Poly(3-phenylgalvinoxylthiophene). A new conjugated polyradical with high spin concentration

Makoto Miyasaka, Tomoko Yamazaki, Hiroyuki Nishide

Research output: Contribution to journalArticle

13 Citations (Scopus)

Abstract

3-{4-[(3, 5-Di-tert-butyl-4-acetoxyphenyl)(3,5 -di-tert-butyl-4-oxocyclohexa-2,5-diene-1-ylidene)methyl]phenyl} thiophene (2a) was synthesized and oxidatively polymerized with ferric chloride at low temperature to yield poly(3-{4-[(3, 5-di-tert-butyl-4-acetoxyphenyl)(3,5-di-tert-butyl-4-oxocyclohexa-2,5 -diene-1-ylidene)-methyl]phenyl} thiophene) (1a). Head-to-tail content of 1a with a molecular weight of > 104 reached 92%. This polymer has a quinoid chromophore, and it reversibly showed a dark blue and red brownish color ascribed to an anion and a radical form, respectively. The polyradical 1 was almost quantitatively generated from 1b (a spin concentration of 0.9 spin/galvinoxyl unit), which was persistent at room temperature. The SQUID measurement at low temperature gave a spin quantum number (S) of 1/2 for 1, which indicated a paramagnetic ground state. 1 doped with iodine showed an electrical conductivity of 10-5 S cm-1. The polyradical derivatives, 7 and 8, displayed S of 1/2-2/2 and 1/2, respectively, and an electrical conductivity of 10-4-10-3 S cm-1 after doping.

Original languageEnglish
Pages (from-to)849-856
Number of pages8
JournalPolymer Journal
Volume33
Issue number11
Publication statusPublished - 2001

Keywords

  • π-Conjugated Polymer
  • Galvinoxyl
  • Magnetic Property
  • Oxidative Polymerization
  • Polyradical
  • Polythiophene

ASJC Scopus subject areas

  • Materials Chemistry
  • Polymers and Plastics

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