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In Situ Visualization of Reversible Diels–Alder Reactions with Self-Reporting Aggregation-Induced Emission Luminogens

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journal contribution
posted on 07.01.2022, 13:41 authored by Danning Hu, Liucheng Mao, Mengshi Wang, Hongye Huang, Renjian Hu, Haijun Ma, Jinying Yuan, Yen Wei
The dynamic reversible Diels–Alder (DA) reactions play essential roles in both academic and applied fields. Currently, in situ visualization and direct monitoring of the formation and cleavage of covalent bonds in DA reactions are hampered by finite compatibility and expensive precise instruments, especially limited in solid reactions. We herein report a fluorescence system capable of in situ visualization by naked eyes and monitoring DA/retro-DA reactions. With the fluorescence quenching effect, the synthesized TPEMI could work as an innovative self-indicator for both DA termination and retro-DA occurrence. The fluorescence increases during DA reactions, and the mechanism is investigated to establish qualitative and quantitative relations. Besides rapid screening of reaction conditions and monitoring of DA exchange processes, the TPEMI fluorescence system can visualize heterogeneous and solid-state reactions with the AIE character. The TPEMI platform is expected to offer novel insights into reversible DA processes and dynamic covalent chemistry.