Poly(3-phenylgalvinoxylthiophene). A New Conjugated Polyradical with High Spin Concentration.

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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.

Journal

  • Polymer Journal

    Polymer Journal 33 (11), 849-856, 2001

    The Society of Polymer Science, Japan

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