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A novel fluorescent turn-on probe based on thiosemicarbazide-naphthalene for selectively detecting Zn2+

  • Materials (Organic, Inorganic, Electronic, Thin Films)
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Abstract

A new thiosemicarbazide-naphthalene-based fluorescent chemosensor FNC ((2-(furan-2-carbonyl)-N-(naphthalen-1-yl)hydrazine-1-carbothioamide)) for Zn2+ was synthesized and identified. FNC was applied to selectively detect Zn2+ with fluorescent turn-on response. The detection limit was determined to be 1.93 µM, which is much below the WHO standard (76.5 µM). The detecting mechanism of FNC to Zn2+ was revealed to bind FNC to Zn2+ in the proportion of 1: 1 by Job plot, ESI-mass and 1H NMR titrations. DFT and TD-DFT calculations were performed for FNC and FNC-Zn2+, which provide insight into structural, electronic and photophysical properties.

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References

  1. J. Briffa, E. Sinagra and R. Blundell, Heliyon, 6, e04691 (2020).

    CAS  PubMed  PubMed Central  Google Scholar 

  2. M. Ariannezhad, D. Habibi, S. Heydari and V. Khorramabadi, Korean J. Chem. Eng., 38, 1510 (2021).

    CAS  Google Scholar 

  3. M. Theetharappan and M. A. Neelakantan, J. Fluoresc., 31, 1277 (2021).

    CAS  PubMed  Google Scholar 

  4. P. Cheng, Y. Ren, L. Yang, R. Li, X. Wang, B. Li and H. Yuan, Korean J. Chem. Eng., 39, 3350 (2022).

    CAS  Google Scholar 

  5. Z. Long, Y. Huang, W. Zhang, Z. Shi, D. Yu, Y. Chen, C. Liu and R. Wang, Environ. Monit. Assess., 193 (2021).

  6. J. M. Jung, C. Kim and R. G. Harrison, Sens. Actuators B Chem., 255, 2756 (2018).

    CAS  Google Scholar 

  7. A. Pandith, N. Uddin, C. H. Choi and H. S. Kim, Sens. Actuators B Chem., 247, 840 (2017).

    CAS  Google Scholar 

  8. H. Xu, C. Zhu, Y. Chen, Y. Bai, Z. Han, S. Yao, Y. Jiao, H. Yuan, W. He and Z. Guo, Chem. Sci., 11, 11037 (2020).

    CAS  PubMed  PubMed Central  Google Scholar 

  9. D. Maity and T. Govindaraju, Chem. Commun., 48, 1039 (2012).

    CAS  Google Scholar 

  10. D. Choe and C. Kim, J. Chem. Sci., 133 (2021).

  11. X. Wu, Z. Zhang, H. Liu and S. Pu, RSC Adv., 10, 15547 (2020).

    CAS  PubMed  PubMed Central  Google Scholar 

  12. D. Xiang, S. Zhang, Y. Wang, K. Sun and H. Xu, Tetrahedron, 106–107, 132648 (2022).

    Google Scholar 

  13. B. Suh, D. Gil, S. Yoon, K.-T. Kim and C. Kim, Chemosensors, 10, 32 (2022).

    CAS  Google Scholar 

  14. Y. P. Zhang, W. Y. Niu, C. M. Ma, Y. S. Yang, H. C. Guo and J. J. Xue, Inorg. Chem. Commun., 130, 108735 (2021).

    CAS  Google Scholar 

  15. M. Mary Mathew and A. Sreekanth, Inorg. Chim. Acta, 516, 120149 (2021).

    CAS  Google Scholar 

  16. J. B. Chae, D. Yun, S. Kim, H. Lee, M. Kim, M. H. Lim, K. T. Kim and C. Kim, Spectrochim. Acta A Mol. Biomol. Spectrosc., 219, 74 (2019).

    CAS  PubMed  Google Scholar 

  17. M. Kiani, M. Bagherzadeh, S. Meghdadi, N. Rabiee, A. Abbasi, K. Schenk-Joß, M. Tahriri, L. Tayebi and T. J. Webster, New J. Chem., 44, 11841 (2020).

    CAS  Google Scholar 

  18. M. Ruz, F. Carrasco, P. Rojas, K. Basfi-fer, M. C. Hernández and A. Pérez, Biol. Trace Elem. Res., 188, 177 (2019).

    CAS  PubMed  Google Scholar 

  19. J. Y. Yun, T. G. Jo, J. Han, H. J. Jang, M. H. Lim and C. Kim, Sens. Actuators B Chem., 255, 3108 (2018).

    CAS  Google Scholar 

  20. J. H. Kang and C. Kim, Photochem. Photobiol. Sci., 17, 442 (2018).

    CAS  PubMed  Google Scholar 

  21. M.K. Swami and P.K. Gupta, Proc. Natl. Acad. Sci. India Sect. A - Phys. Sci., 88, 453 (2018).

    Google Scholar 

  22. N. A. S. Pungut, H. Mat Saad, K. S. Sim and K. W. Tan, J. Photochem. Photobiol. A Chem., 414, 113290 (2021).

    CAS  Google Scholar 

  23. S. Anbu, A. Paul, K. Surendranath, N. S. Solaiman and A. J. L. Pombeiro, Sens. Actuators B Chem., 337, 129785 (2021).

