Synthesis of dye functionalized xerogels via nucleophilic aromatic substitution of fluoro aromatic compounds with aminosilanes |
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Authors: | Andreas Seifert Katharina Ladewig Petra Schönherr Katja Hofmann Ralf Lungwitz Isabelle Roth Andreas Pohlers Walter Hoyer Gisela Baumann Steffen Schulze Michael Hietschold Norbert Moszner Peter Burtscher Stefan Spange |
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Institution: | 1. Institute of Chemistry, Department of Polymer Chemistry, Chemnitz University of Technology, Strasse der Nationen 62, 09111, Chemnitz, Germany 2. Institute of Physics, Department of X-ray and Neutron Diffractometry, Chemnitz University of Technology, Strasse der Nationen 62, 09111, Chemnitz, Germany 3. Institute of Physics, Solid Surface Analysis Group, Chemnitz University of Technology, Strasse der Nationen 62, 09111, Chemnitz, Germany 4. Ivoclar Vivadent AG, Bendererstrasse 2, 9494, Schaan, Liechtenstein, Germany
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Abstract: | The one-pot synthesis of inorganic–organic hybrid materials via combination of sol–gel process and nucleophilic aromatic substitution reaction of various fluoro aromatic compounds and 3-aminopropyltrimethoxysilane has been studied. Both, nucleophilic aromatic substitution reaction and sol–gel process can be accomplished in the same reaction vessel due to the sol–gel precursor tetraethoxysilane acting as solvent during the first reaction step. Hydrogen fluoride, which forms as a by-product of the substitution reaction, is trapped by both silane species present and subsequently serves as catalyst during the sol–gel process. The obtained materials can be classified as type II xerogels, because of the covalent linkage between organic chromophor and inorganic silicon network. Fluoro aromatic compounds with different reactivities for nucleophilic aromatic substitution reactions containing azo, azomethine, and diphenylamine groups were used in order to (1) demonstrate the synthetic concept and (2) fine-tune the optical properties of the resulting chromophoric xerogels. The final chromophor content within the xerogels was varied by modifying the ratio of organosilicon precursor and tetraethoxysilane. All obtained organic–inorganic hybrid materials were characterized in detail using solid state NMR- and UV/vis spectroscopy. Latter one gave experimental confirmation of the partial hydrolysis of azomethine dyes in the xerogels, while no decomposition of azo or diphenylamine dyes was observed. |
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