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A new biphenylcarbonitrile based fluorescent sensor for Zn2+ ions and application in living cells

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Abstract

A new and efficient fluorescent sensor 4′-hydroxy-3′-[(4-antipyrineimino)methyl]-4-biphenylcarboni- trile(L) was prepared for the selective detection of Zn2+ in aqueous ethanol medium. When excited at 419 nm, the fluorescent intensity of sensor L at 507 nm was remarkably increased more than 54-fold after adding Zn2+ ions. The strong green emission of the solution can be easily identified by naked eye under UV light. Thus, sensor L behaves as a naked eye fluorescent “turn on” detector for Zn2+ ions. The fluorescence enhancement might be attributed to the inhibition of excited state intramolecular proton transfer(ESIPT) and C=N isomerization as well as the chelation enhanced fluorescence(CHEF) effect. The complex solution of sensor L with Zn2+ ions exhibited reversibility with ethylene diamine tetraacetic acid(EDTA) and the probe could be recycled for further use. Notably, sensor L could clearly distinguish Zn2+ from Cd2+. The interaction of sensor L with zinc ions was investigated by means of FTIR, 1H NMR and HRMS spectroscopy. Furthermore, sensor L has been applied for cell imaging studies.

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References

  1. Patra C., Bhanja A. K., Sen C., Ojha D., Chattopadhyay D., Mahapa-traa A., Sinha C., RSC Adv., 2016, 6, 53378

    Article  CAS  Google Scholar 

  2. Tsvetkov P. O., Popov I. A., Nikolaev E. N., Archakov A. I., Makarov A. A., Kozin S. A., Chem. Bio. Chem., 2008, 9, 1564

    Article  CAS  Google Scholar 

  3. Kapur J., Macdonald R. L., J. Neurosci., 1997, 17, 7532

    CAS  Google Scholar 

  4. Wei G., Hough C. J., Li Y., Sarvey J. M., Neurosci., 2004, 125, 867

    Article  CAS  Google Scholar 

  5. Mertens J., Degryse F., Springael D., Smolders E., Environ. Sci. Technol., 2007, 41, 2992

    Article  CAS  Google Scholar 

  6. Li L., Du L. T., Sun J., Yan C. G., Chem. Res. Chinese Universities, 2013, 29(5), 874

    Article  CAS  Google Scholar 

  7. Xu Z. C., Yoon J., Spring D. R., Chem. Soc. Rev., 2010, 39, 1996

    Article  CAS  Google Scholar 

  8. Li J. F., Yin C. X., Huo F. J., Dyes Pigments, 2016, 131, 100

    Article  CAS  Google Scholar 

  9. Tayade K., Sahoo S. K., Bondhopadhyay B., Bhardwaj V. K., Singh N., Basu A., Bendrea R., Kuwar A., Biosens. Bioelectron., 2014, 61, 429

    Article  CAS  Google Scholar 

  10. Zhang T. T., Chen X. P., Liu J. T., Zhang L. Z., Chu J. M., Su L., Zhao B. X., RSC Adv., 2014, 4, 16973

    Article  CAS  Google Scholar 

  11. Fuentes P. R., Lippard S. J., Chem. Med. Chem., 2014, 9, 1238

    Article  Google Scholar 

  12. Tang L. J., Dai X., Zhong K. L., Wu D., Wen X., Sens. Actuators B, 2014, 203, 557

    Article  CAS  Google Scholar 

  13. Datta B. K., Thiyagarajan D., Samanta S., Ramesh A., Das G., Org. Biomol. Chem., 2014, 12, 4975

    Article  CAS  Google Scholar 

  14. Wang J. F., Li Y. B., Duah E., Paruchuri S., Zhou D. M., Pang Y., J. Mater. Chem. B, 2014, 2, 2008

    Article  CAS  Google Scholar 

  15. Tang L. J., Cai M. J., Zhou P., Zhao J., Huang Z. L., Zhong K. L., Hou S. H., J. Lumin., 2014, 147, 179

    Article  CAS  Google Scholar 

  16. Borthakur R., Thapa U., Asthana M., Mitra S., Ismail K., Lal R. A., J. Photochem. Photobiol. A Chem., 2015, 301, 6

    Article  CAS  Google Scholar 

  17. Mandal S., Sikdar Y., Maiti D. K., Maiti G. P., Mandal S. K., Biswas J. K., Goswami S., RSC Adv., 2015, 5, 72659

    Article  CAS  Google Scholar 

  18. Lee S. K., Choi M. G., Choi J., Chang S. K., Sens. Actuators B, 2015, 207, 303

    Article  CAS  Google Scholar 

  19. Hagimori M., Mizuyama N., Tominaga Y., Mukai T., Saji H., Dyes Pigments, 2015, 113, 205

    Article  CAS  Google Scholar 

  20. Wang X. C., Ma H. Y., Ding G., Lu Y., Gong Y. L., Zhang S. T., Luo Z. P., Li H. R., Gao F., Tetrahedron Lett., 2015, 56, 2758

    Article  CAS  Google Scholar 

  21. Kumari B., Lohar S., Ghosh M., Ta S., Sengupta A., Banerjee P. P., Chattopadhyay A., Das D., J. Fluoresc., 2016, 26, 87

    Article  CAS  Google Scholar 

  22. Li W., Tian X. H., Huang B., Li H. J., Zhao X. Y., Gao S., Zheng J., Zhang X. Z., Zhou H. P., Tian Y. P., Wu J. Y., Biosens. Bioelectron., 2016, 77, 530

