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Design, Synthesis, and Applications of a Novel Fluoride Probe Based on Isoquinolinium Salt

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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.

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REFERENCES

  1. Jagtap, S., Yenkie, M.K., Labhsetwar, N., and Rayalu, S., Chem. Rev., 2012, vol. 112, p. 2454. https://doi.org/10.1021/cr2002855

  2. Zhou, Y., Zhang, J.F., and Yoon, J., Chem. Rev., 2014, vol. 114, p. 5511. https://doi.org/10.1021/cr400352m

  3. Li, Y., Duan, Y., Zheng, J., Li, J., Zhao, W., Yang, S., and Yang, R., Anal. Chem., 2013, vol. 85, p. 11456. https://doi.org/10.1021/ja908215t

  4. Refsnes, M., Schwarze, P.E., Holme, J.A., and Lag, M., Hum. Exp. Toxicol., 2003, vol. 22, p. 111. https://doi.org/10.1191/0960327103ht322oa

  5. Fawell, J., Bailey, K., Chilton, J., Dahi, E., and Magara, Y., WHO Drinking-Water Quality Series, Fluoride in Drinking-Water, London: IWA Publishing, 2006.

  6. Tang, Y., Yu, Y., Wei, X., Yang, J., Zhu, Y., Zhao, Y.H., Tang, Z., Zhou, Z., Li, X., and Yu, X., Tetrahedron Lett., 2019, vol. 60. https://doi.org/10.1016/j.tetlet.2019.151187

  7. Xu, J., Zhang, Y., Yu, H., Gao, X., and Shao, S., Anal. Chem., 2016, vol. 88, p. 1455. https://doi.org/10.1021/acs.analchem.5b04424

  8. Ren, T., Xu, W., Zhang, Q., Zhang, X., Wen, S., Yi, H., Yuan, L., and Zhang. X., Angew. Chem. Int. Ed., 2018, vol. 57, p. 7473. https://doi.org/10.1002/anie.201800293

  9. Zhao, Y.H., Luo, Y., Wang, H., Wei, H., Guo, T., Tan, H., Yuan, L., and Zhang, X.-B., Anal. Chim. Acta, 2019, vol. 1065, p. 134. https://doi.org/10.1016/j.aca.2019.03.029

    Article  CAS  PubMed  Google Scholar 

  10. Gabrielli, L., and Mancin, F., J. Org. Chem., 2016, vol. 81, p. 10715. https://doi.org/10.1021/acs.joc.6b01787

  11. Hisamatsu, S., Suzuki, S., Kohmoto, S., Kishikawa, K., Yamamoto, Y., Motokawa, R., and Yaita, T., Tetrahedron, 2017, vol. 73, p. 3993. https://doi.org/10.1016/j.tet.2017.05.084

    Article  CAS  Google Scholar 

  12. Turan, S. and Akkaya, E.U., Org. Lett., 2014, vol. 16, p. 1680. https://doi.org/10.1021/ol5003412

  13. Shi, X., Fan, W., Fan, C., Lu, Z., Bo, Q., Wang, Z., Black, C.A., Wang, F., and Wang, Y., Dyes Pigments, 2017, vol. 140, p. 109. https://doi.org/10.1016/j.dyepig.2017.01.038

  14. Zhao, Y.H., Li, Y., Long, Y., Zhou, Z., Tang, Z., Deng, K., and Zhang, S., Tetrahedron Lett., 2017, vol. 58, p. 1351. https://doi.org/10.1016/j.tetlet.2017.02.066

    Article  CAS  Google Scholar 

  15. Wu, Z. and Tang, X., Anal. Chem., 2015, vol. 87, p. 8613. https://doi.org/10.1021/acs.analchem.5b02578

  16. Li, W., Gong, X., Fan, X., Yin, S., Su, D., Zhang, X., and Yuan, L., Chin. Chem. Lett., 2019, vol. 30, p. 1775. https://doi.org/10.1016/j.cclet.2019.07.056

    Article  CAS  Google Scholar 

  17. Ye, Z.S., Guo, R.N., Cai, X.F., Chen, M.W., Shi, L., and Zhou, Y.G., Angew. Chem. Int. Ed., 2013, vol. 52, p. 3685. https://doi.org/10.1002/anie.201208300

  18. Zhao, Y.H., Yu, Y., Hu, D., Zhao, L., Xie, W., and Zhou, Z., Asian J. Org. Chem., 2020, vol. 9, p. 953. https://doi.org/10.1002/ajoc.202000202

    Article  CAS  Google Scholar 

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Funding

The generous financial support from the National Natural Science Foundation of China (nos. 51773057 and 21877034), the Hunan Provincial Education Department Scientific Research Fund (no. 18B221) are gratefully acknowledged.

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Authors and Affiliations

  1. 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, 411201, Hunan, China

    Yeting Zhu, Yajun Yu, Yun-Hui Zhao & Zilong Tang

  2. National Engineering Laboratory for Wheat and Corn Further Processing, Henan University of Technology, 450001, Zhengzhou, China

    Yun-Hui Zhao

  3. School of Materials Science and Engineering, Hunan University of Science and Technology, 411201, Xiangtan, China

    Li Tian

Authors
  1. Yeting Zhu
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  2. Yajun Yu
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  3. Yun-Hui Zhao
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  4. Zilong Tang
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  5. Li Tian
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Correspondence to Yun-Hui Zhao or Li Tian.

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Zhu, Y., Yu, Y., Zhao, YH. et al. Design, Synthesis, and Applications of a Novel Fluoride Probe Based on Isoquinolinium Salt. Russ J Gen Chem 90, 1518–1522 (2020). https://doi.org/10.1134/S1070363220080204

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