Poly[(3,5-di-tert-butyl-4-hydroxyphenyl)acetylene] and its polyradical derivative

Hiroyuki Nishide, Naoki Yoshioka, Katsunari Inagaki, Takahiko Kaku, Eishun Tsuchida

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Abstract

(3,5-Di-tert-butyl-4-hydroxyphenyl)acetylene (8) was synthesized and polymerized with WCIs and MoCl5, giving a novel and solvent-soluble conjugated polymer, poly[(3,5-di-tert-butyl-4-hydroxyphenyl)acetylene] (3). Visible absorption of the polymer indicated a fairly long π-conjugated system along the main chain. The polymer yielded its polyanion 10 and polyradical derivative 4 after the treatment of its solution with an alkali and oxidizing reagent, respectively. The polyradical 4 was surprisingly stable, and spin concentration was increased up to 2.3 × 1023 spins/molar (hydroxyphenyl)acetylene residue. ESR spectra of the polyradical 4 in solution suggested that the formed upaired electrons were delocalized along the polyacetylene main chain. 4 was also very stable even in solid state. Spin-exchange interaction observed in 4 strongly depended on its spin concentration. Antiferromagnetic interaction between the upaired electrons was suggested from the temperature dependency of the ESR signal intensity.

Original languageEnglish
Pages (from-to)569-575
Number of pages7
JournalMacromolecules
Volume25
Issue number2
Publication statusPublished - 1992 Jan 1

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Acetylene
Derivatives
Paramagnetic resonance
Polymers
Polyacetylenes
Electrons
Exchange interactions
Conjugated polymers
Alkalies
3,5-di-tert-butyl-4-hydroxyphenyl
Temperature

ASJC Scopus subject areas

  • Materials Chemistry

Cite this

Nishide, H., Yoshioka, N., Inagaki, K., Kaku, T., & Tsuchida, E. (1992). Poly[(3,5-di-tert-butyl-4-hydroxyphenyl)acetylene] and its polyradical derivative. Macromolecules, 25(2), 569-575.

Poly[(3,5-di-tert-butyl-4-hydroxyphenyl)acetylene] and its polyradical derivative. / Nishide, Hiroyuki; Yoshioka, Naoki; Inagaki, Katsunari; Kaku, Takahiko; Tsuchida, Eishun.

In: Macromolecules, Vol. 25, No. 2, 01.01.1992, p. 569-575.

Research output: Contribution to journalArticle

Nishide, H, Yoshioka, N, Inagaki, K, Kaku, T & Tsuchida, E 1992, 'Poly[(3,5-di-tert-butyl-4-hydroxyphenyl)acetylene] and its polyradical derivative', Macromolecules, vol. 25, no. 2, pp. 569-575.
Nishide H, Yoshioka N, Inagaki K, Kaku T, Tsuchida E. Poly[(3,5-di-tert-butyl-4-hydroxyphenyl)acetylene] and its polyradical derivative. Macromolecules. 1992 Jan 1;25(2):569-575.
Nishide, Hiroyuki ; Yoshioka, Naoki ; Inagaki, Katsunari ; Kaku, Takahiko ; Tsuchida, Eishun. / Poly[(3,5-di-tert-butyl-4-hydroxyphenyl)acetylene] and its polyradical derivative. In: Macromolecules. 1992 ; Vol. 25, No. 2. pp. 569-575.
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N2 - (3,5-Di-tert-butyl-4-hydroxyphenyl)acetylene (8) was synthesized and polymerized with WCIs and MoCl5, giving a novel and solvent-soluble conjugated polymer, poly[(3,5-di-tert-butyl-4-hydroxyphenyl)acetylene] (3). Visible absorption of the polymer indicated a fairly long π-conjugated system along the main chain. The polymer yielded its polyanion 10 and polyradical derivative 4 after the treatment of its solution with an alkali and oxidizing reagent, respectively. The polyradical 4 was surprisingly stable, and spin concentration was increased up to 2.3 × 1023 spins/molar (hydroxyphenyl)acetylene residue. ESR spectra of the polyradical 4 in solution suggested that the formed upaired electrons were delocalized along the polyacetylene main chain. 4 was also very stable even in solid state. Spin-exchange interaction observed in 4 strongly depended on its spin concentration. Antiferromagnetic interaction between the upaired electrons was suggested from the temperature dependency of the ESR signal intensity.

AB - (3,5-Di-tert-butyl-4-hydroxyphenyl)acetylene (8) was synthesized and polymerized with WCIs and MoCl5, giving a novel and solvent-soluble conjugated polymer, poly[(3,5-di-tert-butyl-4-hydroxyphenyl)acetylene] (3). Visible absorption of the polymer indicated a fairly long π-conjugated system along the main chain. The polymer yielded its polyanion 10 and polyradical derivative 4 after the treatment of its solution with an alkali and oxidizing reagent, respectively. The polyradical 4 was surprisingly stable, and spin concentration was increased up to 2.3 × 1023 spins/molar (hydroxyphenyl)acetylene residue. ESR spectra of the polyradical 4 in solution suggested that the formed upaired electrons were delocalized along the polyacetylene main chain. 4 was also very stable even in solid state. Spin-exchange interaction observed in 4 strongly depended on its spin concentration. Antiferromagnetic interaction between the upaired electrons was suggested from the temperature dependency of the ESR signal intensity.

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