Synthesis and Characteristics of Organic Reactive Dyes Applied for the Sol-Gel Processing

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We have prepared some 1, 4-naphthoquinones (1) and maleimides (2), as mercocyanine dyes, with a terminal triethoxysilyl group connected directly with a network of Si-O matrix gels in the sol-gel processing. The reactions of 2, 3-dicyano-1, 4-naphthoquinones and maleic anhydrides with amino-propyltriethoxysilane or aminopropylmethyldiethoxysilane gave dyes 1 and 2 with a terminal triethoxysilyl or diethoxysilyl group (yields 22-72%). The absorption spectra of merocyanine dyes with terminal triethoxysilyl group in gel film were different from those in sol, and this result was interpreted by PPP-MO calculations. Dyes with terminal triethoxysilyl group exhibited a higher solubility in ethanol-water mixture. The hydrolysis and condensation of the merocyanine dye were performed under the silica-sol processing conditions to examine the reactivity of terminal triethoxysilyl group.
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