Synthesis of Novel meso-Indole- and meso-Triazatruxene-BODIPY Dyes

Abstract

In this study, the effects of the heteroaromatic indole ring on the chemical and photophysical properties of BODIPY (4,4-difluoro-4-bora-3a,4a-diaza-s-indacene) dyes were investigated. Four BODIPY derivatives with indole rings at the meso- position were synthesized and three of them were converted into the corresponding styryl-derivatives in reasonable yields. To obtain a more complex indole-based trimeric BODIPY derivative in the form of a triazatruxene, several attempts were made by using indole trimerization chemistry and the photophysical studies on the resulting triazatruxene-BODIPY dye revealed a solvent polarity dependent fluorescence behavior, which may be important in the prospective organic electronic applications.