Spatial organization of chromophores is of crucial importance in governing energy-transfer processes and hence the performance of devices that exploit such energy flows. Studying EET processes in systems with the donor and acceptor connected by covalent bonds has provided most of the fundamental advances in this field. 14,16 However, with the evolution of energy-transfer systems toward increasingly large, sophisticated donor−acceptor assemblies, the reliance on covalent linking becomes increasingly untenable. 17 Noncovalent interactions, including van der Waals, hydrophobic, π−π, dipole, and metal ligation, may provide limitless possibilities to construct self-assembled architectures for various applications without time-consuming synthesis. 18 Indeed, nature relies to a large extent on such noncovalent interactions to perform a variety of sophisticated biological functions. The best-known examples include protein
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.
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