Reaction of perylene-3,4,9,10-tetracarboxylic acid dianhydride with 3-aminopropyltriethoxysilane and hexamethyldisilazane

Abstract

The reaction of perylene-3,4,9,10-tetracarboxylic acid dianhydride with 3-aminopropyltriethoxysilane and hexamethyldisilazane was investigated. A possibility of obtaining a new dye resistant to UV light and heating (up to 300°C), consisting of structural fragments of perylene-3,4,9,10-tetracarboxydiimede, diethoxysiloxane, and 3-aminopropylethoxysiloxane was demonstrated. A compound obtained in 43% yield by heating (7 h, 180–200°C) perylene-3,4,9,10-tetracarboxylic acid dianhydride with excess 3-aminopropyltriethoxysilane in the presence of catalytic amounts of zinc acetate is an oligomer appropriate for the solgel process, displays strong luminescence in the red spectral region (540–620 nm), and has good film-forming properties. The participation of hexamethyldisilazane consists in binding water molecules formed in the reaction of perylene-3,4,9,10-tetracarboxylic acid dianhydride with 3-aminopropyltriethoxysilane and in the formation of trimethylsilanol which replaces a part of the EtO groups at the silicon atoms by a more bulky Me₃SiO groups, causing significant increase in the solubility of the dye in organic solvents and silicon sol-gel monomers. The hydrolysis of silicon-containing dye and subsequent dehydration of the resulting gel lead to the formation of insoluble xerogel.