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Title: Pyrazinacenes: aza analogues of acenes
Authors: Richards, Gary J.
Hill, Jonathan P.
Subbaiyan, Navaneetha K.
D'Souza, Francis
Karr, Paul A.
Elsegood, Mark R.J.
Teat, Simon J.
Mori, Toshiyuki
Ariga, Katsuhiko
Issue Date: 2009
Publisher: © American Chemical Society
Citation: RICHARDS, G.J. ... et al., 2009. Pyrazinacenes: aza analogues of acenes. Journal of Organic Chemistry, 74(23), pp.8914-8923.
Abstract: 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.
Description: This item is Closed Access.
Sponsor: 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.
Version: Closed access
DOI: 10.1021/jo901832n
URI: https://dspace.lboro.ac.uk/2134/15563
Publisher Link: http://dx.doi.org/10.1021/jo901832n
ISSN: 0022-3263
Appears in Collections:Closed Access (Chemistry)

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