Strategic Construction of Directly Linked Porphyrin-BODIPY Hybrids

A powerful and concise synthesis of directly linked porphyrin-BODIPY hybrids has been demonstrated, which consists of condensation of directly linked meso-pyrroyl Ni^II -porphyrin with arylaldehyde, oxidation with p-chloranil, and complexation with BF₃ ⋅Et₂ O. Synthesized hybrids include porphyrin dimer 6Ni, trimers 8Ni, 9Ni, tetramer 12Ni, pentamer 16Ni, hexamer 13Ni, and nonamers 17Ni and 18Ni. The structures of 6Ni, 9Ni and 12Ni were unambiguously confirmed by X-ray diffraction analysis. Some Ni^II porphyrins were effectively converted to the corresponding Zn^II porphryins. In these hybrids, the pigments are three-dimensionally arranged with a face-to-face dimeric porphyrin unit in a well-defined manner, featuring their potential as light-harvesting antenna and functional hosts.