growing field of research. The resulting simple one-pot reactions are so far only scarcely accompanied by an adequate optimization via comparably straightforward and robust analysis techniques possessing short set-up times. Here, we report on a fast and reliable calibration-free online NMR monitoring approach for technical mixtures. It combines a versatile fluidic system, continuous-flow measurement of H-1 spectra with a time interval of 20 s per spectrum, and a robust, fully automated algorithm to interpret the obtained data. As a proof-of-concept, the thiol-ene coupling between N-boc cysteine methyl ester and ally] alcohol was conducted in a variety of non-deuterated solvents while its time-resolved behaviour was characterized with step tracer experiments. Overlapping signals in online spectra during thiol-ene coupling could be deconvoluted with a spectral model using indirect hard modeling and were subsequently converted to either molar ratios (using a calibration free approach) or absolute concentrations (using 1-point calibration). For various solvents the kinetic constant k for pseudo-first order reaction was estimated to be 3.9 h(-1) at 25 degrees C. The obtained results were compared with direct integration of non-overlapping signals and showed good agreement with the implemented mass balance. (C) 2017 Elsevier Inc. All rights reserved.
Ionic liquids are well known for their high gas absorption capacity. It is shown that this is not a solvent constant, but can be enhanced by another factor of 10 by pore confinement, here of the ionic liquid (IL) 1-ethyl-3-methylimidazolium acetate (EmimOAc) in the pores of carbon materials. A matrix of four different carbon compounds with micro- and mesopores as well as with and without nitrogen doping is utilized to investigate the influence of the carbons structure on the nitrogen uptake in the pore-confined EmimOAc. In general, the absorption is most improved for IL in micropores and in nitrogen-doped carbon. This effect is so large that it is already seen in TGA and DSC experiments. Due to the low vapor pressure of the IL, standard volumetric sorption experiments can be used to quantify details of this effect. It is reasoned that it is the change of the molecular arrangement of the ions in the restricted space of the pores that creates additional free volume to host molecular nitrogen.
The aim of this study was to develop a one-step synthesis of gold nanotriangles (NTs) in the presence of mixed phospholipid vesicles followed by a separation process to isolate purified NTs. Negatively charged vesicles containing AOT and phospholipids, in the absence and presence of additional reducing agents (polyampholytes, polyanions or low molecular weight compounds), were used as a template phase to form anisotropic gold nanoparticles. Upon addition of the gold chloride solution, the nucleation process is initiated and both types of particles, i.e., isotropic spherical and anisotropic gold nanotriangles, are formed simultaneously. As it was not possible to produce monodisperse nanotriangles with such a one-step procedure, the anisotropic nanoparticles needed to be separated from the spherical ones. Therefore, a new type of separation procedure using combined polyelectrolyte/micelle depletion flocculation was successfully applied. As a result of the different purification steps, a green colored aqueous dispersion was obtained containing highly purified, well-defined negatively charged flat nanocrystals with a platelet thickness of 10 nm and an edge length of about 175 nm. The NTs produce promising results in surface-enhanced Raman scattering.
Somewhat surprisingly, inverted ("O-down") CO adsorbates on NaCl(100) were recently observed experimentally after infrared vibrational excitation (Lau et al., Science, 2020, 367, 175-178). Here we characterize these species using periodic density functional theory and a quantum mechanical description of vibrations. We determine stationary points and minimum energy paths for CO inversion, for low (1/8 and 1/4 monolayers (ML)) and high (1 ML) coverages. Transition state theory is applied to estimate thermal rates for "C-down" to "O-down" isomerization and the reverse process. For the 1/4 ML p(1 x 1) structure, two-dimensional and three-dimensional potential energy surfaces and corresponding anharmonic vibrational eigenstates obtained from the time-independent nuclear Schrodinger equation are presented. We find (i) rather coverage-independent CO inversion energies (of about 0.08 eV or 8 kJ mol(-1) per CO) and corresponding classical activation energies for "C-down" to "O-down" isomerization (of about 0.15 eV or 14 kJ mol(-1) per CO); (ii) thermal isomerization rates at 22 K which are vanishingly small for the "C-down" to "O-down" isomerization but non-negligible for the back reaction; (iii) several "accidentally degenerate" pairs of eigenstates well below the barrier, each pair describing "C-down" to "O-down" localized states.
