Skip to main content
SpringerLink
Log in

“Turn-on” fluorescent and colorimetric determination of Cu2+ ions in aqueous media based on a Rhodamine-N-phenyl Semicarbazide derivative

  • Published:
Fibers and Polymers Aims and scope Submit manuscript

Abstract

We report the design and synthesis of a novel chemosensor (RGPS) rhodamine-based indicator for selective detection of Cu2+ ion. Sensing behavior toward various metal ions (M=Hg2+, Cu2+, Co2+, K+, Cs+, Ag+, Pb2+, Zn2+, Mg2+, Fe3+, Ni2+, Li+ and Al3+) was investigated by UV-Vis and fluorescence spectroscopy in acetonitrile:water (CH3CN-H2O, v/v, 9:1) solution. The indicator exhibited highly selective and sensitive colorimetric and “turn-on” fluorescent responses toward Cu2+ ions based on the ring-opening mechanism of the rhodamine spirolactam in an CH3CN-H2O (v/v, 9:1) solution. The obvious change from colorless to pale pink upon the addition of Cu2+ could make it a suitable “naked eye” indicator for Cu2+. More significantly, the sensor displayed a remarkable colorless to yellowish green fluorescence switch in the presence of Cu2+ ions. The limit of detection is proved 1.405×10−7 M from titration and 1:1 binding ratio is proved from jobs plot method. Finally, we proposed a reversible ring-opening mechanism (OFF-ON) of the rhodamine spirolactam induced by Cu2+ binding and forming a 1:1 stoichiometric complex of RGPS-Cu2+ which is supported by the material studio theory calculations.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. A. L. Sommer, Plant Physiol., 6, 339 (1931).

    Article  CAS  Google Scholar 

  2. U. Ricardo, O. Manuel, and G. Mauricio, Am. J. Clin. Nutr., 67, 9525 (1998).

    Google Scholar 

  3. E. J. Underwood in “Copper in Trace Elements in Humans and Animals Nutrition”, 4th ed. (E. J. Underwood), pp.56–233, Academic Press New York, 1971.

    Google Scholar 

  4. R. R. Crichton, D. T. Dexter, and R. J. Warc, Coord. Chem. Rev., 252, pp252–1189 (2008).

    Article  CAS  Google Scholar 

  5. S. Adrian in “US Environmental Protection Agency”, Washington, DC, USA, 1996.

  6. S. Kousar and M. Javed, Int. J. Agric. Biol., 14, 801 (2012).

    CAS  Google Scholar 

  7. T. Gomes, C. G. Pereira, C. Cardoso, J. P. Pinheiro, I. Cancioand, M. J. BebianAquat.Toxicol., 72, 118 (2012)

    Google Scholar 

  8. E. J. Jun, H. N. Won, J. S. Kim, K. H. Lee, and J. Yoon, Tetrahedron Lett., 47, 4577 (2006).

    Article  CAS  Google Scholar 

  9. Z. Xu, J. Yoon, and D. R. Spring, Chem. Commun., 46, 2563 (2010).

    Article  CAS  Google Scholar 

  10. Z. Xu, J. Pan, D. R. Spring, J. Cui, and J. Yoon, Tetrahedron, 66, 1678 (2010).

    Article  CAS  Google Scholar 

  11. J. H. Jung, M. H. Lee, H. J. Kim, H. S. Jung, S. Y. Lee, N. R. Shin, K. No, and J. S. Kim, Tetrahedron Lett., 50, 2013 (2009).

    Article  CAS  Google Scholar 

  12. D. Maity, D. Karthigeyan, T. K. Kundu, and T. Govindaraju, Sens. Actuator B-Chem., 176, 831 (2013).

    Article  CAS  Google Scholar 

  13. T. W. Lin and S. D. Huang, Anal. Chem., 73, 4319 (2001).

    Article  CAS  Google Scholar 

  14. N. Pourreza and R. Hoveizavi, Anal. Chim. Acta, 549, 124 (2005).

    Article  CAS  Google Scholar 

  15. Y. Lin, P. Liang, and L. Guo, Talanta, 68, 25 (2005).

    Article  Google Scholar 

  16. J. S. Becker, M. V. Zoriy, C. Pickhardt, G. N. Palomer, and K. Zilles, Anal. Chem., 77, 3208 (2005).

    Article  CAS  Google Scholar 

  17. L. Shi, C. Jing, W. Ma, D. W. Li, J. E. Halls, F. Marken, and Y. T. Long, Angew. Chem.-Int. Edit., 125, 6127 (2013).

    Article  Google Scholar 

  18. T. Shtoyko, S. Conklin, A. T. Maghasi, J. N. Richardson, A. Piruska, C. J. Seliskar, and W. R. Heineman, Anal. Chem., 76, 1466 (2004).

