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Synthesis, characterization, Density Functional Theory (DFT) calculation, and fluorescent study of an efficient and novel Schiff base Cu(II) sensor

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Abstract

A Schiff base fluorescent “turn-off” sensor L based on 2, 4-diamino-6-hydroxypyrimidine, and 2-hydroxy-1-naphthaldehyde was synthesized, which shows excellent selectivity and sensitivity towards Cu2+ ions in an aqueous medium. The detection limit of the probe was found to be 11.92 µM which is much lower than the acceptable level of Cu2+ ions in drinking water as set by the World Health Organization (30 µM) and the U. S. Environmental Protection Agency (20 µM). Furthermore, a 1: 0.5 binding stoichiometry between the probe and Cu2+ ion was confirmed from the fluorescence titration data, Job’s plot, and DFT calculation. The binding constant (Ka) of Cu2+ ion with the probe was found to be 6.3 × 104 M−1. Thus, the overall study reveals that the synthesized Schiff base ligand is a potential fluorescent sensor for Cu2+ions.

Graphical abstract

The research study includes the synthesis of a novel and efficient Schiff base ligand L, which is highly sensitive and a selective fluorescent sensor for Cu2+ ions with a very low detection limit.

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References

  1. World Health Organization WHO and World Health Organisation Staff 2004 Guidelines for Drinking-water Quality Vol. 1 World Health Organization.

  2. Schriks M, Heringa M B, van der Kooi M M, de Voogt P and van Wezel A P 2010 Toxicological relevance of emerging contaminants for drinking water quality Water Res. 44 461

    Article  CAS  Google Scholar 

  3. Arruti A, Fernández-Olmo I and Irabien Á 2010 Evaluation of the contribution of local sources to trace metals levels in urban PM2. 5 and PM10 in the Cantabria region (Northern Spain) J. Environ. Monit. 12 1451

  4. Huff J, Lunn R M, Waalkes M P, Tomatis L and Infante P F 2007 Cadmium-induced cancers in animals and in humans Int. J. Occup. Environ. Health 13 202

    Article  CAS  Google Scholar 

  5. Bhatti P, Stewart P A, Hutchinson A, Rothman N, Linet M S, Inskip P D and Rajaraman P 2009 Lead exposure, polymorphisms in genes related to oxidative stress, and risk of adult brain tumors Cancer Epidemiol. Biomark. Prev. 18 1841

    Article  CAS  Google Scholar 

  6. De Acha N, Elosúa C, Corres J M and Arregui F J 2019 Fluorescent sensors for the detection of heavy metal ions in aqueous media Sensors 19 599

    Article  Google Scholar 

  7. Vendrell M, Zhai D, Er J C and Chang Y T 2012 Combinatorial strategies in fluorescent probe development Chem. Rev. 112 4391

    Article  CAS  Google Scholar 

  8. Bell T W and Hext N M 2004 Supramolecular optical chemosensors for organic analytes Chem. Soc. Rev. 33 589

    CAS  PubMed  Google Scholar 

  9. Mao J, Wang L, Dou W, Tang X, Yan Y and Liu W 2007 Tuning the selectivity of two chemosensors to Fe (III) and Cr (III) Org. Lett. 9 4567

    Article  CAS  Google Scholar 

  10. Gale P A, García-Garrido S E and Garric J 2008 Anion receptors based on organic frameworks: highlights from 2005 and 2006 Chem. Soc. Rev. 37 151

    Article  CAS  Google Scholar 

  11. Lakowicz J R 2013 Principles of Fluorescence Spectroscopy J R Lakowicz (Ed.) p.1.

  12. Vogel A I, Furniss B S, Hannaford A J, Smith P W and Tatchell A R 1989 Vogel’s Textbook of Practical Organic Chemistry (Pearson Education India: Location)

    Google Scholar 

  13. Kumar J, Rai A and Raj V 2017 A comprehensive review on the pharmacological activity of Schiff base containing derivatives OMCIJ 1 88

    Google Scholar 

  14. Guo Z, Niu Q, Li T, Sun T and Chi H 2019 A fast, highly selective and sensitive colorimetric and fluorescent sensor for Cu2+ and its application in real water and food samples Spectrochim. Acta A Mol. Biomol. Spectrosc. 213 97

    Article  CAS  Google Scholar 

  15. Kang J H, Lee S Y, Ahn H M and Kim C 2016 Sequential detection of copper (II) and cyanide by a simple colorimetric chemosensor Inorg. Chem. Commun. 74 62

    Article  CAS  Google Scholar 

  16. Wagner F B, Nielsen P B, Boe-Hansen R and Albrechtsen H J 2016 Copper deficiency can limit nitrification in biological rapid sand filters for drinking water production Water Res. 95 280

