Pyrazine-containing acene-type molecular ribbons with up to 16 rectilinearly arranged fused aromatic rings

被引:179
作者
Gao, Baoxiang [1 ,2 ]
Wang, Ming [1 ]
Cheng, Yanxiang [1 ]
Wang, Lixiang [1 ]
Jing, Xiabin [1 ]
Wang, Fosong [1 ]
机构
[1] Chinese Acad Sci, Changchun Inst Appl Chem, State Key Lab Polymer Phys & Chem, Changchun 130022, Peoples R China
[2] Hebei Univ, Coll Chem & Environm Sci, Baoding 071002, Peoples R China
关键词
D O I
10.1021/ja800311a
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
A series of acene-type conjugated molecules(1-5) containing 2-6 pyrazine units and up to 16 rectilinearly arranged fused aromatic rings were synthesized by condensation coupling of 1,2-diamines and 1,2-diketones. The energy gap of the molecules estimated from absorption edge decreases with an increase in molecular length, indicating the well-delocalized nature of the molecules. The cyclic voltarnmetry measurements suggest that the n-type properties of these ribbonlike pyrazine derivatives are dependent on the molecular length and the number of the pyrazine units. As the number of pyrazine units and the molecular length increase, the first reduction wave onset is shifted from -1.16 to -0.62 V (vs Ag/AgCl), corresponding to the LUMO energy levels of -3.24 and -3.78 eV, respectively. These molecules tend to aggregate in solution more readily with an increase in molecular length, as evident by H-1 NMR and LIV-vis absorption spectra. Introduction of t-butyl groups in pyrene units can noticeably suppress the aggregation of these molecules in solution. High electron affinity, high environmental stability, and ease of structural modification make these compounds excellent candidates as a new class of n-type semiconductors.
引用
收藏
页码:8297 / 8306
页数:10
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