Electrochemical and ferromagnetic couplings in 4,4′,4″-(1,3,5-benzenetriyl)tris(phenoxyl) radical formation

Hiroyuki Nishide, R. Doi, Kenichi Oyaizu, E. Tsuchida

Research output: Contribution to journalArticle

21 Citations (Scopus)

Abstract

4,4′,4″-(1,3,5-Benzenetriyl)tris(2,6-di-tert-butylphenol) was prepared by the cross-coupling of 1,3,5-tribromobenzene and [4-(trimethylsiloxy)phenyl]magnesium bromide. X-ray analysis of the single crystal showed a propeller-like structure with a mean dihedral angle of 39° between the hydroxyphenyl and the core benzene. The phenoxyl mono-, di-, and triradicals were generated by the electrochemical oxidation of the trianion. A stepwise radical formation was revealed by a differential pulse voltammogram, electrolytic ESR spectroscopy, and a comproportionation reaction between the radicals, which was discussed as an effect of the π-conjugated but non-Kekulé-type coupler. The quartet and triplet ground state for the tri- and diradical, respectively, were confirmed by a SQUID measurement.

Original languageEnglish
Pages (from-to)1680-1685
Number of pages6
JournalJournal of Organic Chemistry
Volume66
Issue number5
DOIs
Publication statusPublished - 2001 Mar 9

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Electrochemical oxidation
SQUIDs
X ray analysis
Propellers
Dihedral angle
Benzene
Ground state
Paramagnetic resonance
Single crystals
Spectroscopy
magnesium bromide
2,6-di-tert-butylphenol
phenoxy radical
1,3,5-tribromobenzene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

Electrochemical and ferromagnetic couplings in 4,4′,4″-(1,3,5-benzenetriyl)tris(phenoxyl) radical formation. / Nishide, Hiroyuki; Doi, R.; Oyaizu, Kenichi; Tsuchida, E.

In: Journal of Organic Chemistry, Vol. 66, No. 5, 09.03.2001, p. 1680-1685.

Research output: Contribution to journalArticle

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abstract = "4,4′,4″-(1,3,5-Benzenetriyl)tris(2,6-di-tert-butylphenol) was prepared by the cross-coupling of 1,3,5-tribromobenzene and [4-(trimethylsiloxy)phenyl]magnesium bromide. X-ray analysis of the single crystal showed a propeller-like structure with a mean dihedral angle of 39° between the hydroxyphenyl and the core benzene. The phenoxyl mono-, di-, and triradicals were generated by the electrochemical oxidation of the trianion. A stepwise radical formation was revealed by a differential pulse voltammogram, electrolytic ESR spectroscopy, and a comproportionation reaction between the radicals, which was discussed as an effect of the π-conjugated but non-Kekul{\'e}-type coupler. The quartet and triplet ground state for the tri- and diradical, respectively, were confirmed by a SQUID measurement.",
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AU - Tsuchida, E.

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N2 - 4,4′,4″-(1,3,5-Benzenetriyl)tris(2,6-di-tert-butylphenol) was prepared by the cross-coupling of 1,3,5-tribromobenzene and [4-(trimethylsiloxy)phenyl]magnesium bromide. X-ray analysis of the single crystal showed a propeller-like structure with a mean dihedral angle of 39° between the hydroxyphenyl and the core benzene. The phenoxyl mono-, di-, and triradicals were generated by the electrochemical oxidation of the trianion. A stepwise radical formation was revealed by a differential pulse voltammogram, electrolytic ESR spectroscopy, and a comproportionation reaction between the radicals, which was discussed as an effect of the π-conjugated but non-Kekulé-type coupler. The quartet and triplet ground state for the tri- and diradical, respectively, were confirmed by a SQUID measurement.

AB - 4,4′,4″-(1,3,5-Benzenetriyl)tris(2,6-di-tert-butylphenol) was prepared by the cross-coupling of 1,3,5-tribromobenzene and [4-(trimethylsiloxy)phenyl]magnesium bromide. X-ray analysis of the single crystal showed a propeller-like structure with a mean dihedral angle of 39° between the hydroxyphenyl and the core benzene. The phenoxyl mono-, di-, and triradicals were generated by the electrochemical oxidation of the trianion. A stepwise radical formation was revealed by a differential pulse voltammogram, electrolytic ESR spectroscopy, and a comproportionation reaction between the radicals, which was discussed as an effect of the π-conjugated but non-Kekulé-type coupler. The quartet and triplet ground state for the tri- and diradical, respectively, were confirmed by a SQUID measurement.

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