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.