    CAS  Google Scholar 

  24. P. Bhalla, A. Goel, N. Tomer and R. Malhotra, Inorg. Chem. Commun., 136 (2022).

  25. M. X. Lv, L. Y. Bian, W. N. Wu, Z. H. Xu, Y. Wang, X. L. Zhao, Z. Q. Xu, Y. C. Fan and L. L. Yan, Color. Technol., 1 (2021).

  26. N. A. S. Pungut, M. P. Heng, H. M. Saad, K. S. Sim, V. S. Lee and K. W. Tan, J. Mol. Struct., 1238, 130453 (2021).

    CAS  Google Scholar 

  27. D. Y. Lee, N. Singh and D. O. Jang, Tetrahedron Lett., 51, 1103 (2010).

    CAS  Google Scholar 

  28. C. K. Maurya, U. Pathak and P. K. Gupta, Anal. Bioanal. Chem., 413, 4501 (2021).

    CAS  PubMed  Google Scholar 

  29. Y. Liu, X. Wang, E. Feng, C. Fan and S. Pu, Spectrochim. Acta A Mol. Biomol. Spectrosc., 246, 119052 (2021).

    CAS  PubMed  Google Scholar 

  30. M. S. Kim, D. Yun, J.B. Chae, H. So, H. Lee, K. Kim, M. Kim, M. H. Lim and C. Kim, Sensors, 19, 5458 (2019).

    CAS  PubMed  PubMed Central  Google Scholar 

  31. S. Jana, S. Prajapati, K. K. Suryavanshi, S. Goswami, R. Parida and S. Giri, J. Phys. Org. Chem., 33, 1 (2020).

    Google Scholar 

  32. Q. Lin, Y. Q. Fan, P. P. Mao, L. Liu, J. Liu, Y.M. Zhang, H. Yao and T. B. Wei, Chem. A Eur. J., 24, 777 (2018).

    CAS  Google Scholar 

  33. J. M. Jung, J. H. Kang, J. Han, H. Lee, M. H. Lim, K. T. Kim and C. Kim, Sens. Actuators B Chem., 267, 58 (2018).

    CAS  Google Scholar 

  34. J. H. Kang, J. Han, H. Lee, M. H. Lim, K. T. Kim and C. Kim, Dyes Pigm., 152, 131 (2018).

    CAS  Google Scholar 

  35. J. B. Chae, H. Lee and C. Kim, J. Fluoresc., 30, 347 (2020).

    CAS  PubMed  Google Scholar 

  36. J. Sun, T. Li, C. Liu, J. Xue, L. Tian, K. Liu, S. Li and Z. Yang, J. Photochem. Photobiol. A Chem., 406, 113007 (2021).

    CAS  Google Scholar 

  37. H. Taş, J. Adams, J. C. Namyslo and A. Schmidt, RSC Adv., 11, 36450 (2021).

    PubMed  PubMed Central  Google Scholar 

  38. N. Mudi, P. Hazra, M. Shyamal, S. Maity, P. K. Giri, S. S. Samanta, D. Mandal and A. Misra, J. Fluoresc., 31, 315 (2021).

    CAS  PubMed  Google Scholar 

  39. H. So, H. Cho, H. Lee, M. C. Tran, K. T. Kim and C. Kim, Microchem. J., 155, 104788 (2020).

    CAS  Google Scholar 

  40. F. P. Ying, H. S. Lu, X. Q. Yi, Y. Q. Xu and Y. Y. Lv, Sens. Actuators B Chem., 340 (2021).

  41. N. S. Mohamad, N. H. Zakaria, N. Daud, L. L. Tan, G. C. Ta, L. Y. Heng and N. I. Hassan, Sensors (Switzerland), 21, 1 (2021).

    Google Scholar 

  42. S. C. Lee, M. Lee, B. Suh, J. Lee and C. Kim, ChemistrySelect, 6, 8397 (2021).

    CAS  Google Scholar 

  43. B. K. Rani and S. A. John, J. Photochem. Photobiol. A Chem., 418, 113372 (2021).

    CAS  Google Scholar 

  44. M. Wu, D. D. Yang, H. W. Zheng, Q. F. Liang, J. Bin Li, Y. Kang, S. Li, C. Jiao, X. J. Zheng and L. P. Jin, Dalton Trans., 50, 1507 (2021).

