Dramatic Differences in Aggregation-Induced Emission and Supramolecular Polymerizability of Tetraphenylethene-Based Stereoisomers
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 Hg 2+ 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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- Authors
- Peng, H.-Q., Zheng, X., Han, T., Kwok, R. T. K., Lam, J. W. Y., Huang, X., & Tang, B. Z.
- Affiliations
- Hong Kong University of Science and Technology (HK)
- Corresponding author
- Tang, Ben Zhong
- ORCID
- Venue
- Journal of the American Chemical Society
- Publisher
- American Chemical Society (ACS)
- Published
- 2017-07-18
- Volume
- 139
- Issue
- 29
- Pages
- 10150-10156
- ISSN
- 0002-7863 (ISSN-L)
- 1520-5126
- OpenAlex
- W2735822480
- Cited by
- 201
- References
- 82
- Citations by year
- 2026: 12 · 2025: 7 · 2024: 16 · 2023: 19 · 2022: 25 · 2021: 20 · 2020: 33 · 2019: 31 · 2018: 36 · 2017: 2
- FWCI
- 11.77
- Type
- journal article
- Language
- en
- Open access
- closed
- Locations
- Journal of the American Chemical Society (publishedVersion)
- PubMed (publishedVersion)
- Rare & Special e-Zone (The Hong Kong University of Science and Technology) (submittedVersion)
- Funders
- Research Grants Council, University Grants Committee (16301614, 16305015, C2014-15G, N_HKUST604/14)
- Ministry of Science and Technology of the People's Republic of China (2013CB834701, 2013CB834702)
- University Grants Committee (AoE/P-03/08)
- Innovation and Technology Commission (TCCNERC14SC01)
- Shenzhen Science and Technology Innovation Committee (JCYJ20160229205601482)
- Guangdong Province (201101C0105067115)
- Topics
- Physical Sciences › Materials Science › Materials Chemistry › Luminescence and Fluorescent Materials
- Physical Sciences › Chemistry › Organic Chemistry › Supramolecular Chemistry and Complexes
- Physical Sciences › Materials Science › Biomaterials › Supramolecular Self-Assembly in Materials
- Keywords
- tetraphenylethylene, ureidopyrimidinone, cis-trans isomers, stereoisomers, aggregation-induced emission, supramolecular polymerization, fluorescent polymers, mercury ion detection, fluorescent fibers, photopatterning
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