Ring Reconstruction on a Trichalcogenasumanene Buckybowl: A Facile Approach to Donor–Acceptor‐Type [5‐6‐7] Fused Planar Polyheterocycles |
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Authors: | Xuexiang Li Yongtao Zhu Jiafeng Shao Lichuan Chen Sijie Zhao Baolin Wang Shangxi Zhang Yongliang Shao Prof. Dr. Hao‐Li Zhang Prof. Dr. Xiangfeng Shao |
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Affiliation: | 1. State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Tianshui Southern Road 222, Lanzhou 730000 (China);2. School of Physical Science and Technology, Lanzhou University, Tianshui Southern Road 222, Lanzhou 730000 (China) |
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Abstract: | 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 %. |
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Keywords: | arenes donor– acceptor systems fused‐ring systems oxidation structure elucidation |
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