    CAS  PubMed  Google Scholar 

  45. A. K. K. Bhasin, P. Chauhan and S. Chaudhary, Sens. Actuators B Chem., 330, 129328 (2021).

    CAS  Google Scholar 

  46. C. Jiang, L. Yang, P. Li, Y. Liu, S. Li, Y. Fu and F. Ye, Spectrochim. Acta A Mol. Biomol. Spectrosc., 263, 120168 (2021).

    CAS  PubMed  Google Scholar 

  47. S. Jiang, S. Chen, Z. Wang, H. Guo and F. Yang, Sens. Actuators B Chem., 308, 127734 (2020).

    CAS  Google Scholar 

  48. E. Bahojb Noruzi, M. Kheirkhahi, B. Shaabani, S. Geremia, N. Hickey, F. Asaro, P. Nitti and H. S. Kafil, Front. Chem., 7 (2019).

  49. K. H. Alharbi, Crit. Rev. Anal. Chem., 1 (2022).

  50. Z. Gao, S. Qiu, M. Yan, H. Liu, S. Lu, H. Lian, P. Zhang, J. Zhu and M. Jin, J. Mol. Struct., 1254, 132312 (2022).

    CAS  Google Scholar 

  51. A. Jayaraj, M. S. Gayathri, G. Sivaraman and C. A. S. P, J. Photochem. Photobiol. B Biol., 226, 112371 (2022).

    CAS  Google Scholar 

  52. S. Paul and P. Banerjee, Sens. Actuators B Chem., 329, 129172 (2021).

    CAS  Google Scholar 

  53. Gaussian 16, Revision C.01, M. J. Frisch, G. W. Trucks, H. B. Schlegel, G.E. Scuseria, M.A. Robb, J.R. Cheeseman, G. Scalmani, V. Barone, G. A. Petersson, H. Nakatsuji, X. Li, M. Caricato, A. V. Marenich, J. Bloino, B. G. Janesko, R. Gomperts, B. Mennucci, H. P. Hratchian, J. V. Ortiz, A. F. Izmaylov, J. L. Sonnenberg, D. Williams-Young, F. Ding, F. Lipparini, F. Egidi, J. Goings, B. Peng, A. Petrone, T. Henderson, D. Ranasinghe, V. G. Zakrzewski, J. Gao, N. Rega, G. Zheng, W. Liang, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, T. Vreven, K. Throssell, J.A. Montgomery Jr., J. E. P., F. Ogliaro, M. J. Bearpark, J. J. Heyd, E. N. Brothers, K. N. Kudin, V. N. Staroverov, T. A. Keith, R. Kobayashi, J. Normand, K. Raghavachari, A. P. Rendell, J. C. Burant, S. S. Iyengar, J. Tomasi, M. Cossi, J. M. Millam, M. Klene, C. Adamo, R. Cammi, J. W. Ochterski, R. L. Martin, K. Morokuma, O. Farkas, J. B. Foresman and D. J. Fox, Gaussian, Inc., Wallingford CT (2016).

  54. A. D. Becke, J. Chem. Phys., 98, 5648 (1993).

    CAS  Google Scholar 

  55. M. M. Francl, W. J. Pietro, W. J. Hehre, J. S. Binkley, M. S. Gordon, D. J. DeFrees and J. A. Pople, J. Chem. Phys., 77, 3654 (1982).

    CAS  Google Scholar 

  56. P. C. Hariharan and J. A. Pople, Theor. Chim. Acta, 28, 213 (1973).

    CAS  Google Scholar 

  57. P. J. Hay and W. R. Wadt, J Chem. Phys., 82, 299 (1985).

    CAS  Google Scholar 

  58. A. Klamt, C. Moya and J. Palomar, J. Chem. Theory Comput., 11, 4220 (2015).

    CAS  PubMed  Google Scholar 

  59. A. M. Brouwer, Pure Appl. Chem., 83, 2213 (2011).

    CAS  Google Scholar 

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Acknowledgement

The National Research Foundation of Korea (2018R1A2B6001686) is gratefully acknowledged.

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Correspondence to Cheal Kim.

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Additional information as noted in the text. This information is available via the Internet at http://www.springer.com/chemistry/journal/11814.

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Lee, M., Moon, S., Gil, D. et al. A novel fluorescent turn-on probe based on thiosemicarbazide-naphthalene for selectively detecting Zn2+. Korean J. Chem. Eng. 40, 2010–2016 (2023). https://doi.org/10.1007/s11814-023-1464-5

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  • DOI: https://doi.org/10.1007/s11814-023-1464-5

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