Formation and Isolation of a Four‐Electron‐Reduced Porphyrin Derivative by Reduction of a Stable 20π Isophlorin |
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Authors: | Wataru Suzuki Dr. Hiroaki Kotani Dr. Tomoya Ishizuka Prof. Dr. Yoshihito Shiota Prof. Dr. Kazunari Yoshizawa Prof. Dr. Takahiko Kojima |
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Affiliation: | 1. Department of Chemistry, Graduate School of Pure and Applied Sciences, University of Tsukuba, Ibaraki, Japan;2. Institute for Materials Chemistry and Engineering, Kyushu University, Nishi-Ku, Fukuoka, Japan |
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Abstract: | The two‐electron reduction of a diprotonated dodecaphenylporphyrin derivative by Na2S2O4 gave a corresponding isophlorin ( Iph ) selectively. Formation of Iph was confirmed by spectroscopic measurements and the isolation of tetramethylated Iph . Further reduction of Iph proceeded to form an unprecedented four‐electron‐reduced porphyrin ( IphH2 ), which was fully characterized by spectroscopic and X‐ray crystallographic analysis. IphH2 , with a unique conformation, could be oxidized to reproduce the starting porphyrin, resulting in a proton‐coupled four‐electron reversible redox system. |
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Keywords: | electrochemistry electron transfer isophlorins porphyrins redox chemistry |
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