This paper focuses on two different strategies to incorporate gold nanoparticles (AuNPs) into the matrix of polyacrylamide (PAAm) hydrogels. Poly(ethyleneimine) (PEI) is used as both reducing and stabilizing agent for the formation of AuNPs. In addition, the influence of an ionic liquid (IL) (i.e., 1-ethyl-3-methylimidazolium ethylsulfate) on the stability of the nanoparticles and their immobilization in the hydrogel is investigated The results show that AuNPs surrounded by a shell containing PEI and IL, synthesized according to the one-pot approach, are much better immobilized within the PAAm hydrogel. Hereby, the IL is responsible for structural changes in the hydrogel as well as the improved stabilization and embedding of the AuNPs into the polymer gel matrix.
Nanostructured inorganic materials are routinely synthesized by the use of templates. Depending on the synthesis conditions of the product material, either “soft” or “hard” templates can be applied. For sol-gel processes, usually “soft” templating techniques are employed, while “hard” templates are used for high temperature synthesis pathways. In classical templating approaches, the template has the unique role of structure directing agent, in the sense that it is not participating to the chemical formation of the resulting material. This work investigates a new templating pathway to nanostructured materials, where the template is also a reagent in the formation of the final material. This concept is described as “reactive templating” and opens a synthetic path toward materials which cannot be synthesised on a nanometre scale by classical templating approaches. Metal nitrides are such kind of materials. They are usually produced by the conversion of metals or metal oxides in ammonia flow at high temperature (T > 1000°C), which make the application of classical templating techniques difficult. Graphitic carbon nitride, g-C3N4, despite its fundamental and theoretical importance, is probably one of the most promising materials to complement carbon in material science and many efforts are put in the synthesis of this material. A simple polyaddition/elimination reaction path at high temperature (T = 550°C) allows the polymerisation of cyanamide toward graphitic carbon nitride solids. By hard templating, using nanostructured silica or aluminium oxide as nanotemplates, a variety of nanostructured graphitic carbon nitrides such as nanorods, nanotubes, meso- and macroporous powders could be obtained by nanocasting or nanocoating. Due to the special semi-conducting properties of the graphitic carbon nitride matrix, the nanostructured graphitic carbon nitrides show unexpected catalytic activity for the activation of benzene in Friedel-Crafts type reactions, making this material an interesting metal free catalyst. Furthermore, due to the chemical composition of g-C3N4 and the fact that it is totally decomposed at temperatures between 600°C and 800°C even under inert atmosphere, g-C3N4 was shown to be a good nitrogen donor for the synthesis of early transition metal nitrides at high temperatures. Thus using the nanostructured carbon nitrides as “reactive templates” or “nanoreactors”, various metal nitride nanostructures, such as nanoparticles and porous frameworks could be obtained at high temperature. In this approach the carbon nitride nanostructure played both the role of the nitrogen source and of the exotemplate, imprinting its size and shape to the resulting metal nitride nanostructure.
Cryo-electron microscopy, atomic force microscopy, and light microscopy investigations provide experimental evidence that amphiphilic emulsion copolymerization particles change their morphology in dependence on concentration. The shape of the particles is spherical at solids content above 1%, but it changes to rod-like, ring-like, and web-like structures at lower concentrations. In addition, the shape and morphology of these particles at low concentrations are not fixed but very flexible and vary with time between spheres, flexible pearlnecklace structures, and stretched rods.
The fruit of Aristotelia chilensis is considered a "super fruit" due to its high concentration of polyphenols displaying exceptional antioxidant capacities ORAC. From maqui berries have been reported several anthocyanins and glycosylated flavonoids, those benefits increase the attention to restudy the plant. From the leaves of A. chilensis several indole alkaloids have been reported, we in addition to aristoteline, aristone, aristoquinoline and 3-fromylindole report the spectroscopic elucidation of 8-oxo-9-dehydromakomakine (1), hobartine (2) and a new alkaloid named 8-oxohobartine (3). Compound 1 to 3 did not show bactericidal activity against E. coli and S. aureus till 200 mu g.