    Article  CAS  Google Scholar 

  17. Seo H, An M, Kim B Y, Choi J H, Helal A and Kim H S 2017 Highly selective fluorescent probe for sequential recognition of copper (II) and iodide ions Tetrahedron 73 4684

  18. Mahapatra A K, Mondal S, Manna S K, Maiti K, Maji R, Uddin, M R and Maiti D K 2015 A new selective chromogenic and turn-on fluorogenic probe for copper (II) in solution and vero cells: recognition of sulphide by [CuL] Dalton Trans. 44 6490

  19. Erdemir S and Malkondu S 2015 Novel “turn on” fluorescent sensors based on anthracene and carbazone units for Cu (II) ion in CH3CN–H2O J. Lumin. 158 86

    Article  CAS  Google Scholar 

  20. You G R, Park G J, Lee J J and Kim C 2015 A colorimetric sensor for the sequential detection of Cu2+ and CN− in fully aqueous media: practical performance of Cu2+ Dalton Trans. 44 9120

  21. Na Y J, Choi Y W, Yun J Y, Park K M, Chang P S and Kim C 2015 Dual-channel detection of Cu2+ and F− with a simple Schiff-based colorimetric and fluorescent sensor Spectrochim. Acta A Mol. Biomol. Spectrosc. 136 1649

    Article  CAS  Google Scholar 

  22. Zhang X, Shen L Y, Zhang Q L, Yang X J, Huang Y L, Redshaw C and Xu H 2021 A simple turn-off Schiff base fluorescent sensor for copper (II) ion and its application in water analysis Molecules 26 1233

  23. Kumar J, Bhattacharyya P K and Das D K 2015 New duel fluorescent “on–off” and colorimetric sensor for Copper (II): Copper (II) binds through N coordination and pi cation interaction to sensor Spectrochim. Acta A Mol. Biomol. Spectrosc. 138 99

    Article  CAS  Google Scholar 

  24. St John P C, Guan Y, Kim Y, Kim S and Paton R S 2020 Prediction of organic homolytic bond dissociation enthalpies at near chemical accuracy with sub-second computational cost Nat. Commun. 11 1

    Article  Google Scholar 

  25. Ghammamy S and Sohrabi N 2013 Structural Properties, Natural Bond Orbital, Theory Functional Calculations (DFT), and Energies for the C13H10N4O2S Compounds Asian J. Chem. 6 114

    Google Scholar 

  26. Buevich A V and Elyashberg M E 2020 Enhancing computer-assisted structure elucidation with DFT analysis of J-couplings Magn. Reson. Chem. 58 594

    Article  CAS  Google Scholar 

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Acknowledgements

The Authors are thankful to the Department of Science and Technology, Govt. of India, and the Director of the Institute of Advanced Study in Science and Technology.

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Authors and Affiliations

  1. Environmental Chemistry Laboratory, Resource Management and Environmental Section, Life Sciences Division, Institute of Advanced Study in Science and Technology (IASST), Guwahati, Assam, 781035, India

    Bhaswati Devi & Arundhuti Devi

  2. Department of Chemistry, Cotton University, Guwahati, Assam, 781001, India

    Ankur Kanti Guha

  3. Environmental Biotechnology Laboratory, Resource Management and Environmental Section, Life Sciences Division, Institute of Advanced Study in Science and Technology, Guwahati, Assam, 781035, India

    Chandana Malakar

Authors
  1. Bhaswati Devi
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  2. Ankur Kanti Guha
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  3. Chandana Malakar
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  4. Arundhuti Devi
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Contributions

Bhaswati Devi: Conceived the idea of sensing Cu2+ ions in water by a synthetically prepared Schiff base fluorescent sensor, which is also feasible as a potential antibacterial agent, data analysis, and manuscript preparation. Dr. Ankur Kanti Guha: Performed the DFT calculation study and manuscript preparation. Chandana Malakar: Manuscript preparation. Dr. Arundhuti Devi: Supervision and manuscript preparation.

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Correspondence to Arundhuti Devi.

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The authors declare that they have no known competing financial interests or personal relationships that could have appeared to influence the work reported in this manuscript.

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Devi, B., Guha, A.K., Malakar, C. et al. Synthesis, characterization, Density Functional Theory (DFT) calculation, and fluorescent study of an efficient and novel Schiff base Cu(II) sensor. J Chem Sci 134, 88 (2022). https://doi.org/10.1007/s12039-022-02083-9

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  • DOI: https://doi.org/10.1007/s12039-022-02083-9

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