    Article  CAS  Google Scholar 

  19. A. A. Ensafi, T. Khayamiam, A. Benvidi, and E. Mirmomtaz, Anal. Chim. Acta, 251, 225 (2006).

    Article  Google Scholar 

  20. K. P. Prathish, D. James, J. Jaisy, and T. P. Rao, Anal. Chim. Acta, 647, 84 (2009).

    Article  CAS  Google Scholar 

  21. S. Bhattachaya and M. Thomas, Tetrahedron Lett., 41, 10313 (2000).

    Article  Google Scholar 

  22. X. B. Zhang, J. Peng, C. L. He, G. L. Shen, and R. Q. Yu, Anal. Chim. Acta, 567, 189 (2006).

    Article  CAS  Google Scholar 

  23. O. Oter, K. Ertekin, C. Kirilmis, and M. Koca, Anal. Chim. Acta, 584, 308 (2007).

    Article  CAS  Google Scholar 

  24. Y. K. Jang, U. C. Nam, H. L. Kwon, I. H. Hwang, and C. Kim, Dyes Pigment., 99, 6 (2013).

    Article  CAS  Google Scholar 

  25. C. X. Yin, L. J. Qua, and F. J. Huo, Chinese Chem. Lett., 25, 1230 (2014).

    Article  CAS  Google Scholar 

  26. N. Aksuner, E. Henden, I. Yilmaz, and A. Cukurovali, Dyes Pigment., 83, 217 (2009).

    Article  Google Scholar 

  27. L. Zhang, J. Fan, and X. Peng, Spectrochim. Acta A, 73, 398 (2009).

    Article  Google Scholar 

  28. X. Chen, T. Pradhan, F. Wang, J. S. Kim, and J. Yoon, Chem. Rev., 112, 1910 (2012).

    Article  CAS  Google Scholar 

  29. D. T. Quang, J. S. Wu, N. D. Luyen, T. Duong, N. D. Dan, N. C. Bao, and P. T. Quy, Spectrochim. Acta A, 78, 753 (2011).

    Article  Google Scholar 

  30. V. B. Bojinov, A. I. Venkova, and N. I. Georgiev, Sens. Actuator B-Chem., 143, 42 (2009).

    Article  Google Scholar 

  31. L. F. Zhang, J. L. Zhao, X. Zeng, L. Mu, X. K. Jiang, M. Deng, J. X. Zhang, and G. Wei, Sens. Actuator B-Chem., 160, 662 (2011).

    Article  CAS  Google Scholar 

  32. Y. Ma, X. Zhang, Z. Guan, Y. Cao, and J. Yao, J. Mater. Res., 16, 2928 (2001).

    Article  CAS  Google Scholar 

  33. D. Maity, D. Karthigeyan, T. K. Kundu, and T. Govindaraju, Sens. Actuator B-Chem., 176, 831 (2013).

    Article  CAS  Google Scholar 

  34. S. Y. Lee, H. J. Kim, J. S. Wu, K. No, and J. S. Kim, Tetrahedron Lett., 49, 6141 (2008).

    Article  CAS  Google Scholar 

  35. Z. Xu, L. Zhang, R. Guo, T. Xiang, C. Wu, Z. Zhang, and F. Yang, Sens. Actuator B-Chem., 156, 546 (2011).

    Article  CAS  Google Scholar 

  36. K. M. K. Swamy, S. K. Ko, S. K. Kwon, H. N. Lee, C. Mao, J. M. Kim, K. H. Lee, J. Kim, I. Shin, and J. Yoon, Chem. Commun., 5915 (2008).

    Google Scholar 

  37. J. F. Zhang, Y. Zhou, J. Yoon, Y. Kim, S. J. Kim, and S. H. Kim, Org. Lett., 12, 3852 (2010).

    Article  CAS  Google Scholar 

  38. Z. Yang, M. She, J. Zhang, X. Chen, Y. Huang, H. Zhu, P. Liu, J. Li, and Z. Shi, Sens. Actuator B-Chem., 176, 482 (2013).

