Design, Synthesis, and Applications of a Novel Fluoride Probe Based on Isoquinolinium Salt
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esign, Synthesis, and Applications of a Novel Fluoride Probe Based on Isoquinolinium Salt Yeting Zhua, Yajun Yua, Yun-Hui Zhaoa,b,*, Zilong Tanga, and Li Tianc,** a Hunan
Provincial Key Laboratory of Controllable Preparation and Functional Application of Fine Polymers, School of Chemistry and Chemical Engineering, Hunan University of Science and Technology, Xiangtan, Hunan, 411201 China b National Engineering Laboratory for Wheat and Corn Further Processing, Henan University of Technology, Zhengzhou, 450001 China c School of Materials Science and Engineering, Hunan University of Science and Technology, Xiangtan, 411201 China e-mail: *[email protected]; **[email protected] Received April 28, 2020; revised May 18, 2020; accepted May 18, 2020
Abstract—A novel ratiometric fluorescent fluoride probe based on isoquinolinium salts has been designed and synthesized. According to the qualitative and quantitative studies the chemosensor has high selectivity and sensitivity to fluoride. Fluoride induces deprotection of the silyl protecting group of the hydroxyl group and causes a significant change in emission wavelength. The relative fluorescent intensity (I435/I540) increases linearly with F– concentration in the range of 0–10.0 μmol/L. The dynamic determination process is monitored by 1H NMR spectroscopy. Keywords: fluoride determination, ratiometric chemosensor, isoquinolinium salts, deprotection
DOI: 10.1134/S1070363220080204 INTRODUCTION Fluoride ion is an important trace element in humans and other mammals in maintaining physiological processes [1–3]. Fluoride is easily absorbed by the body, however, excessive accumulation of fluoride in the body can cause acute stomach and kidney diseases, skeletal fluorosis and even death [4]. The U.S. Environmental Protection Agency recommends its tolerance level of 4 mg/L in drinking water [5]. In view of the powerful physiological function of F– and the harm caused by its overdose, it is of high significance to develop a new probe that would be operation-simple, cost-effective and characterized by fast recognition of F–. Isoquinoline and its derivatives autofluorescence is not very strong, but their nitrogen atom alkylation into the corresponding isoquinolinium salts results in fluorescence wavelength red-shift and intensity significant increase [6, 7]. Therefore, the isoquinolinium salt can be used as a dye or a molecular probe. It is well known that the push-pull electron effect of substituents in dye conjugate systems has a great influence on the fluorescence emission wavelength. The hydroxyl group electron-donating effect in the conjugated systems depends significantly upon its protected or
unprotected character, which courses a pronounced shift of the emission wavelength of the fluorescent molecules [8, 9]. Accordingly many probe molecules with different recognition groups attached to their oxygen are used in qualitative recognition and quantitative evaluation of various target molecules [10–16]. This paper is devoted to design and synthesis of isoquinoline salts containin
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