Formation and Isolation of a Four‐Electron‐Reduced Porphyrin Derivative by Reduction of a Stable 20π Isophlorin | Zendy

Suzuki Wataru | Zendy; Kotani Hiroaki | Zendy; Ishizuka Tomoya | Zendy; Shiota Yoshihito | Zendy; Yoshizawa Kazunari | Zendy; Kojima Takahiko | Zendy

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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

Language(s) - English

Resource type - Journals

eISSN - 1521-3757

pISSN - 0044-8249

DOI - 10.1002/ange.201711058

Subject(s) - porphyrin , chemistry , derivative (finance) , redox , one electron reduction , reduction (mathematics) , electron , photochemistry , crystallography , inorganic chemistry , electrochemistry , economics , physics , geometry , mathematics , electrode , quantum mechanics , financial 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.

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