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Pyrazinacenes: aza analogues of acenes
journal contribution
posted on 2014-08-15, 10:28 authored by Gary J. Richards, Jonathan P. Hill, Navaneetha K. Subbaiyan, Francis D'Souza, Paul A. Karr, Mark ElsegoodMark Elsegood, Simon J. Teat, Toshiyuki Mori, Katsuhiko ArigaA 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 CHEMISTRYVolume
74Issue
23Pages
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 SocietyVersion
- NA (Not Applicable or Unknown)
Publication date
2009Notes
This item is Closed Access.ISSN
0022-3263Publisher version
Language
- en