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A New Fluoride Chemodosimeter Based on 3-Ether-Substituted 1, 8-Naphthalimide Derivatives

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Abstract

We developed a new chromogenic and fluorescent "off–on" 1, 8-naphthalimide-derivated chemosensor 1 based on an F–-triggered desilylation reaction. It showed significant variations in UV/visible absorption (510 nm) and fluorescence emission wavelength (580 nm) for selective detection of fluorides in THF/H2O system (v/v, 50:50). Moreover, chemodosimeter 1-loaded test strips were successfully fabricated todetect fluorides efficiently.

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References

  1. Zhou Y, Zhang JF, Yoon J (2014) Fluorescence and colorimetric chemosensors for fluoride-ion detection. Chem Rev 114:5511–5571

    Article  CAS  Google Scholar 

  2. Craig L, Lutz A, Berry KA, Yang W (2015) Recommendations for fluoride limits in drinking water based on estimated daily fluoride intake in the Upper East Region. Ghana Sci Total Environ 532:127–137

    Article  CAS  Google Scholar 

  3. Zhang LE, Huang D, Yang J (2017) Probabilistic risk assessment of Chinese residents’ exposure to fluoride in improved drinking water in endemic fluorosis areas. Environ Pollut 222:118–125

    Article  CAS  Google Scholar 

  4. Lin YJ, Lin C, Yeh KJ, Lee A (2000) Photodegradation of the Herbicides Butachlor and Ronstar Using Natural Sunlight and Diethylamine. Bull Environ Contam Toxicol 64(6):780–785

    Article  CAS  Google Scholar 

  5. Perumal E, Paul V, Govindarajan V, Panneerselvam L (2013) A brief review on experimental fluorosis. Toxicol Lett 223(2):236–251

    Article  CAS  Google Scholar 

  6. Yu X, Chen J, Li Y (2018) Threshold effects of moderately excessive fluoride exposure on children’s health: A potential association between dental fluorosis and loss of excellent intelligence. Environ Int 118:116–124

    Article  CAS  Google Scholar 

  7. Ding WH, Wang D, Zheng XJ (2015) A turn-on fluorescence chemosensor for Al3+, F− and CN− ions, and its application in cell imaging. Sens Actuat B Chem 209:359–367

    Article  CAS  Google Scholar 

  8. Diao Q, Ma P, Lv L (2016) A water-soluble and reversible fluorescent probe for Al 3+ and F − in living cells. Sens Actuat B Chem 229:138–144

    Article  CAS  Google Scholar 

  9. Kim Y, Gabbaie FP (2009) Cationic Boranes for the Complexation of Fluoride Ions in Water below the 4 ppm Maximum Contaminant Level. J Am Chem Soc 131:3363–3369

    Article  CAS  Google Scholar 

  10. Rosen CB, Hansen DJ, Gothelf KV (2013) Efficient colorimetric and fluorescent detection of fluoride in DMSO-water mixtures with arylaldoximes. Org Biomol Chem 11:7916–7922

    Article  CAS  Google Scholar 

  11. Peng XJ, Wu YK, Fan JL, Tian MZ, Han KL (2005) Colorimetric and ratiometric fluorescence sensing of fluoride: Tuning selectivity in proton transfer. J Org Chem 70:10524–10531

    Article  CAS  Google Scholar 

  12. Madhu S, Ravikanth M (2014) Boron-dipyrromethene based reversible and reusable selective chemosensor for fluoride detection. Inorg Chem 53:1646–1653

    Article  CAS  Google Scholar 

  13. Renuga D, Udhayakumari D, Suganya S, Velmathi S (2012) Novel thiophene based colorimetric and fluorescent receptor for selective recognition of fluoride ions. Tetrahedron Lett 53:5068–5070

    Article  CAS  Google Scholar 

  14. Chen J, Liu C, Zhang J, Ding W, Zhou M, Wu F (2013) A novel chemodosimeter for fluoride ions based on deprotonation of the C-H group followed by an autoxidative decyanation process. Chem Commun 49:10814–10816

    Article  CAS  Google Scholar 

  15. Zhou M, Chen J, Liu C (2014) Anion binding modes in cis-trans-isomers of a binding site-fluorophore-pi-extended system. Chem Commun 50:14748–14751

    Article  CAS  Google Scholar 

  16. Fu L, Jiang FL, Fortin D, Harvey PD, Liu Y (2011) A reaction-based chromogenic and fluorescent chemodosimeter for fluoride anions. Chem Commun 47:5503–5505

    Article  CAS  Google Scholar 

  17. Buckland D, Bhosale SV, Langford SJ (2011) A chemodosimer based on a core-substituted naphthalene diimide for fluoride ion detection. Tetrahedron Lett 52:1990–1992

    Article  CAS  Google Scholar 

  18. Zhou J, Wu B, Zhou Z, Tian J, Yuan A (2019) A Novel Naphthalene-Fused Boron Dipyrromethene (BODIPY)-Based Near Infrared Fluorescent Probe for Detecting Fluoride in Living Cells. Chin J Org Chem 39

