An annulene TCNQ derivative with rather weak acceptor properties

Reginald H. Mitchell, Xin Jin, Tetsuo Otsubo, Kazuo Takimiya

研究成果: Article査読

1 被引用数 (Scopus)

抄録

Reaction of the bridged [14]annulenequinone, trans-10b, 10c-dimethyl-10b, 10c-dihydropyrene-2,7-quinone (12), with malononitrile in the presence of pyridine and TiCl4 gave 68% of the deep-purple extended TCNQ derivative, α,α,α′,α′-tetracyano-trans-10b, 10c-dimethyl-10b, 10c-dihydropyrene-2,7-quinodimethide (13). In solution, quinodimethide 13 appears to form a complex with diethylamine, but is too weak an electron acceptor to form complexes with tetrathiafulvalene, TTF, and related donors. The reduction potential of 13 was substantially lower than that found for TCNQ itself, and in properties 13 behaves more like a benzannelated TCNQ derivative, e.g., α,α,α′,α′-tetracyanopentacene-7,14- quinodimethide (11), than a pyrene derivative, e.g., α,α,α′,α′-tetracyanopyrene-2,7- quinodimethide (6). This is in agreement with molecular orbital calculations, which indicate that the LUMOs of 13 and 11 are approximately 0.6 eV higher in energy than those for 6 and TCNQ.

本文言語English
ページ(範囲)611-615
ページ数5
ジャーナルCanadian Journal of Chemistry
75
6
DOI
出版ステータスPublished - 1997
外部発表はい

ASJC Scopus subject areas

  • 触媒
  • 化学 (全般)
  • 有機化学

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