期刊
SCIENCE CHINA-CHEMISTRY
卷 61, 期 1, 页码 76-87出版社
SCIENCE PRESS
DOI: 10.1007/s11426-017-9147-0
关键词
AIE; ESIPT; electronic effect; proton activity; ion sensor
资金
- National Natural Science Foundation of China [51673118, 51273053]
- Key Project of the Ministry of Science and Technology of China [2013CB834702]
- Natural Science Fund of Guangdong Province [2014A030313659, 2014A030306035, 2016A030312002]
- Fundamental Research Funds for the Central Universities [2015ZY013, 2017JQ013]
- Innovation and Technology Commission of Hong Kong [ITC-CNERC14SC01]
- Science and Technology Plan of Shenzhen [JCYJ20160428150429072]
- Guangdong Innovative Research Team Program [201101C0105067115]
Two novel AIE-active salicylaldehyde azine (SAA) derivatives with a typical excited-state intramolecular proton transfer (ESIPT) process are prepared by introducing electron-withdrawing and donating groups at para-position of phenolic hydroxyl group (CN-SAA and TPA-SAA). The effect of the proton activity in SAA framework on their optical behaviors is investigated spectroscopically. The results from NMR and solvation measurements show that the proton of phenolic hydroxyl group has higher activity when there are electron-withdrawing groups, and the absorption and fluorescence spectra in buffers with different pH also provide the same results. After inviting F- as a nucleophilic probe, this proton activity difference in CN-SAA and TPA-SAA becomes more obvious. The potential application of both molecules is investigated. TPA-SAA exhibits good quantitative sensing ability towards F- with a fluorescence turn-on mode, whereas the aggregates of TPA-SAA can selectively and sensitively detect Cu2+ in aqueous solution. From these results, a structure-property relationship is established: the occurrence of ESIPT process will become much easier when linking electron-withdrawing groups at the para-position of phenolic hydroxyl group (e.g., CN-SAA), and it is better to introduce electron-donating groups to enhance the sensing ability towards ions (e.g., TPA-SAA). This work will provide guidance for further design and preparation of AIE-active luminogens with ESIPT process for sensing applications.
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