Synthesis of dendritic, non-kekulé-, and nondisjoint-type triphenylmethanes terminated with galvinoxyl radicals

Eiji Fukuzaki, Naoki Takahashi, Shingo Imai, Hiroyuki Nishide, Andrzej Rajca

Research output: Contribution to journalArticle

15 Citations (Scopus)

Abstract

A series of triphenylmethanes terminated with (a) hydrogalvinoxyl(s), bis(4-tert-butylphenyl)-(4-hydrogalvinoxylphenyl)methoxymethane lad, tris(4-hydrogalvinoxylphenyl)methoxymethane 2ad, and tris{4-[bis(4- hydrogalvinoxylphenyl)methoxymethyl]phenyl}methoxymethane 3ad, were prepared and oxidized to the corresponding galvinoxyl radicals, 1af, 2af, and 3af, which have one, three, and six galvinoxyl radical(s), respectively. Chemical reduction of the galvinoxyl radicals with a Na/K alloy gave stable intermediates, i.e., the tetraanion, decaanion, and docosaanion. The tetraanion was oxidized with an equimolar amount of iodine at ca. 170 K to the galvinoxyl radical-combined triphenylmethyl radical 1cf. The ESR signal of the biradical at room temperature indicated an exchange interaction between the two radicals. The spectrum at 140 K had a zero-field splitting and ΔMs= ±2 transition signal at half-field, which are characteristic of a multiplet species.

Original languageEnglish
Pages (from-to)284-293
Number of pages10
JournalPolymer Journal
Volume37
Issue number4
DOIs
Publication statusPublished - 2005

Fingerprint

Exchange interactions
Iodine
Paramagnetic resonance
Temperature
triphenylmethane
galvinoxyl

Keywords

  • Dendrimer
  • Galvinoxyl Radical
  • High-spin Molecule
  • Non-Kekulé Structure
  • Triphenylmethane

ASJC Scopus subject areas

  • Polymers and Plastics
  • Materials Chemistry

Cite this

Synthesis of dendritic, non-kekulé-, and nondisjoint-type triphenylmethanes terminated with galvinoxyl radicals. / Fukuzaki, Eiji; Takahashi, Naoki; Imai, Shingo; Nishide, Hiroyuki; Rajca, Andrzej.

In: Polymer Journal, Vol. 37, No. 4, 2005, p. 284-293.

Research output: Contribution to journalArticle

Fukuzaki, Eiji ; Takahashi, Naoki ; Imai, Shingo ; Nishide, Hiroyuki ; Rajca, Andrzej. / Synthesis of dendritic, non-kekulé-, and nondisjoint-type triphenylmethanes terminated with galvinoxyl radicals. In: Polymer Journal. 2005 ; Vol. 37, No. 4. pp. 284-293.
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