Poly(1,2-phenylenevinylene)s bearing nitronyl nitroxide and galvinoxyl at the 4-position

π-Conjugated and non-Kekulé-type polyradicals with a triplet ground state

Hiroyuki Nishide, Yasuhiro Hozumi, Takeshi Nii, Eishun Tsuchida

Research output: Contribution to journalArticle

25 Citations (Scopus)

Abstract

Poly[4-(4′,4′,5′,5′-tetramethyl-3′-oxido- 1′-oxylimidazolinium-2′-yl)-1,2-phenylenevinylene] (1) and poly[4-[(3,5-di-tert-butyl-4-oxyphenyl)(3,5-di-tert-butyl-4-oxocyclohexa-2,5- diene-1-ylidene)methyl]-1,2-phenylenevinylene] (2) were synthesized via the polymerization of 2-bromo-4-[1′,3′-bis(tert-butyldimethylsiloxy)-4′,4′, 5′,5′-tetramethylimidazolin-2′-yl]styrene (10) and 2-iodo-4-[(3,5-di-tert-butyl-4-acetoxyphenyl)(3,5-di-tert-butyl-4-oxocyclohexa- 2,5-dien-1-ylidene)methyl]styrene (12), respectively, using a palladium catalyst. Their spin (radical) concentration could be increased beyond 0.9 per molar monomer unit, and they were stable even in air at room temperature. The polyradicals satisfied an alternant but non-Kekulé-type π-conjugated structure and displayed a triplet ground state or an intramacromolecular ferromagnetic spin coupling in the SQUID magnetization measurement.

Original languageEnglish
Pages (from-to)3986-3991
Number of pages6
JournalMacromolecules
Volume30
Issue number14
Publication statusPublished - 1997 Jul 14

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Bearings (structural)
Styrene
Ground state
SQUIDs
Palladium
Magnetization
Monomers
Polymerization
Catalysts
Air
Temperature
galvinoxyl

ASJC Scopus subject areas

  • Materials Chemistry

Cite this

Poly(1,2-phenylenevinylene)s bearing nitronyl nitroxide and galvinoxyl at the 4-position : π-Conjugated and non-Kekulé-type polyradicals with a triplet ground state. / Nishide, Hiroyuki; Hozumi, Yasuhiro; Nii, Takeshi; Tsuchida, Eishun.

In: Macromolecules, Vol. 30, No. 14, 14.07.1997, p. 3986-3991.

Research output: Contribution to journalArticle

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abstract = "Poly[4-(4′,4′,5′,5′-tetramethyl-3′-oxido- 1′-oxylimidazolinium-2′-yl)-1,2-phenylenevinylene] (1) and poly[4-[(3,5-di-tert-butyl-4-oxyphenyl)(3,5-di-tert-butyl-4-oxocyclohexa-2,5- diene-1-ylidene)methyl]-1,2-phenylenevinylene] (2) were synthesized via the polymerization of 2-bromo-4-[1′,3′-bis(tert-butyldimethylsiloxy)-4′,4′, 5′,5′-tetramethylimidazolin-2′-yl]styrene (10) and 2-iodo-4-[(3,5-di-tert-butyl-4-acetoxyphenyl)(3,5-di-tert-butyl-4-oxocyclohexa- 2,5-dien-1-ylidene)methyl]styrene (12), respectively, using a palladium catalyst. Their spin (radical) concentration could be increased beyond 0.9 per molar monomer unit, and they were stable even in air at room temperature. The polyradicals satisfied an alternant but non-Kekul{\'e}-type π-conjugated structure and displayed a triplet ground state or an intramacromolecular ferromagnetic spin coupling in the SQUID magnetization measurement.",
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