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Synthesis and Characterization of Planar Five‐Ring‐Fused Dithiophene‐dione
Author(s) -
Wang Jing,
Zeng Weijing,
Xu Huan,
Li Bin,
Cao Xiaoping,
Zhang Haoli
Publication year - 2012
Publication title -
chinese journal of chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.28
H-Index - 41
eISSN - 1614-7065
pISSN - 1001-604X
DOI - 10.1002/cjoc.201100141
Subject(s) - electronegativity , chemistry , homo/lumo , alkyl , ring (chemistry) , planar , polar effect , crystallography , characterization (materials science) , semiconductor , stereochemistry , nanotechnology , organic chemistry , molecule , optoelectronics , materials science , computer graphics (images) , physics , computer science
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.