Spontaneous Formation of an Air-Stable Radical upon the Direct Fusion of Diphenylmethane to a Triarylporphyrin

Kenichi Kato, Wonhee Cha, Juwon Oh, Ko Furukawa, Hideki Yorimitsu, Dongho Kim, Atsuhiro Osuka

Research output: Contribution to journalArticle

30 Citations (Scopus)

Abstract

The direct fusion of a diphenylmethane segment to a NiII5,10,15-triarylporphyrin with three linkages furnished an air- and moisture-stable neutral radical through unexpected and spontaneous oxidation. This radical was demetalated by treatment with H2SO4and CF3CO2H to provide the corresponding free-base radical. These porphyrin radicals are very stable owing to spin delocalization and have been fully characterized through UV/Vis/NIR absorption spectroscopy, X-ray crystallographic analysis, magnetic susceptibility measurements, electrochemical studies, laser-based ultrafast spectroscopic studies, and theoretical calculations. They were chemically oxidized and reduced to the corresponding cation and anion but did not react with hydrogen-atom donors.

Original languageEnglish
Pages (from-to)8711-8714
Number of pages4
JournalAngewandte Chemie - International Edition
Volume55
Issue number30
DOIs
Publication statusPublished - 2016 Jul 18

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X ray absorption spectroscopy
Porphyrins
Magnetic susceptibility
Anions
Cations
Hydrogen
Moisture
Negative ions
Fusion reactions
Positive ions
Atoms
Oxidation
Lasers
Air
diphenylmethane

All Science Journal Classification (ASJC) codes

  • Catalysis
  • Chemistry(all)

Cite this

Kato, Kenichi ; Cha, Wonhee ; Oh, Juwon ; Furukawa, Ko ; Yorimitsu, Hideki ; Kim, Dongho ; Osuka, Atsuhiro. / Spontaneous Formation of an Air-Stable Radical upon the Direct Fusion of Diphenylmethane to a Triarylporphyrin. In: Angewandte Chemie - International Edition. 2016 ; Vol. 55, No. 30. pp. 8711-8714.
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Spontaneous Formation of an Air-Stable Radical upon the Direct Fusion of Diphenylmethane to a Triarylporphyrin. / Kato, Kenichi; Cha, Wonhee; Oh, Juwon; Furukawa, Ko; Yorimitsu, Hideki; Kim, Dongho; Osuka, Atsuhiro.

In: Angewandte Chemie - International Edition, Vol. 55, No. 30, 18.07.2016, p. 8711-8714.

Research output: Contribution to journalArticle

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AB - The direct fusion of a diphenylmethane segment to a NiII5,10,15-triarylporphyrin with three linkages furnished an air- and moisture-stable neutral radical through unexpected and spontaneous oxidation. This radical was demetalated by treatment with H2SO4and CF3CO2H to provide the corresponding free-base radical. These porphyrin radicals are very stable owing to spin delocalization and have been fully characterized through UV/Vis/NIR absorption spectroscopy, X-ray crystallographic analysis, magnetic susceptibility measurements, electrochemical studies, laser-based ultrafast spectroscopic studies, and theoretical calculations. They were chemically oxidized and reduced to the corresponding cation and anion but did not react with hydrogen-atom donors.

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