Department 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.
Guangdong Provincial Key Laboratory of Brain Science, Disease and Drug Development, HKUST-Shenzhen Research Institute , Nanshan, Shenzhen 518057, China.
J Am Chem Soc. 2017 Jul 26;139(29):10150-10156. doi: 10.1021/jacs.7b05792. Epub 2017 Jul 18.
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 Hg 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.
（Z）-和（E）-几何异构体在生命和材料科学中发挥着重要但不同的作用。设计新的（Z）-/（E）-异构体并研究它们的性质、行为和相互作用在分子工程中至关重要。然而，它们的分离和结构确认的困难限制了它们在结构多样性和功能方面的应用范围。在本文所描述的工作中，我们成功地合成了具有聚集诱导发光特性的脲嘧啶二酮功能化四苯乙烯（（Z）-TPE-UPy 和（E）-TPE-UPy）的纯异构体，以及脲嘧啶二酮的超分子聚合性。它们的结构通过二维 COSY 和 NOESY NMR 光谱得到证实。两种异构体在聚集态下表现出明显的荧光：（Z）-TPE-UPy 发出绿色荧光，而其（E）-对应物则发出蓝色荧光。（Z）-TPE-UPy 中两个脲嘧啶二酮基团形成的空腔使其适合用于汞检测，而（E）-TPE-UPy 制备的高分子量聚合物可用于从其氯仿溶液中制备高荧光纤维和 2D/3D 光图案。
