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m-Pyripentaphyrins(1.0.0.0.0): BIII Complexes and β-β Directly Linked Dimers
1Key Laboratory of Chemical Biology and Traditional Chinese Medicine, Ministry of Educational of China, Key Laboratory of the Assembly and Application of Organic Functional Molecules of Hunan Province, College of Chemistry and Chemical Engineering, Hunan Normal University, Changsha, 410081, China.
Abstract:
m-Pyripentaphyrins(1.0.0.0.0) were synthesized by Suzuki-Miyaura coupling of 3,5-bis(5-borylpyrrol-2-yl)-BODIPY with 2,6-dibromopyridine. Upon treatment with PhBCl2, pyripentaphyrin 1 provided mono- and bis-BIII complexes sequentially. The Mono-BIII complex shows a distorted tetrahedral coordinated BIII with a σ-phenyl ligand on the BIII and the bis-BIII complex shows an additional distorted tetrahedral coordinated BIII with a B-H bond. Bromination of the pyripentaphyrins with N-bromosuccinimide (NBS) resulted in regioselective formation of 8-bromopyripentaphyrins, which were dimerized to 8,8'-linked dimers by reductive coupling with Ni(cod)2. While all these pyripentaphyrins are nonaromatic, they exhibit characteristic broad absorption bands at long wavelength near the NIR region, indicating the presence of effective macrocyclic conjugation.
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