Construction of the carbon-chalcogen (S, Se, Te) bond at the 2,6-positions of BODIPY via Stille cross-coupling reaction

Abstract

Seven new 2-chalcogen- or 2,6-dichalcogen- (S, Se, Te) BODIPY derivatives were synthesized in good to excellent yields (55-95%) by a Pd-catalyzed C-heteroatom Stille cross-coupling reaction, overcoming the limitations of SNAr. The fluorophores show interesting tunable optical properties associated with the formation of a twisted intramolecular charge transfer excited state and competing intersystem crossing.