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

Research output: Contribution to journalArticlepeer-review

49 Citations (Scopus)

Abstract

(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.

Original languageEnglish
Pages (from-to)8914-8923
Number of pages10
JournalJournal of Organic Chemistry
Volume74
Issue number23
DOIs
Publication statusPublished - 2009 Dec 4
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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