Peripheral Hexabromination,Hexaphenylation, and Hexaethynylation of meso‐Aryl‐Substituted Subporphyrins |
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| Authors: | Eiji Tsurumaki Yasuhide Inokuma Shanmugam Easwaramoorthi Dr Jong Min Lim Dongho Kim Prof Dr Atsuhiro Osuka Prof Dr |
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| Institution: | 1. Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo‐ku, Kyoto 606‐8502 (Japan), Fax: (+81)?75‐753‐3970;2. Center for Ultrafast Optical Characteristics Control and Department of Chemistry, Yonsei University, Seoul 120‐749 (Korea), Fax: (+82)?2‐2123‐2434 |
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| Abstract: | Effective peripheral fabrication methods of meso‐aryl‐substituted subporphyrins were explored for the first time. Hexabrominated subporphyrins 2 were prepared quantitatively from the bromination of subporphyrins 1 with bromine. Hexaphenylated subporphyrins 3 and hexaethynylated subporphyrins 4 and 5 were synthesized by Suzuki–Miyaura coupling and Stille coupling, respectively, in good yields. X‐ray crystal structures of 2 b , 3 b , 4 b , and 5 a revealed preservation of the bowl‐shaped bent structures with bowl depths similar to that of 1 . Hexaethynylated subporphyrins exhibit large two‐photon‐absorption cross‐sections due to effective delocalization of the conjugated network to the ethynyl substituents. |
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| Keywords: | bromination cross‐coupling porphyrinoids structure elucidation subporphyrins |
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