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Pyrazinacenes: aza analogues of acenes

journal contribution
posted on 15.08.2014, 10:28 by Gary J. Richards, Jonathan P. Hill, Navaneetha K. Subbaiyan, Francis D'Souza, Paul A. Karr, Mark Elsegood, Simon J. Teat, Toshiyuki Mori, Katsuhiko Ariga
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 derWaals 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.

Funding

This research was supported by the World Premier International Research Center Initiative (WPI Initiative) on Materials Nanoarchitectonics, by Grant-in-Aid for Scientific Research on Priority Area “Super-Hierarchical Structures” from Ministry of Education, Culture, Sports, Science and Technology, Japan, the National Science Foundation (Grant 0804015 to F.D.) and NSF-EPSCoR programs.

History

School

  • Science

Department

  • Chemistry

Published in

JOURNAL OF ORGANIC CHEMISTRY

Volume

74

Issue

23

Pages

8914 - 8923 (10)

Citation

RICHARDS, G.J. ... et al., 2009. Pyrazinacenes: aza analogues of acenes. Journal of Organic Chemistry, 74(23), pp.8914-8923.

Publisher

© American Chemical Society

Version

NA (Not Applicable or Unknown)

Publication date

2009

Notes

This item is Closed Access.

ISSN

0022-3263

Language

en

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Keywords

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