1. Synthesis and Characterization of Planar Five-Ring-Fused Dithiophene-dione
- Author
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Xiao-Ping Cao, Huan Xu, Bin Li, Hao-Li Zhang, Jing Wang, and Wei-Jing Zeng
- Subjects
Chemistry ,Stereochemistry ,business.industry ,General Chemistry ,Ring (chemistry) ,Organic semiconductor ,Electronegativity ,Crystallography ,Planar ,Semiconductor ,Liquid crystal ,Polar effect ,business ,HOMO/LUMO - Abstract
A series of new organic semiconductors based on s-indaceno[1,2-b:5,6-b′]dithiophene-4,9-dione was successfully synthesized and characterized. The electron withdrawing carbonyl group lowers the LUMO energy levels, leading to increased electronegativities, which is beneficial for high photo-stability in air. The n-alkyl substituted compounds, 1c and 1d, crystallize with the rigid coplanar systems packed into slipped face-to-face π-stacks. Interestingly, 1c and 1d also show liquid crystalline behaviors, which give highly ordered molecular packing over large area.
- Published
- 2012
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