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

H. Nishide, R. Doi, K. 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

ASJC Scopus subject areas

  • Organic Chemistry

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