Pyrazinacenes: Aza Analogues of Acenes
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- 作者：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
- 刊名：Journal of Organic Chemistry
- 出版年：2009
- 出版时间：December 4, 2009
- 年：2009
- 卷：74
- 期：23
- 页码：8914-8923
- 全文大小：1179K
- 年卷期：v.74,no.23(December 4, 2009)
- ISSN：1520-6904
文摘
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.