Journal of the American Chemical Society
Journal of the American Chemical Society
4 years ago

Molecular Face-Rotating Cube with Emergent Chiral and Fluorescence Properties

Molecular Face-Rotating Cube with Emergent Chiral and Fluorescence Properties
Yu Wang, Xinchang Wang, Zhihao Li, Xiaoyu Cao, Hongxun Fang, Hang Qu, Zhongqun Tian
Chiral cage compounds are mainly constructed from chiral precursors or based on the symmetry breaking during coordination-driven self-assembly. Herein, we present a strategy to construct chiral organic cages by restricting the P or M rotational configuration of tetraphenylethylene (TPE) faces through dynamic covalent chemistry. The combination of graph theory, experimental characterizations and theoretical calculations suggests emergent chirality of cages is originated from complex arrangements of TPE faces with different orientational and rotational configurations. Accompanied by the generation of chirality, strong fluorescence also emerged during cage formation, even in dilute solutions with various solvents. In addition, the circularly polarized luminescence of the cages is realized as a synergy of their dual chiral and fluorescence properties. Chirality and fluorescence of cages are remarkably stable, because intramolecular flipping of phenyl rings in TPE faces is restricted, as indicated by calculations. This study provides insight into construct chiral cages by the rational design through graph theory, and might facilitate further design of cages and other supramolecular assemblies from aggregation-induced emission active building blocks.

Publisher URL: http://dx.doi.org/10.1021/jacs.7b07657

DOI: 10.1021/jacs.7b07657

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