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A naked-eye fluorescent sensor for copper(II) ions based on a naphthalene conjugate Bodipy dye

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Abstract

A novel naphthalene-Bodipy dye (N-Bodipy) was designed, prepared and characterized. N-Bodipy showed a selective and sensitive recognition toward Cu(II) ions as a fluorescent antenna group in aceto-nitrile/water over other metal cations. The complexation between Cu(II) ions and N-Bodipy gave a specific color change as well as caused fluorescence quenching under long-wavelength light (365 nm). The remarkable quenching effect in fluorescence intensity centered at 538 nm was only observed in the presence of copper(II) ions. Moreover, the orange color of N-Bodipy solution turned pale-yellow depending on the complexation effect in daylight. The complex stoichiometry was determined using a Job's plot and it was found to be 2: 1 (ligand/metal). The binding constant was calculated with the Benesi-Hildebrand equation to be 1.39 x 1010 M−1 and the detection limit was 1.28 μM (LOD = 3α/slope, α is the standard deviation) for Cu(II). The data proved that the binding between N-Bodipy and Cu(II) is chemically reversible.

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References

  1. K. Mariappan, M. Alaparthi, G. Caple, V. Balasubramanian, M. M. Hoffman, M. Hudspeth and A. G. Sykes, Selective Fluorescence Sensing of Copper(II) and Water via Competing Imine Hydrolysis and Alcohol Oxidation Pathways Sensitive to Water Content in Aqueous Acetonitrile Mixtures, Inorg. Chem., 2014, 53, 2953–2962.

    Article  CAS  Google Scholar 

  2. C. Y. Chou, S. R. Liu and S. P. Wu, A highly selective turn-on fluorescent sensor for Cu(II) based on an NSe2 chelating moiety and its application in living cell imaging, Analyst, 2013, 138, 3264–3270.

    Article  CAS  Google Scholar 

  3. EPA National Primary Drinking Water Regulations, http://water.epa.gov/drink/contaminants/index.cfm#1 (accessed Dec 4, 2012).

  4. A. P. S. Gonzales, M. A. Firmino, C. S. Nomura, F. R. P. Rocha, P. V. Oliveira and I. Gaubeur, Peat as a natural solid-phase for copper preconcentration and deter-mination in a multicommuted flow system coupled to flame atomic absorption spectrometry, Anal. Chim. Acta, 2009, 636, 198–204.

    Article  CAS  Google Scholar 

  5. C. Shi, S. Xie and J. Jia, The Study of a New Method to Determine Copper Ion by Square-Wave Voltammetry-Extraction Iodometry at the Liquid/Liquid Interfaces, J. Autom. Methods Manage. Chem., 2008, 2008, 453429–453433.

    Article  Google Scholar 

  6. Y. Liu, P. Liang and L. Guo, Nanometer titanium dioxide immobilized on silica gel as sorbent for preconcentration of metal ions prior to their determination by inductively coupled plasma atomic emission spectrometry, Talanta, 2005, 68, 25–30.

    Article  CAS  Google Scholar 

  7. J. Zhanga, B. Zhaoa, C. Lia, X. Zhub and R. Qiao, A BODIPY-based “turn-on” fluorescent and colorimetric sensor forselective detection of Cu2+ in aqueous media and its application in cell imaging, Sens. Actuators. B, 2014, 196, 117–122.

    Article  Google Scholar 

  8. P. Anzenbacher, P. Lubal, P. Bucek, M. A. Palacios and M. E. Kozelkova, A practical approach to optical cross-reac-tive sensor arrays, Chem. Soc. Rev., 2010, 39, 3954–3979.

    Article  CAS  Google Scholar 

  9. T. C. Pearce, S. S. Schiffman, H. T. Nagle and J. W. Gardner, Handbook of Machine Olfaction: Electronic Nose Technology, Wiley-VCH Verlag Gmbh & Co, KGaA, Weinheim, 2003.

    Google Scholar 

  10. O. R. Mi-randa, H. T. Chen, C. C. You, D. E. Mortenson, X. C. Yang, U. H. F. Bunz and V. M. Rotello, Enzyme-Amplified Array Sensing of Proteins in Solution and in Biofluids, J. Am. Chem. Soc., 2010, 132, 5285–5289.

    Article  CAS  Google Scholar 

  11. N. S. Lewis, Comparisons between Mammalian and Artificial Olfaction Based on Arrays of Carbon Black-Polymer Composite Vapor Detectors, Acc. Chem. Res., 2004, 37, 663–672.

    Article  CAS  Google Scholar 

  12. F. Rock, N. Barsan and U. Weimar, Electronic nose: Current status and future trends, Chem. Rev., 2008, 108, 705–725.

    Article  Google Scholar 

  13. A. T. Wright and E. V. Anslyn, Differential receptor arrays and assays for solution-based molecular recognition, Chem. Soc. Rev., 2006, 35, 14–28.

    Article  CAS  Google Scholar 

  14. Y. Wu, N. Na, S. Zhang, X. Wang, D. Liu and X. Zhang, Discrimination and identification of flavors with catalytic nanomaterial-based optical chemosensor array, Anal. Chem., 2009, 81, 961–966.

    Article  CAS  Google Scholar 

  15. S. H. Lim, L. Feng, J. W. Kemling, C. J. Musto and K. S. Suslick, An Optoelectronic Nose for Detection of Toxic Gases, Nat. Chem., 2009, 1, 562–567.

