- Extension of N-Heteroacenes through a Four-Membered Ring
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The synthesis of novel π-extended N-heteroacenes, which have a large tetraazaacene subunit and a quinoxaline subunit connected through a four-membered ring, is reported. They were studied with experimental and computational methods in comparison to the corresponding tetraazaacenes. As found from the DFT calculation, the four-membered ring is a better linker than a five-membered ring or a C-C single bond to extend N-heteroacenes for a new design of n-type semiconductors in terms of the spatial delocalization and energy level of LUMO as well as the reorganization energy. In solution-processed thin film transistors, the π-extended N-heteroacenes are found to function as n-type semiconductors with field effect mobility of up to 0.02?cm2 V-1 s-1 under ambient conditions. Gang of four: This study demonstrates that N-heteroacenes can be extended through a four-membered ring into linear polycyclic frameworks with up to eight fused rings. It was found that the four-membered ring is a useful linker to extend electron delocalization for n-type organic semiconductors.
- Yang, Shuaijun,Shan, Bowen,Xu, Xiaomin,Miao, Qian
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supporting information
p. 6637 - 6642
(2016/05/09)
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- Molecular packing and n-channel thin film transistors of chlorinated cyclobuta[1,2-b:3,4-b′]diquinoxalines
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Novel chlorinated cyclobuta[1,2-b:3,4-b′]diquinoxalines were synthesized and investigated in the solid state. It is found that their molecular packing can be tuned by varying the number and position of chlorine substituents, and 2,8-dichloro-cyclobuta[1,2-b:3,4-b′]diquinoxaline either in pure form or as a mixture with its regioisomer functions as n-type semiconductors in organic thin film transistors with a field effect mobility of up to 0.42 cm2 V-1 s-1 and 0.20 cm2 V-1 s-1, respectively. This journal is
- Yang, Shuaijun,Liu, Danqing,Xu, Xiaomin,Miao, Qian
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supporting information
p. 4275 - 4278
(2015/03/18)
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- BIPHENYLENES AND HETEROCYCLIC ANALOGUES OF BIPHENYLENE. PART III. PREPARATION OF PYRAZINE AND QUINOXALINE ANALOGUES OF BIPHENYLENE BY NITROGEN EXTRUSION.
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Flash vacuum pyrolysis of pyrazinocinnolines (8), obtained by condensing 3,4-diaminocinnoline with α-dicarbonyl compounds, gives 1,4-diazabiphenylenes.Condensation of 3,4-dibromocinnoline with o-phenylenediamine, and oxidation of the isolable dihydrointer
- Kanoktanaporn, Santhi,MacBride, J. A. Hugh
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p. 2941 - 2949
(2007/10/02)
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