High-spin polyphenoxyls attached to star-shaped poly(phenylenevinylene)s

Hiroyuki Nishide, Makoto Miyasaka, Eishun Tsuchida

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36 Citations (Scopus)

Abstract

Star-shaped poly(1,2-phenylenevinylene)s 4-substituted with multiple pendant phenoxyls (2 and 3) were synthesized by polymerizing 2-bromo-4-(acetoxyphenyl)styrene in the presence of 1,3,5-triiodobenzene or 1,3,5-tris(3′,5′-diiodophenyl)benzene as the core via a simple one-pot Heck reaction and subsequent hydrolysis, phenolate formation, and heterogeneous oxidation. ESR spectra indicated a delocalized spin distribution into the core parts of the star-shaped molecules. The polyradicals, 2 and 3, were in a high-spin state at low temperature, and the ferromagnetic behavior was enhanced for the polyradical with a higher molecular weight. Although an average S of 3 remained at 3/2 to 4/2, the polyradical 2 even with a spin concentration of 0.8 spin/unit revealed an average S of 7/2 to 8/2. The 1,3,5-benzene core acted as an effective magnetic coupler to align the spins of the pendant phenoxyls through the star-shaped π-conjugated backbone.

Original languageEnglish
Pages (from-to)7399-7407
Number of pages9
JournalJournal of Organic Chemistry
Volume63
Issue number21
Publication statusPublished - 1998 Oct 16

ASJC Scopus subject areas

  • Organic Chemistry

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    Nishide, H., Miyasaka, M., & Tsuchida, E. (1998). High-spin polyphenoxyls attached to star-shaped poly(phenylenevinylene)s. Journal of Organic Chemistry, 63(21), 7399-7407.