    Article  CAS  Google Scholar 

  16. L. Feng, C. J. Musto and K. S. Suslick, A Simple and Highly Sensitive Colorimetric Detection Method for Gaseous Formaldehyde, J. Am. Chem. Soc., 2010, 132, 4046–4047.

    Article  CAS  Google Scholar 

  17. G. F. Nordberg, B. A. Fowler, M. Nordberg and L. Friberg, in Handbook on the Toxicology of Metals, Academic Press, Burlington, MA, 3rd edn, 2007.

    Google Scholar 

  18. P. Pohl, Determination of metal content in honey by atomic absorption and emission spectrometries, TrAC, Trends Anal. Chem., 2009, 28, 117–128.

    Article  CAS  Google Scholar 

  19. D. T. Quang and J. S. Kim, Fluoro-and chromogenic chemo-dosimeters for heavy metal ion detection in solution and biospecimens, Chem. Rev., 2010, 110, 6280–6301.

    Article  CAS  Google Scholar 

  20. B. Valeur, Molecular Fluorescence: Principles and Applications, Wiley-VCH, Weinheim, Germany, 2001.

    Book  Google Scholar 

  21. C. Chen, R. Wang, L. Guo, N. Fu, H. Dong and Y. Yuan, A squaraine-based colorimetric and “turn on” fluorescent sensor for selective detection of Hg2+ in an aqueous medium, Org. Lett., 2011, 13, 1162–1165.

    Article  CAS  Google Scholar 

  22. N. Dorh, S. Zhu, K. B. Dhungana, R. Pati, F. T. Luo, H. Liu and A. Tiwari, BODIPY-Based Fluorescent Probes for Sensing Protein Surface-Hydrophobicity, Sci. Rep., 2015, 5, 18337

    Article  CAS  Google Scholar 

  23. B. Taner, A. N. Kursunlu and E. Güler, Spectrochim. Acta, Part A, 2014, 118, 903–907

    Article  CAS  Google Scholar 

  24. A. N. Kursunlu, E. Guler, H. I. Ucan and R. W. Boyle, Dyes Pigm., 2012, 94(3), 496–502

    Article  CAS  Google Scholar 

  25. M. Bayrakci, A. N. Kursunlu, E. Güler and S. Ertul, Dyes Pigm., 2013, 99(2), 268–274

    Article  CAS  Google Scholar 

  26. A. N. Kursunlu, Z. E. Koc, A. Y. Obali and E. Güler, J. Lumin., 2014, 149, 215–220.

    Article  CAS  Google Scholar 

  27. Y. Lv, W. Wei and Y. Xie, Bodipy-Phenol-Based Sensor For Selectively Recognizing Three Basic Anions, J. Chil. Chem. Soc., 2015, 60, 2843–2846

    Article  Google Scholar 

  28. M. Formica, V. Fusi, L. Giorgi and M. Micheloni, New fluorescent chemosensors for metal ions in solution, Coord. Chem. Rev., 2012, 256, 170

    Article  CAS  Google Scholar 

  29. P. Hadi, P. Gao, J. P. Barford and G. Mckay, J. Hazard. Mater., 2013, 252-253, 166–170

    Article  Google Scholar 

  30. G. Ambrosi, E. Borgogelli, M. Formica, V. Fusi, L. Giorgi, M. Micheloni, E. Rampazzo, M. Sgarzi, N. Zaccheroni and L. Prodi, PluS Nanoparticles as a tool to control the metal complex stoi-chiometry of a new thio-aza macrocyclic chemosensor for Ag(I) and Hg(II) in water, Sens. Actuators, B, 2015, 207, 1035.

    Article  CAS  Google Scholar 

  31. J. Zhang, B. Zhao, C. Lia, X. Zhu and R. Qiao, A BODIPY-based “turn-on” fluorescent and colorimetric sensor forse-lective detection of Cu2+ in aqueous media and its appli-cation in cellimaging, Sens. Actuators, B, 2014, 196, 117–122.

    Article  CAS  Google Scholar 

  32. X. Liu, X. Yang, H. Peng, C. Zhu and Y. Cheng, A fluo-rescent sensor for Hg2+ and Ag+ functions as a molecular switch based on click-generated triazole moiety, Tetrahedron Lett., 2011, 52, 2295–2298.

    Article  CAS  Google Scholar 

  33. X. Liu, X. Yang, Y. Fu, C. Zhu and Y. Cheng, Novel fluo-rescent sensor for Ag+ and Hg2+ based on the BINOL-pyrene derivative via click reaction, Tetrahedron, 2011, 67, 3181–3186.

    Article  CAS  Google Scholar 

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Acknowledgements

We thank the Research Foundation of the Selcuk University (BAP) for financial support of this work (under project number: 15401013). The authors express their appreciation to Prof. Dr Ersin Güler for helpful discussions.

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Correspondence to Ahmed Nuri Kursunlu.

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Baslak, C., Kursunlu, A.N. A naked-eye fluorescent sensor for copper(II) ions based on a naphthalene conjugate Bodipy dye. Photochem Photobiol Sci 17, 1091–1097 (2018). https://doi.org/10.1039/c8pp00137e

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  • DOI: https://doi.org/10.1039/c8pp00137e

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