Pyrazinacenes: Aza analogues of acenes

Gary J. Richards, Jonathan P. Hill, Navaneetha K. Subbaiyan, Francis D'Souza, Paul A. Karr, Mark R.J. Elsegood, Simon J. Teat, Toshiyuki Mori, Katsuhiko Ariga

研究成果: Article査読

51 被引用数 (Scopus)

抄録

(Chemical Equation Presented) A series of edge-sharing condensed oligopyrazine analogues of acenes, the pyrazinacenes, were synthesized and characterized. X-ray crystallographic determinations revealed intermolecular interactions that affect the propensity of the molecules to undergo π-π stacking. Increasing heteroatom substitution of the acene framework induces shorter intermolecular π-π stacking distances (shorter than for graphite) probably due to lower van der Waals radius of nitrogen atoms. Hydrogen bonding is also a determining factor in the case of compounds containing reduced pyrazine rings. Combined electrochemical, electronic absorption, and computational investigations indicate the substantial electron deficiency of the compounds composed of fused pyrazine rings. The pyrazinacenes are expected to be good candidates as materials for organic thin film transistors.

本文言語English
ページ(範囲)8914-8923
ページ数10
ジャーナルJournal of Organic Chemistry
74
23
DOI
出版ステータスPublished - 2009 12 4
外部発表はい

ASJC Scopus subject areas

  • 有機化学

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