    Article  CAS  Google Scholar 

  23. Pawar S., Akula M., Labala S., Venuganti V. V. K., Bhattacharya A., Nag A., Chem. Plus. Chem., 2016, 81, 1339

    CAS  Google Scholar 

  24. Findik M., Ucar A., Bingol H., Guler E., Ozcan E., Res. Chem. In-termed., 2017, 43, 401

    CAS  Google Scholar 

  25. Dey S., Roy A., Maiti G. P., Mandal S. K., Banerjeea P., Roy P., New J. Chem., 2016, 40, 1365

    Article  CAS  Google Scholar 

  26. Naskar B., Modark R., Sikdar Y., Maiti D. K., Banik A., Dangar T. K., Mukhopadhyay S., Mandal D., Goswami S., J. Photochem. Photobiol. A Chem., 2016, 321, 99

    Article  CAS  Google Scholar 

  27. Patra C., Bhanja A. K., Sen C., Ojha D., Chattopadhyay D., Mahapa-tra A., Sinha C., Sens. Actuators B, 2016, 228, 287

    Article  CAS  Google Scholar 

  28. Ponnuvel K., Kumar M., Padmini V., Sens. Actuators B, 2016, 227, 242

    Article  CAS  Google Scholar 

  29. Xiao S. H., Liu Z., Zhao J. Y., Pei M. S., Zhang G. Y., He W., RSC Adv., 2016, 6, 27119

    Article  CAS  Google Scholar 

  30. Saini A. K., Srivastava M., Sharma V., Mishra V., Mobin S. M., Dal-ton Trans., 2016, 45, 3927

    Article  CAS  Google Scholar 

  31. Li Y. Y., Li K., He J., Talanta, 2016, 153, 381

    Article  CAS  Google Scholar 

  32. Yan J., Fan L., Qin J. C., Li C. R., Yang Z. Y., Tetrahedron Lett., 2016, 57, 2910

    Article  CAS  Google Scholar 

  33. Choi Y. W., You G. R., Lee J. J., Kim C., Inorg. Chem. Commun., 2016, 63, 35

    Article  CAS  Google Scholar 

  34. Lin H. Y., Chen T. Y., Liu C. K., Wu A. T., Luminescence, 2016, 31, 236

    Article  CAS  Google Scholar 

  35. Ge Y., Ma W., Li N. Y., Wang S. J., Liu D., Inorg. Chim. Acta, 2015, 432, 32

    Article  CAS  Google Scholar 

  36. Alici O., Erdemir S., Sens. Actuators B, 2015, 208, 159

    Article  CAS  Google Scholar 

  37. Sarkar D., Pramanik A. K., Mondal T. K., J. Lumin., 2014, 146, 480

    Article  CAS  Google Scholar 

  38. Wu Y. K., Peng X. J., Guo B. C., Fan J. L., Zhang Z. C., Wang J. Y., Cui A. J., Gao Y. L., Org. Biomol. Chem., 2015, 3, 1387

    Article  Google Scholar 

  39. Li P. X., Zhou X. Y., Huang R. Y., Yang L. Z., Tang X. L., Dou W., Zhou Q. Q., Liu W. S., Dalton Trans., 2014, 43, 706

    Article  CAS  Google Scholar 

  40. Roy N., Nath S., Dutta A., Mondal P., Paul P. C., Singh T. S., RSC Adv., 2016, 6, 63837

    Article  CAS  Google Scholar 

  41. Kumar Y. P., King P., Prasad V. S. R. K., Chem. Eng. J., 2016, 124, 63

    Article  Google Scholar 

  42. Pan Y., Shi Y. P., Chen J. Y., Wong C. M., Zhang H., Li M. J., Li C. W., Yi C. Q., Mater. Sci. Eng. C, 2016, 69, 561

    Article  CAS  Google Scholar 

  43. Schneider H. J., Yatsimirsky A. K., Principles and Methods in Supramolecular Chemistry, John Wiley, New York, 2000, 148

    Google Scholar 

  44. Benesi H. A., Hildebrand J. H., J. Am. Chem. Soc., 1949, 71, 2703

    Article  CAS  Google Scholar 

  45. Yang G. Q., Savary F. M., Peng Z. K., Wu S. K., Fouassier J. P., Chem. Phys. Lett., 1996, 256, 536

    Article  CAS  Google Scholar 

  46. Wu J. S., Liu W. M., Zhuang X. Q., Wang F., Wang P. F., Tao S. L., Zhang X. H., Wu S. K., Lee S. T., Org. Lett., 2007, 9, 33

    Article  CAS  Google Scholar 

  47. Xu Y., Pang Y., Dalton Trans., 2011, 40, 1503

    Article  CAS  Google Scholar 

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Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Shanxi University, Taiyuan, 030006, P. R. China

    Jia Feng, Xiuqing Shao, Zhuobin Shang, Jianbin Chao & Yu Wang

  2. College of Chemistry, Beijing Normal University, Beijing, 100875, P. R. China

    Weijun Jin

Authors
  1. Jia Feng
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  2. Xiuqing Shao
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  3. Zhuobin Shang
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  4. Jianbin Chao
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  5. Yu Wang
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  6. Weijun Jin
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Corresponding authors

Correspondence to Yu Wang or Weijun Jin.

Additional information

Supported by the Natural Science Foundation of Shanxi Province, China(No.2013011040-6), the Project Sponsored by the Scientific Research Foundation for the Returned Overseas Chinese Scholars, the Ministry of Education of China.

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Feng, J., Shao, X., Shang, Z. et al. A new biphenylcarbonitrile based fluorescent sensor for Zn2+ ions and application in living cells. Chem. Res. Chin. Univ. 33, 695–701 (2017). https://doi.org/10.1007/s40242-017-7084-z

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  • DOI: https://doi.org/10.1007/s40242-017-7084-z

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