Stable [48]‐, [50]‐, and [52]Dodecaphyrins(1.1.0.1.1.0.1.1.0.1.1.0): The Largest Hückel Aromatic Molecules |
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| Authors: | Takanori Soya Woojae Kim Prof?Dr Dongho Kim Prof?Dr Atsuhiro Osuka |
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| Institution: | 1. Department of Chemistry, Graduate School of Science, Kyoto University, Sakyo‐ku, Kyoto, 606‐8502 (Japan);2. Spectroscopy Laboratory for Functional π‐Electronic Systems and Department of Chemistry, Yonsei University, Seoul 120‐749 (Korea) |
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| Abstract: | 52]Dodecaphyrin(1.1.0.1.1.0.1.1.0.1.1.0) was quantitatively oxidized with 2,3‐dichloro‐5,6‐dicyano‐1,4‐benzoquinone (DDQ) to the corresponding 50]dodecaphyrin. Further oxidation of 50]dodecaphyrin with MnO2 quantitatively afforded 48]dodecaphyrin. Of the three, 50]dodecaphyrin showed Hückel aromatic character as the largest aromatic molecule reported to date. Protonation of 50]dodecaphyrin with methanesulfonic acid (MSA) led to the formation of a planar tetraprotonated species that displayed a sharp and intense Soret‐like band at 906 nm with ε=6.5×105 M ?1 cm?1 and Q‐band‐like bands at 1346 and 1600 nm. |
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| Keywords: | aromaticity dodecaphyrins expanded porphyrins planar molecules protonation |
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