High-spin polyphenoxyl based on poly(1,4-phenyleneethynylene)

Hiroyuki Nishide, Tadatoshi Maeda, Kenichi Oyaizu, Eishun Tsuchida

Research output: Contribution to journalArticle

33 Citations (Scopus)

Abstract

Rodlike poly(1,4-phenyleneethynylene) 2-substituted with multiple pendant phenoxyls 1 was synthesized by polymerizing 4-bromo-2-(3,5-di-tert- butyl-4-hydroxyphenyl)ethynylbenzene 10a using the catalyst of a palladium- triphenylphosphine complex and cuprous iodide and subsequent heterogeneous oxidation. The corresponding dimer 2 was also synthesized; X-ray analysis of its precursor 4 indicated a linear phenyleneethynylene backbone and twisted dihedral angles of 50 and 77°for the pendant phenol groups. ESR spectra suggested a delocalized spin distribution from the pendant phenoxyl to the backbone. The diphenoxyl 2 had a triplet (S = 2/2) ground state. The spin concentration of the polyphenoxyl 1 could not be increased beyond 0.7 spin/unit due to its low solvent solubility; 1 with a spin concentration of 0.62 had an average S of 3/2.

Original languageEnglish
Pages (from-to)7129-7134
Number of pages6
JournalJournal of Organic Chemistry
Volume64
Issue number19
DOIs
Publication statusPublished - 1999 Sep 17

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X ray analysis
Palladium
Dihedral angle
Phenol
Dimers
Ground state
Paramagnetic resonance
Solubility
Oxidation
Catalysts
phenyleneethynylene
triphenylphosphine
3,5-di-tert-butyl-4-hydroxyphenyl
cuprous iodide
phenylacetylene

ASJC Scopus subject areas

  • Organic Chemistry

Cite this

High-spin polyphenoxyl based on poly(1,4-phenyleneethynylene). / Nishide, Hiroyuki; Maeda, Tadatoshi; Oyaizu, Kenichi; Tsuchida, Eishun.

In: Journal of Organic Chemistry, Vol. 64, No. 19, 17.09.1999, p. 7129-7134.

Research output: Contribution to journalArticle

Nishide, Hiroyuki ; Maeda, Tadatoshi ; Oyaizu, Kenichi ; Tsuchida, Eishun. / High-spin polyphenoxyl based on poly(1,4-phenyleneethynylene). In: Journal of Organic Chemistry. 1999 ; Vol. 64, No. 19. pp. 7129-7134.
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