Poly(1,2-phenylenevinylene) ferromagnetically 3,5-bearing phenoxyl radicals

Hiroyuki Nishide, Makoto Miyasaka, Ryuji Doi, Takashi Araki

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

A π-conjugated but non-Kekulé- and nondisjoint-type molecule, poly(1,2-phenylenevinylene) 3,5-disubstituted with pendant phenoxyl radicals (1a), was designed as a new high-spin organic polymer and synthesized by the head-to-tail coupling polymerization of 2-bromo-3,5-bis(3,5-di-tert-butyl-4-aceotoxyphenyl)styrene (3) using a palladium catalyst. The corresponding high-spin dimer model compound bearing four phenoxyl radicals (2a) was also synthesized. The stepwise radical formation in 1 and 2 was electrochemically studied. The ESR signal at ΔMs = ±2 indicated a triplet ground state for 1 and 2. However, the SQUID data revealed that the spin concentration and the average spin quantum number of 1a and 2a remained at ca. 0.5 spin/phenol unit and 2/2, respectively. A degradation at the vinylene bridge was suggested after the radical generation.

Original languageEnglish
Pages (from-to)690-698
Number of pages9
JournalMacromolecules
Volume35
Issue number3
DOIs
Publication statusPublished - 2002 Jan 29

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Bearings (structural)
Organic polymers
SQUIDs
Dimers
Ground state
Palladium
Phenols
Paramagnetic resonance
Styrene
Polymerization
Degradation
Catalysts
Molecules
Phenol
phenoxy radical

ASJC Scopus subject areas

  • Materials Chemistry

Cite this

Poly(1,2-phenylenevinylene) ferromagnetically 3,5-bearing phenoxyl radicals. / Nishide, Hiroyuki; Miyasaka, Makoto; Doi, Ryuji; Araki, Takashi.

In: Macromolecules, Vol. 35, No. 3, 29.01.2002, p. 690-698.

Research output: Contribution to journalArticle

Nishide, Hiroyuki ; Miyasaka, Makoto ; Doi, Ryuji ; Araki, Takashi. / Poly(1,2-phenylenevinylene) ferromagnetically 3,5-bearing phenoxyl radicals. In: Macromolecules. 2002 ; Vol. 35, No. 3. pp. 690-698.
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