Journal
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY
Volume 139, Issue 29, Pages 10150-10156Publisher
AMER CHEMICAL SOC
DOI: 10.1021/jacs.7b05792
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Funding
- National Basic Research Program of China (973 Program) [2013CB834701, 2013CB834702]
- University Grants Committee of Hong Kong [AoE/P-03/08]
- Research Grants Council of Hong Kong [16301614, 16305015, C2014-15G, N_HKUST604/14]
- Innovation and Technology Commission [ITC-CNERC14SC01]
- Guangdong Innovative Research Team Program of China [201101C0105067115]
- Science and Technology Plan of Shenzhen [JCYJ20160229205601482]
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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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