A powerful and concise synthesis of directly linked porphyrin-BODIPY hybrids has been demonstrated, which consists of condensation of directly linked meso-pyrroyl NiII-porphyrin with arylaldehyde, oxidation with p-chloranil, and complexation with BF3⋅Et2O. 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 NiII porphyrins were effectively converted to the corresponding ZnII 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.
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We thank Dr. Zier Yan (Rigaku Beijing Corporation, China) for his help in crystal analysis. The work at Hunan Normal University was supported by the National Natural Science Foundation of China (Grant No. 21272065) and the Scientific Research Foundation for the Returned Overseas Chinese Scholars from State Education Ministry. We thank Dr. Prof. Maeda in Ritusme University for HRMS Analysis. The work at Yonsei University was supported by the Global Research Laboratory Program (2013K1A1A2A0205018 3) funded by the Ministry of Science, ICT & Future, Korea. The quantum calculations were supported by the National Institute of Supercomputing and Network (NISN)/Korea Institute of Science and Technology Information (KISTI) with supercomputing resources including technical support.
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