Journal
ANALYST
Volume 145, Issue 22, Pages 7297-7302Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0an01551b
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Funding
- National Natural Science Foundation of China [21775096]
- Shanxi Province 1331 project Key Innovation Team Construction Plan Cultivation Team [2018-CT-1]
- 2018 Xiangyuan County Solid Waste Comprehensive Utilization Science and Technology Project [2018XYSDJS-05]
- Shanxi Province Foundation for Returnees [2017-026]
- Shanxi Collaborative Innovation Center of High Value-added Utilization of Coal-related Wastes [2015-10-B3]
- Shanxi Province Foundation for Selected [2019]
- Scientific and Technological Innovation Programs of Higher Education Institutions in Shanxi [2019L0031]
- Key R&D Program of Shanxi Province [201903D421069]
- Shanxi Province Science Foundation [201901D111015]
- Scientific Instrument Center of Shanxi University [201512]
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Based on its reducibility, the double bond can act as a reaction site for hypochlorous acid (HOCl), which had been demonstrated by a great deal of work. Nevertheless, the reactivity is influenced by the adjacent chemical environment. Therefore, in this work, we constructed a probe (QI) by methoxy-substituted quinoline conjugating dicyanoisoflurone, in which dicyano and pyridine N act as electron-withdrawing groups and the methoxy acts as an electron-donating group, to regulate their adjacent C=C reactivity. The push-pull electron effect between the methoxy group and the pyridine N led to the C=C bond being passivated. On the other hand, another C=C bond was activated by the strong electron-pulling effect of the dicyano group. Thus, the previously weak intramolecular charge transfer became stronger after the dicyano adjacent to the C=C was oxidized by HOCl, and showed a strong emission shifted from 570 to 520 nm along with a color change. The reaction mechanism was verified by mass spectrometry, NMR and theoretical calculation, and further bioimaging demonstrated the practical application of the probe.
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