NDLI: Synthesis of dye functionalized xerogels via nucleophilic aromatic substitution of fluoro aromatic compounds with aminosilanes

Content Provider	Springer Nature Link
Author	Seifert, Andreas Ladewig, Katharina Schönherr, Petra Hofmann, Katja Lungwitz, Ralf Roth, Isabelle Pohlers, Andreas Hoyer, Walter Baumann, Gisela Schulze, Steffen Hietschold, Michael Moszner, rbert Burtscher, Peter Spange, Stefan
Copyright Year	2009
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.
Starting Page	328
Ending Page	341
Page Count	14
File Format	PDF
ISSN	09280707
Journal	Journal of Sol-Gel Science and Technology
Volume Number	53
Issue Number	2
e-ISSN	15734846
Language	English
Publisher	Springer US
Publisher Date	2009-10-27
Publisher Place	Boston
Access Restriction	One Nation One Subscription (ONOS)
Subject Keyword	Nucleophilic aromatic substitution reaction Sol–gel process Azo dyes Fluoro aromatic compounds Organic–inorganic hybrid materials Xerogels type II Solid state NMR spectroscopy Nanotechnology Optical and Electronic Materials Inorganic Chemistry Ceramics, Glass, Composites, Natural Methods
Content Type	Text
Resource Type	Article
Subject	Ceramics and Composites Chemistry Materials Chemistry Biomaterials Condensed Matter Physics Electronic, Optical and Magnetic Materials

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