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Updated: Feb 27, 2026
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Published on: September 26, 2016
Dramatic Differences in Aggregation-Induced Emission and Supramolecular Polymerizability of Tetraphenylethene-Based
Hui-Qing Peng1,2, Xiaoyan Zheng1, Ting Han1,2
1Department of Chemistry, Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction, Institute of Molecular Functional Materials, Institute for Advanced Study, State Key Laboratory of Neuroscience, Division of Biomedical Engineering and Division of Life Science, The Hong Kong University of Science and Technology , Clear Water Bay, Kowloon, Hong Kong 999077, China.
Abstract:
Geometric (Z)- and (E)-isomers play important but different roles in life and material science. The design of new (Z)-/(E)- isomers and study of their properties, behaviors, and interactions are crucially important in molecular engineering. However, difficulties with their separation and structure confirmation limit their structural diversity and functionality in scope. In the work described herein, we successfully synthesized pure isomers of ureidopyrimidinone-functionalized tetraphenylethenes ((Z)-TPE-UPy and (E)-TPE-UPy), featuring both the aggregation-induced emission characteristic of tetraphenylethene and the supramolecular polymerizability of ureidopyrimidinone. Their structures were confirmed by 2D COSY and NOESY NMR spectroscopies. The two isomers show distinct fluorescence in the aggregate state: (Z)-TPE-UPy exhibits green emission, while its (E)-counterpart is blue-emitting. The cavity formed by the two ureidopyrimidinone groups of (Z)-TPE-UPy makes it suitable for Hg2+ detection, and the high-molecular-weight polymers prepared from (E)-TPE-UPy can be used to fabricate highly fluorescent fibers and 2D/3D photopatterns from their chloroform solutions.
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