  19. Ji K, Wu H, Chen J (2016) A selective chromofluorogenic chemodosimeter for fluoride ions based on distyrylbenzenes derivatives containing dual Si-O groups. Luminescence 31:924–928

    Article  CAS  Google Scholar 

  20. Ren J, Wu Z, Zhou Y, Li Y, Xu Z (2011) Colorimetric fluoride sensor based on 1, 8-naphthalimide derivatives. Dyes Pigm 91:442–445

    Article  CAS  Google Scholar 

  21. Hu Q, Huang Q, Mao Y (2019) A near-infrared large Stokes shift probe based enhanced ICT strategy for F- detection in real samples and cell imaging. Tetrahedron 75:130762

  22. Li B, Zhang C, Wang Y (2015) Chromogenic and fluorescent “turn-on” chemodosimeter for fluoride based on a F(-)-triggered cascade reaction. Luminescence 30:699–702

    Article  CAS  Google Scholar 

  23. Shi J, Shu W, Wu Y, **g J, Zhang R, Zhang X (2019) A highly colorimetric and ratiometric fluorescent probe for the detection of fluoride ions using test strips. Anal Methods 11:3844–3850

    Article  CAS  Google Scholar 

  24. Liu C, Liu Z, Zhu T, Fu C, Gao C, Chen X (2021) Synthesis and Recognition Properties of Fluoroborodipyrrole Fluorescent Probes Based on Fluorine Triggered Cascade Releasing. Chin J Org Chem 41:303–309

    Article  Google Scholar 

  25. Cheng W, Xue X, Gan L (2021) Individual and successive detection of H2S and HClO in living cells and zebrafish by a dual-channel fluorescent probe with longer emission wavelength. Anal Chim Acta 1156:338362

  26. Zhong K, Hu X, Zhou S (2021) Mitochondria-Targeted Red-Emission Fluorescent Probe for Ultrafast Detection of H2S in Food and Its Bioimaging Application. J Agric Food Chem 69:4628–4634

    Article  CAS  Google Scholar 

  27. Wang WX, Jiang WL, Mao GJ (2021) Monitoring the Fluctuation of Hydrogen Peroxide in Diabetes and Its Complications with a Novel Near-Infrared Fluorescent Probe. Anal Chem 93:3301–3307

    Article  CAS  Google Scholar 

  28. Luo X, Cheng Z, Wang R, Yu F (2021) Indication of Dynamic Peroxynitrite Fluctuations in the Rat Epilepsy Model with a Near-Infrared Two-Photon Fluorescent Probe. Anal Chem 93:2490–2499

    Article  CAS  Google Scholar 

  29. Luo ZW, Yang B, Zhong C, Tang F, Yuan M, Xue YB, Yao GM, Zhang JW, Zhang YH (2013) A dual-channel probe for selective fluoride determination and application in live cell imaging. Dyes Pigm 97:52–57

    Article  CAS  Google Scholar 

  30. Pettit GR, Grealish MP, Jung MK (2002) Antineoplastic Agents. 465. Structural Modification of Resveratrol: SodiumResverastatin Phosphate. J Med Chem 45:2534–2542

    Article  CAS  Google Scholar 

  31. Chen L, Fu C, Li Z (2020) A new strategy for sensing cyanide ions by cyanide-induced nucleophilic substitution of hydrogen in nitro-controlled electron-deficient fluorophores. Tetrahedron Lett 61:151656

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Acknowledgements

We thank the Natural Science Foundation of Shanghai (No. 17ZR1429900) and the Opening Fund of Shanghai Key Laboratory of Chemical Biology for financial support.

Funding

The Natural Science Foundation of Shanghai (No. 17ZR1429900) and the Opening Fund of Shanghai Key Laboratory of Chemical Biology.

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Authors and Affiliations

  1. School of Chemical and Environmental Engineering, Shanghai Institute of Technology, 201418, Shanghai, P. R. China

    ** Chen, Haibing Shao, Tingting Zhu, Zhihua Chen, Yan Hu, Hua Zhang & Chuanxiang Liu

Authors
  1. ** Chen
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  2. Haibing Shao
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  3. Tingting Zhu
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  4. Zhihua Chen
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  5. Yan Hu
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  6. Hua Zhang
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  7. Chuanxiang Liu
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Contributions

All authors contributed to the study conception and design. ** Chen carried out the experiments, Haibin Shao, Tingting Zhu, Zhihua Chen and Yan Hu conducted the data analyses, Hua Zhang and Chuanxiang Liu wrote and edited the paper.

Corresponding author

Correspondence to Chuanxiang Liu.

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Highlights

• A new sensor based on an F–-triggered desilylation reaction.

• The probe 1 test strips exhibited efficiently detection of fluorides with significant changes in fluorescence.

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Supplementary file1 (DOCX 26667 KB)

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Cite this article

Chen, X., Shao, H., Zhu, T. et al. A New Fluoride Chemodosimeter Based on 3-Ether-Substituted 1, 8-Naphthalimide Derivatives. J Fluoresc 32, 921–926 (2022). https://doi.org/10.1007/s10895-021-02871-5

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  • DOI: https://doi.org/10.1007/s10895-021-02871-5

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