    Article  CAS  Google Scholar 

  39. F. Huo, L. Wang, C. Yin, Y. Yang, H. Tong, J. Chao, and Y. Zhang, Sens. Actuator B-Chem., 188, 735 (2013).

    Article  CAS  Google Scholar 

  40. A. R. Boddu, H. Kim, and Y. A. Son, Sens. Actuator BChem., 188, 847 (2013).

    Article  Google Scholar 

  41. S. H. Lee, A. R. Boddu, and Y. A. Son, Sens. Actuator BChem., 196, 388 (2014).

    Article  CAS  Google Scholar 

  42. H. S. So, A. R. Boddu, J. Hwang, K. Yesudas, and Y. A. Son, Sens. Actuator B-Chem., 202, 779 (2014).

    Article  CAS  Google Scholar 

  43. H. Kim, S. H. Kim, D. H. Lee, and Y. A. Son, Supramol. Chem., 25, 87 (2013).

    Article  CAS  Google Scholar 

  44. J. W. Jeong, A. R. Boddu, and Y. A. Son, Sens. Actuator BChem., 208, 75 (2015).

    Article  CAS  Google Scholar 

  45. H. Kim, A. R. Boddu, J. W. Jeong, S. Mallick, S. M. Kang, J. S. Choi, C. S. Lee, Y. A. Son, Sens. Actuator B-Chem. (2015), DOI: http://dx.doi.org/doi: 10.1016/j.snb.2014.12.100.

    Google Scholar 

  46. S. H. Lee, A. R. Boddu, and Y. A. Son, Sens. Actuator BChem. (2015), DOI: http://dx.doi.org/doi:10.1016/j.snb.2015. 01.008.

    Google Scholar 

  47. Y. A. Son and J. Park, Textile Color. Finish., 24, 158 (2012).

    Article  Google Scholar 

  48. A. R. Boddu, J. Y. Lee, and Y. A. Son, Supramol. Chem., 27, 191 (2015).

    Article  Google Scholar 

  49. A. R. Boddu, J. Y. Lee, and Y. A. Son, Spectrochim. Acta A, 127, 268 (2014).

    Article  Google Scholar 

  50. H. Kim, A. R. Boddu, and Y. A. Son, Fiber. Polym., 14, 2010 (2013).

    Article  CAS  Google Scholar 

  51. E. M. Lee, S. Y. Gwon, Y. A. Son, and S. H. Kim, Spectrochim. Acta A, 95, 25 (2012).

    Article  CAS  Google Scholar 

  52. M. W. Beukers, M. J. Wanner, J. K. V. F. Drabbe Kunzel, E. C. Klaasse, A. P. IJzerman, and G.-J. Koomen, J. Med. Chem., 46, 1492 (2003).

    Article  CAS  Google Scholar 

  53. Z. Zhang, Y. Zheng, W. Hang, X. Yan, and Y. Zhao, Talanta, 85, 779 (2011).

    Article  CAS  Google Scholar 

  54. H. Li, J. Fan, F. Song, H. Zhu, J. Du, S. Sun, and X. Peng, Chem. Eur. J., 16, 12349 (2010).

    Article  CAS  Google Scholar 

  55. P. MacCarthy, Anal. Chem., 50, 2165 (1978).

    Article  CAS  Google Scholar 

  56. Y. Zhou, F. Wang, Y. M. Kim, S. J. Kim, and J. Y. Yoon, Org. Lett., 11, 4442 (2009).

    Article  CAS  Google Scholar 

  57. B. Delley, J. Chem. Phys., 92, 508 (1990).

    Article  CAS  Google Scholar 

  58. B. Delley, J. Chem. Phys., 113, 7756 (2000).

    Article  CAS  Google Scholar 

  59. A. D. Boese and N. C. Handy, J. Chem. Phys., 114, 5497 (2001).

    Article  CAS  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Advanced Organic Materials and Textile System Engineering, Chungnam National University, Daejeon, 305-764, Korea

    Boddu Ananda Rao & Young-A Son

  2. Graduate School of Energy Science and Technology, Chungnam National University, Daejeon, 305-764, Korea

    Junemin Park

Authors
  1. Junemin Park
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Boddu Ananda Rao
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Young-A Son
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Young-A Son.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Park, J., Rao, B.A. & Son, YA. “Turn-on” fluorescent and colorimetric determination of Cu2+ ions in aqueous media based on a Rhodamine-N-phenyl Semicarbazide derivative. Fibers Polym 16, 953–960 (2015). https://doi.org/10.1007/s12221-015-0953-5

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s12221-015-0953-5

Keywords

Search

Navigation