Porphyrin–Azobenzene–Bodipy Triads: Syntheses, Structures, and Photophysical Properties

Cyclic and acyclic azobenzene bridged porphyrin−dipyrrin derivatives were successfully prepared via Suzuki−Miyaura coupling reaction of α,α′-diborylated dipyrromethane with bromoazophenyl porphyrin or reaction of borylated porphyrin with dibromoazophenyl dipyrrin, and the corresponding porphyrin−Bodipy derivatives were obtained by subsequent boron complexation. The cyclic porphyrin−dipyrrin compound 3Ni was confirmed by X-ray diffraction. The low fluorescence quantum yields of azobenzene bridged porphyrin−Bodipy can be ascribed to the presence of the intramolecular charge transfer state.