Lobelia tupa, also called devil's tobacco, is a native plant from the center-south of Chile which has been used by the native people of Chile as a hallucinogenic and anesthetic plant. A new piperidine alkaloid, called pentylsedinine, which comprises five carbons in the side chain, was isolated from the aerial part of L. tupa, along with lobeline and lobelanidine. The structure was established on the basis of 1D and 2D NMR spectroscopy. While lobeline is a neutral antagonist at alpha 3 beta 2/alpha 3 beta 4 nAChR and alpha 7 nAChR, both lobelanidine and pentylsedinine act as partial agonists at nAChR
The spatial magnetic properties (Through-Space NMR Shieldings-TSNMRS) of already synthesized dehydro[n]annulenes of various ring size (from C-12 to C-20) have been computed, visualized as Isochemical Shielding Surfaces (ICSS) of various size and direction, and were examined subject to present (anti)aromaticity. For this purpose the thus quantified ring current effect of the macro cycles on proximate protons in proton NMR spectra was employed.
Molecular excitons play a central role in processes of solar energy conversion, both natural and artificial. It is therefore no wonder that numerous experimental and theoretical investigations in the last decade, employing state-of-the-art spectroscopic techniques and computational methods, have been driven by the common aim to unravel exciton dynamics in multichromophoric systems. Theoretically, exciton (de)localization and transfer dynamics are most often modelled using either mixed quantum-classical approaches (e.g., trajectory surface hopping) or fully quantum mechanical treatments (either using model diabatic Hamiltonians or direct dynamics). Yet, the terms such as "exciton localization" or "exciton transfer" may bear different meanings in different works depending on the method in use (quantum-classical vs. fully quantum). Here, we relate different views on exciton (de)localization. For this purpose, we perform molecular surface hopping simulations on several tetracene dimers differing by a magnitude of exciton coupling and carry out quantum dynamical as well as surface hopping calculations on a relevant model system. The molecular surface hopping simulations are done using efficient long-range corrected time-dependent density functional tight binding electronic structure method, allowing us to gain insight into different regimes of exciton dynamics in the studied systems.
We dissect the sources of error leading to inaccuracies in the description of the geometry and optical excitation energies of pi-conjugated polymers. While the ground-state bond length alternation is shown to be badly reproduced by standard functionals, the recently adapted functionals PBEh* and omega PBE* as well as the double hybrid functional XYGJ-OS manage to replicate results obtained at the CCSD(T) level. By analysis of the bond length alternation in the excited state, a sensitive dependence of the exciton localization on the long-range behavior of the functional and the amount of Hartree-Fock exchange present is shown. Introducing thermal disorder through molecular dynamics simulations allows the consideration of a range of thermally accessible configurations of each oligomer, including trans to cis rotations, which break the conjugation of the backbone. Thermal disorder has a considerable effect when combined with functionals that overestimate the delocalization of the excitation, such as B3LYP. For functionals with a larger amount of exact exchange such as our PBEh* and omega PBE*, however, the effect is small, as excitations are often localized enough to fit between twists in the chain.
A series of new N2S2 mixed ligand transition metal complexes, where N-2 is phenanthroline and S-2 is 1,2- dithiooxalate (dto) or 1,2-dithiosquarate (dtsq), has been synthesized and characterized. IR spectra reveal that the 1,2- dithiolate ligands are coordinated via the sulfur atoms forming a N2S2 coordination sphere. The copper(II) complex [Cu(phen)(dto)] was studied by EPR spectroscopy as a diamagnetically diluted powder. The diamagnetic dilution resulted from doping of the copper complex into the isostructural host lattice of the nickel complex [Ni(phen)(dto)]. The electronic situation in the frontier orbitals of the copper complex calculated from the experimental data is compared to the results of EHT and DFT calculations. Furthermore, one side product, chlorobis(1,10-phenanthroline)copper(I) ethanol solvate hydrate [(phen)(2)CuCl]center dot C2H5OH center dot H2O, was formed by a reduction process and characterized by X-ray diffraction. In the crystal packing one-dimensional columns of dimers are formed, stabilized by significant pi-pi interactions.
