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Ring Reconstruction on a Trichalcogenasumanene Buckybowl: A Facile Approach to Donor–Acceptor‐Type [5‐6‐7] Fused Planar Polyheterocycles
Author(s) -
Li Xuexiang,
Zhu Yongtao,
Shao Jiafeng,
Chen Lichuan,
Zhao Sijie,
Wang Baolin,
Zhang Shangxi,
Shao Yongliang,
Zhang HaoLi,
Shao Xiangfeng
Publication year - 2015
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.201409620
Subject(s) - ring (chemistry) , acceptor , planar , photochemistry , chemistry , benzene , crystallography , transformation (genetics) , fluorescence , homo/lumo , ring strain , stereochemistry , materials science , molecule , organic chemistry , physics , optics , biochemistry , computer graphics (images) , computer science , gene , condensed matter physics
The transformation of trichalcogenasumanene buckybowls into donor–acceptor‐type [5‐6‐7] fused polyheterocycles is disclosed. The strategy involves a highly efficient ring‐opening of the flanking benzene upon oxidation at room temperature, and facile ring closure by functional‐group transformation. Crystallographic studies indicate that the resulting [5‐6‐7] fused polyheterocycles possess a planar conformation owing to the release of ring strain by expansion of one of the six‐membered flanking rings to the seven‐membered one. Additionally, the [5‐6‐7] fused polyheterocycles bear electron‐withdrawing groups, which reduce the HOMO–LUMO energy gap, and display broad absorption bands extending to λ =590 nm. Consequently, these compounds show strong red emission with fluorescence quantum yields of up to 38 %.