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

(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(PPh3)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, 1H NMR, 13C 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 CH2Cl2 solution under UV irradiation. Analysis revealed good thermal stability with a decomposition temperature ranging from 301 to 378 °C.

► Novel thiophene derivatives with bis-diarylacrylonitrile were synthesized.
► Photoluminescent spectra of these derivatives were investigated.
► 463–502 nm emission in solid state and 446–491 nm in CH2Cl2 were found.
► The decomposition temperatures of these compounds range from 301 to 378 °C.