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|Title: ||Pyrazinacenes: aza analogues of acenes|
|Authors: ||Richards, Gary J.|
Hill, Jonathan P.
Subbaiyan, Navaneetha K.
Karr, Paul A.
Elsegood, Mark R.J.
Teat, Simon J.
|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|
|Publisher Link: ||http://dx.doi.org/10.1021/jo901832n|
|Appears in Collections:||Closed Access (Chemistry)|
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