A series of new monocationic iridium(III) complexes [Ir((CN)-N-boolean AND)(2)((NN)-N-boolean AND)]PF6 with "large-surface" alpha,alpha'-diimin ligands (NN)-N-boolean AND (dap = 1,12-diazaperylene, dmedap = 2,11-dimethyl-1,12-diazaperylene, dipdap = 2,11-diisopropyl-1,12-diazaperylene) and different cyclometalating ligands (CN)-N-boolean AND (piq = 1-phenylisoquinoline, bzq = benzo[h]quinoline, ppz = 1-phenylpyrazole, thpy = 2-(2-thienyl)pyridine, ppy = 2-phenylpyridine, meppy = 2-(4-methylphenyl)pyridine, dfppy = 2-(2,4-difluorophenyl)pyridine) were synthesized. The solid structures of the complexes [Ir(piq)(2)(dap)]PF6, [Ir(bzq)(2)(dap)]PF6, [Ir(ppy)(2)(dipdap)]PF6, [Ir(piq)(2)(dmedap)]PF6, [Ir(ppy)(2)(dap)]PF6 and [Ir(ppz)(2)(dap)]PF6 are reported. In [Ir(piq)(2)(dap)]PF6, the dap ligand and one of the piq ligands of each cationic complex are involved in pi-pi stacking interactions forming supramolecular channels running along the crystallographic c axis. In the crystalline [Ir(bzq)(2)(dap)]PF6 pi-pi stacking interactions between the metal complexes lead to the formation of a 2D layer structure. In addition, CH-pi interactions were found in all compounds, which are what stabilizes the solid structure. In particular, a significant number of them were found in [Ir(piq)(2)(dap)]PF6 and [Ir(bzq)(2)(dap)]PF6. The crystal structures of [Ir(ppy)(2)(dipdap)]PF6 and [Ir(ppy)(2)(dmedap)]PF6 are also presented, being the first examples of bis-cyclometalated iridium(III) complexes with phenanthroline-type alpha,alpha'-diimin ligands bearing bulky alkyl groups in the neighbourhood of the N-donor atoms. These ligands implicate a distorted octahedral coordination geometry that in turn destabilized the Ir-N-N boolean AND N bonds. The new iridium (III) complexes are not luminescent. All compounds show an electrochemically irreversible anodic peak between 1.15 and 1.58 V, which is influenced by the different cyclometalated ligands. All of the new complexes show two reversible successive one-electron "large-surface" ligand-centred reductions around -0.70 V and -1.30 V. Electrospray ionisation mass spectrometry (ESI-MS) and collision induced decomposition (CID) measurements were used to investigate the stability of the new complexes. Thereby, the stability agreed well with the order of the Ir-N-N boolean AND N bond lengths.
Herein, we represent cation-responsive fluorescent probes for the divalent cations Zn2+, Mg2+ and Ca2+, which show cation-induced fluorescence enhancements (FE) in water. The Zn2+-responsive probes Zn1, Zn2, Zn3 and Zn4 are based on o-aminoanisole-N,N-diacetic acid (AADA) derivatives and show in the presence of Zn2+ FE factors of 11.4, 13.9, 6.1 and 8.2, respectively. Most of all, Zn1 and Zn2 show higher Zn2+ induced FE than the regioisomeric triazole linked fluorescent probes Zn3 and Zn4, respectively. In this set, ZN2 is the most suitable probe to detect extracellular Zn2+ levels. For the Mg2+-responsive fluorescent probes Mg1, Mg2 and Mg3 based on o-aminophenol-N,N,O-triacetic acid (APTRA) derivatives, we also found that the regioisomeric linkage influences the fluorescence responds towards Mg2+ (Mg1+100 mM Mg2+ (FEF=13.2) and Mg3+100 mM Mg2+ (FEF=2.1)). Mg2 shows the highest Mg2+-induced FE by a factor of 25.7 and an appropriate K-d value of 3 mM to measure intracellular Mg2+ levels. Further, the Ca2+-responsive fluorescent probes Ca1 and Ca2 equipped with a 1,2-bis(o-aminophenoxy)ethane-N,N,N',N'-tetraacetic acid (BAPTA) derivative show high Ca2+-induced FEs (Ca1 (FEF=22.1) and Ca2 (FEF=23.0)). Herein, only Ca1 (K-d=313 nM) is a suitable Ca2+ fluorescent indicator to determine intracellular Ca2+ levels.
