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Trichalcogenasumanene ortho ‐Quinones: Synthesis, Properties, and Transformation into Various Heteropolycycles
Author(s) -
Sun Yantao,
Li Xuexiang,
Sun Chunlin,
Shen Hongguang,
Hou Xueqing,
Lin Dongxu,
Zhang HaoLi,
Di Chongan,
Zhu Daoben,
Shao Xiangfeng
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201707397
Subject(s) - regioselectivity , planar , solid state , chemistry , absorbance , crystallography , transformation (genetics) , stereochemistry , materials science , organic chemistry , catalysis , computer graphics (images) , chromatography , computer science , biochemistry , gene
The regioselective transformation of heterobuckybowl trichalcogenasumanenes 1 a , b at peripheral butoxy groups afforded trichalcogenasumanene ortho ‐quinones 2 a , b . Compounds 2 a , b are distinct from 1 a , b in terms of their molecular geometry and electronic state; that is, they have a shallower bowl depth and show absorbance in the NIR region. The reaction of 2 a , b with diamines resulted in a variety of heteropolycycles, including molecular spoon 3 a – 6 a , planar π‐systems 3 b – 6 b , and highly twisted [7‐6‐6]‐fused systems 7 a , b . These new heteropolycycles had different optical/electrical properties: 4 a,b showed hole mobility of approximately 0.002 cm 2 V −1 s −1 , 6 a displayed red emission in both solution and the solid state, and 7 a , b formed tight stacks of the curved π‐surface.