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Formation and Isolation of a Four‐Electron‐Reduced Porphyrin Derivative by Reduction of a Stable 20π Isophlorin
Author(s) -
Suzuki Wataru,
Kotani Hiroaki,
Ishizuka Tomoya,
Shiota Yoshihito,
Yoshizawa Kazunari,
Kojima Takahiko
Publication year - 2018
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201711058
Subject(s) - porphyrin , redox , derivative (finance) , chemistry , reduction (mathematics) , electron , one electron reduction , photochemistry , crystallography , inorganic chemistry , electrochemistry , physics , mathematics , geometry , electrode , quantum mechanics , financial economics , economics
The two‐electron reduction of a diprotonated dodecaphenylporphyrin derivative by Na 2 S 2 O 4 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 ( IphH 2 ), which was fully characterized by spectroscopic and X‐ray crystallographic analysis. IphH 2 , with a unique conformation, could be oxidized to reproduce the starting porphyrin, resulting in a proton‐coupled four‐electron reversible redox system.