Abstract
The nucleophilic substitution of fluorine of aromatic compounds with n-aminoalkyl trialkoxysilanes and consecutive sol-gel process have been used for the fabrication of various chromophoric sol-gel materials. The displacement of the fluoro substituent of an activated aromatic molecule occurs by a primary or secondary amino group of (CH3O)3Si-(CH2)3-NHR [R- = H-; CH3-, (CH3O)3Si-(CH2)3-] in tetraalkoxysilane or alcohol as solvent and the sol-gel process can be carried in the same vessel. The HF formed is trapped by a tertiary amine and simultaneously serves as the catalyst for the sol-gel process. Various aromatic compounds have been checked for this purpose: 1-(4-fluorophenyl)-2-nitroethylene, 1-(4-fluorophenyl)-2,2-dicyanoethylene, 4-fluorobenzonitrile, 4-fluoronitrobenzene, 4,4′-difluorobenzophenone, 4,4′-difluorobenzil, 7,7′-difluorodibenzylideneacetone, tetrafluoro-p-benzoquinone, and 1,5-difluoro-2,4-dinitrobenzene. Mono and disubstitution has been studied by UV/Vis- and solid state NMR spectroscopy of the xerogels.
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Seifert, A., Spange, S., Müller, H. et al. Fabrication of Chromophoric Xerogels by Synergistic Combination of Nucleophilic Aromatic Substitution and the Sol-Gel Process. Journal of Sol-Gel Science and Technology 26, 77–81 (2003). https://doi.org/10.1023/A:1020789318803
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DOI: https://doi.org/10.1023/A:1020789318803