Indium(III) chloride forms in water with potassium 1,2-dithiooxalate (dto) and potassium 1,2-dithiosquarate (dtsq) stable coordination compounds. Due to the higher bridging ability of the 1,2-dithiooxalate ligand in all cases only thiooxalate bridged binuclear complexes were found. From 1,2-dithioquadratate with an identical donor atom set mononuclear trischelates could be isolated. Five crystalline complexes, (BzlMe(3)N)(4)[(dto)(2)In(dto)In(dto)(2)] (1), (BzlPh(3)P)(4)[(dto)(2)In(dto)In(dto)(2)] (2), (BzlMe(3)N)(3)[In(dtsq)(3)] (3), (Bu4N)(3)[In(dtsq)(3)] (4) and (Ph4P)[In(dtsq)(2)(DMF)(2)] (5), have been isolated and characterized by X-ray analyses. Due to the type of the complex and the cations involved these compounds crystallize in different space groups with the following parameters: 1, monoclinic in P2(1)/c with a = 14.4035(5) Angstrom, b = 10.8141(5) Angstrom, c = 23.3698(9) Angstrom, beta = 124.664(2)degrees, and Z = 2; 2, triclinic in P (1) over bar with a = 11.3872(7) Angstrom, b = 13.6669(9) Angstrom, c = 17.4296(10) Angstrom, alpha = 88.883(5)degrees, beta = 96.763(1)degrees, gamma = 74.587(5)degrees, and Z = 1; 3, hexagonal in R3 with a = 20.6501(16) Angstrom, b = 20.6501(16) Angstrom, c = 19.0706(13) Angstrom and Z = 6; 4, monoclinic in P21/c with a = 22.7650(15) Angstrom, b = 20.4656(10) Angstrom, c = 14.4770(9) Angstrom, P
The first Si-H-containing azasilaheterocycle, 1,3-dimethyl-3-silapiperidine 1, was synthesized, and its molecular structure and conformational properties were studied by gas-phase electron diffraction (GED), low temperature NMR, IR and Raman spectroscopy and quantum chemical calculations. The compound exists as a mixture of two conformers possessing the chair conformation with the equatorial NMe group and differing by axial or equatorial position of the SiMe group. In the gas phase, the SiMeax conformer predominates (GED: ax/eq = 65(7):35(7)%,Delta G = 0.36(18) kcal/mol; IR: ax/eq = 62(5):38(5)%,Delta G = 0.16(7) kcal/mol). In solution, at 143 k the SiMeeq conformer predominates' in the frozen equilibrium (NMR: ax/eq = 31.5(1.5):68.5(1.5)%, Delta G = -0.22(2) kcal/mol). Thermodynamic parameters of the ring inversion are determined (Delta G(double dagger) = 8.9-9.0 kcal/mol, Delta H-double dagger = 9.6 kcal/mol, Delta S-double dagger = 2.1 eu). High-level quantum chemical calculations :(MP2, G2, CCSD(T)) nicely reproduce the experimental geometry and the predominance of the axial conformer in the gas phase.
1-Methylthio-1-phenyl-1-silacyclohexane 1, the first silacyclohexane with the sulfur atom at silicon, was synthesized and its molecular structure and conformational preferences studied by gas-phase electron diffraction (GED) and low temperature C-13 and Si-29 NMR spectroscopy (LT NMR). Quantum-chemical calculations were carried out both for the isolated species and solvate complexes in gas and in polar medium. The predominance of the 1-MeSaxPheq conformer in gas phase (1-Ph-eq :1-Ph-ax = 55:45, Delta G degrees = 0.13 kcal/mol) determined from GED is consistent with that measured in the freon solution by LT NMR (1-Ph-eq:1-Ph-ax = 65:35, Delta G degrees = 0.12 kcal/mol), the experimentally measured ratios being close to that estimated by quantum chemical calculations at both the DFT and MP2 levels of theory. (C) 2019 Elsevier Ltd. All rights reserved.