Ring Reconstruction on a Trichalcogenasumanene Buckybowl: A Facile Approach to Donor–Acceptor‐Type [5‐6‐7] Fused Planar Polyheterocycles

Autor: Sijie Zhao, Baolin Wang, Hao-Li Zhang, Xuexiang Li, Shangxi Zhang, Yongtao Zhu, Yongliang Shao, Li-Chuan Chen, Jiafeng Shao, Xiangfeng Shao
Rok vydání: 2014
Předmět:
Zdroj: Angewandte Chemie International Edition. 54:267-271
ISSN: 1521-3773
1433-7851
DOI: 10.1002/anie.201409620
Popis: 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 %.
Databáze: OpenAIRE
Externí odkaz: