The synthesis and photoluminescence characteristics of novel 4-aryl substituted thiophene derivatives with bis-diarylacrylonitrile unit

Abstract

Abstract (Z)-2-(4-Bromophenyl)-3-(4-(5-((Z)-2-cyano-2-phenylvinyl)thiophen-3-yl)-phenyl)acrylonitrile was synthesized by (Z)-3-(4-(4-formylphenyl)-thiophen-2-yl)-2-phenylacrylonitrile and 2-(4-bromophenyl)acetonitrile through a base catalyzed condensation reaction, and then reacted with various aryl boronic acids under the catalyzing of Pd(PPh 3 ) 4 to afford a series of novel 4-aryl substituted thiophene derivatives with bis-diarylacrylonitrile unit. The structures of the products were characterized using FTIR, 1 H NMR, 13 C NMR, and HRMS. The UV–vis absorption and photoluminescent spectra of these derivatives were investigated. These compounds emit 450–510 nm green fluorescence in the solid state and 446–491 nm emission in CH 2 Cl 2 solution under UV irradiation. Analysis revealed good thermal stability with a decomposition temperature ranging from 301 to 378 °C.