N,N-bis(4-{5-[N,N-bis(4-methoxyphenyl)-N-yloammonio]-2-methylstyryl}phenyl) ammoniumyl triradical: A trimer model of high-spin poly[(4-methoxyphenyl-N- yloammonio)-1,2(or 4)-phenylenevinylene-1,2(or 4)-phenylene]

Eiji Fukuzaki, Shigemoto Abe, Hiroyuki Nishide

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Hyperbranched poly[(4-methoxyphenyl-N-yloammonio)-1,2(or 4)-phenylenevinylene-1,2(or 4)-phenylene], obtained by the polycondensation of N-(4-methoxyphenyl)-N-(4-vinylphenyl)-3-bromo-4-vinylaniline and the subsequent oxidation, three-directionally satisfied the non-Kekulé-type π-conjugation and ferromagnetic connectivity of the unpaired electrons of triarylammoniumyl cationic radicals, and behaved as a high-spin organic polymer even at room temperature. The trimer model compound, N-(4-{5-[N,N-bis(4- methoxyphenyl)amino]-2-methylstyryl}-3-methylphenyl)-N-(4-{5-[N, N-bis(4-methoxyphenyl)amino]-2-methylstyryl}phenyl)-4-methoxyaniline, was synthesized from N-(4-methoxyphenyl)-N-(4-vinylphenyl)-3-methyl-4-vinylaniline. The corresponding ammoniumyl triradical displayed an average S (spin quantum number) value of 3/2, which supported the strong spin-coupling between the unpaired electrons of the ammoniumyl radicals through the π-conjugated and branched phenylenevinylene structure. Head-to-tail linkage and the branched structure of the polymer were also studied by a model reaction of N-(4-methoxyphenyl)-N-(4-vinylphenyl)-3-methyl-4-vinylaniline and bromobenzene.

Original languageEnglish
Pages (from-to)953-958
Number of pages6
JournalBulletin of the Chemical Society of Japan
Issue number6
Publication statusPublished - 2006


ASJC Scopus subject areas

  • Chemistry(all)

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