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Formation and Isolation of a Four‐Electron‐Reduced Porphyrin Derivative by Reduction of a Stable 20π Isophlorin
Authors:Wataru Suzuki  Dr. Hiroaki Kotani  Dr. Tomoya Ishizuka  Prof. Dr. Yoshihito Shiota  Prof. Dr. Kazunari Yoshizawa  Prof. Dr. Takahiko Kojima
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
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.
Keywords:electrochemistry  electron transfer  isophlorins  porphyrins  redox chemistry
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