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

Wataru Suzuki, Hiroaki Kotani, Tomoya Ishizuka, Yoshihito Shiota, Kazunari Yoshizawa, Takahiko Kojima

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4 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1973-1977
Number of pages5
JournalAngewandte Chemie - International Edition
Volume57
Issue number7
DOIs
Publication statusPublished - Feb 12 2018

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Porphyrins
Derivatives
Electrons
Conformations
Protons
X rays

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Formation and Isolation of a Four-Electron-Reduced Porphyrin Derivative by Reduction of a Stable 20π Isophlorin. / Suzuki, Wataru; Kotani, Hiroaki; Ishizuka, Tomoya; Shiota, Yoshihito; Yoshizawa, Kazunari; Kojima, Takahiko.

In: Angewandte Chemie - International Edition, Vol. 57, No. 7, 12.02.2018, p. 1973-1977.

Research output: Contribution to journalArticle

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