Skip to main content
SpringerLink
Log in

Synthesis of Highly Sensitive Fluorescent Probe Based on Tetrasubstituted Imidazole and Its Application for Selective Detection of Ag+ Ion in Aqueous Media

  • Published:
Chemical Research in Chinese Universities Aims and scope

Abstract

A small molecule fluorescent probe, 4-[2-(4-chlorophenyl)-4,5-diphenyl-1H-imidazol-1-yl]aniline(L) for detecting Ag+ ion was gently synthesized via one-pot multi-component reaction catalyzed by H3[PW12O40] under solvent-free microwave irradiation. When the concentration of Ag+ ion changed from 0 to 8.0×10−6 mol/L in the solution of H2O/CH3OH(19:1, volume ratio), the fluorescence emission spectrum was blue-shifted and accompanied by a gradual increase in fluorescence intensity with a low detection limit of 3.0×10−11 mol/L. Moreover, UV-Vis absorption titration experiment demonstrated a 1:1 stoichiometric ratio and an association constant of (9.95±0.44)×105 L/mol between probe L and Ag+ ion, and thus their complexation mechanism was also proposed and verified. More importantly, this fluorescent probe was remarkably specific for Ag+ ion under the interference of other metal ions and exhibited a wide pH application range of 4.0―8.0. Additionally, preliminary application of this probe was also carried out and satisfactory results were shown.

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. Ye Z., Duan C., Sheng R., Xu J., Wang H., Zeng L., Talanta 2018, 176, 389

    Article  CAS  PubMed  Google Scholar 

  2. Zhao Q., Kang J., Wen Y., Huo F., Zhang Y., Yin C., Spectrochim. Acta A 2018, 189, 8

    Article  CAS  Google Scholar 

  3. Melaiye A., Sun Z., Hindi K., Milsted A., Ely D., Reneker D. H., Tessier C. A., Youngs W. J., J. Am. Chem. Soc., 2005, 127, 2285

    Article  CAS  PubMed  Google Scholar 

  4. Yang Y., Li W., Qi H., Zhang Q., Chen J., Wang Y., Wang B., Wang S., Yu C., Anal. Biochem. 2012, 430, 48

    Article  CAS  PubMed  Google Scholar 

  5. Xiang G., Cui W., Lin S., Wang L., Meier H., Li L., Cao D., Sensor Actuat. B: Chem. 2013, 186, 741

    Article  CAS  Google Scholar 

  6. Wang H., Zhu X., Xu H., Yuan Q., Sensor Actuat. B: Chem. 2017, 238, 985

    Article  CAS  Google Scholar 

  7. Li H. W., Yue Y., Liu T. Y., Li D., Wu Y., J. Phys. Chem. C, 2013, 117, 16159

    Article  CAS  Google Scholar 

  8. Lou X., Qiang L., Qin J., Li Z., ACS Appl. Mater. Inter., 2009, 1, 2529

    Article  CAS  Google Scholar 

  9. Wang H., Wang D., Wang Q., Li X., Schalley C. A., Org. Biomol. Chem. 2010, 8, 1017

    Article  CAS  PubMed  Google Scholar 

  10. Huo F. J., Yin C. X., Yang Y. T., Su J., Chao J. B., Liu D. S., Anal. Chem. 2012, 84, 2219

    Article  CAS  PubMed  Google Scholar 

  11. Shin D. H., Ko Y. G., Choi U. S., Kim W. N., Ind. Eng. Chem. Res. 2006, 45, 656

    Article  CAS  Google Scholar 

  12. Liu J., Lu Y., J. Am. Chem. Soc., 2007, 129, 9838

    Article  CAS  PubMed  Google Scholar 

  13. Mao J., Wang L., Dou W., Tang X., Yan Y., Liu W., Org. Lett. 2007, 9, 4567

    Article  CAS  PubMed  Google Scholar 

  14. Zhao Y., Zhang X. B., Han Z. X., Qiao L., Li C. Y., Jian L. X., Shen G. L., Yu R. Q., Anal. Chem. 2009, 81, 7022

    Article  CAS  PubMed  Google Scholar 

  15. Chen Y. Y., Lin H. C., Polymer 2007, 48, 5268

    Article  CAS  Google Scholar 

  16. Tan J. L., Zhang M. X., Zhang F., Yang T. T., Liu Y., Li Z. B., Zuo H., Spectrochim. Acta A 2015, 140, 489

    Article  CAS  Google Scholar 

  17. Bao Y., Li Q., Liu B., Du F., Tian J., Wang H., Wang Y., Bai R., Chem. Commun. 2012, 48, 118

    Article  CAS  Google Scholar 

  18. Dierschke F., Müllen K., Macromol. Chem. Phys. 2007, 208, 37

    Article  CAS  Google Scholar 

  19. Chen Y., Gu Q., Li B., Chen Q., Chen X., Zhang Y., Liu J., CR. Chim., 2013, 16, 1103

    Article  CAS  Google Scholar 

  20. Baghbanzadeh M., Carbone L., Cozzoli P. D., Kappe C. O., Angew. Chem. Int. Ed. 2011, 50, 11312

    Article  CAS  Google Scholar 

  21. Chen S. S., Cryst. Eng. Comm. 2016, 18, 6543

    Article  CAS  Google Scholar 

  22. Faridbod F., Sedaghat M., Hosseini M., Ganjali M. R., Khoobi M., Shafiee A., Norouzi P., Spectrochim. Acta A 2015, 137, 1231.

    Article  CAS  Google Scholar 

  23. Valeur B., Leray I., Coordin. Chem. Rev. 2000, 205, 3

    Article  CAS  Google Scholar 

  24. Liu B., Baudrey S., Jaeger L., Bazan G. C., J. Am. Chem. Soc., 2004, 126, 4076

    Article  CAS  PubMed  Google Scholar 

  25. Ho H. A., Leclerc M., J. Am. Chem. Soc., 2004, 126, 1384

    Article  CAS  PubMed  Google Scholar 

  26. Wen Y., Xing F., He S., Song S., Wang L., Long Y., Li D., Fan C., Chem. Commun. 2010, 46, 2596

    Article  CAS  Google Scholar 

  27. Askari M. S., Girard B., Murugesu M., Ottenwaelder X., Chem. Commun. 2011, 47, 8055

    Article  CAS  Google Scholar 

  28. Zhang X., Wang G., Spectrochim. Acta A 2009, 72, 1071

    Article  CAS  Google Scholar 

  29. Yang X. B., Yang B. X., Ge J. F., Xu Y. J., Xu Q. F., Liang J., Lu J. M., Org. Lett. 2011, 13, 2710

    Article  CAS  PubMed  Google Scholar 

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

    Article  CAS  Google Scholar 

  31. Zhu M., Yuan M., Liu X., Xu J., Lv J., Huang C., Liu H., Li Y., Wang S., Zhu D., Org. Lett. 2008, 10, 1481

    Article  CAS  PubMed  Google Scholar 

  32. Mirzaei M., Saeed J., Spectrochim. Acta A 2011, 82, 351

    Article  CAS  Google Scholar 

  33. Li C. Y., Xu F., Li Y. F., Spectrochim. Acta A 2010, 76, 197

    Article  CAS  Google Scholar 

  34. Mu H., Gong R., Ren L., Zhong C., Sun Y., Fu E., Spectrochim. Acta A 2008, 70, 923

    Article  CAS  Google Scholar 

Download references

Acknowledgements

We are grateful to Dr. WANG Chunyu(Jilin University) for NMR spectra test, Dr. WEI Zhonglin(Jilin University) for MS spectra test and Dr. DAO Jungang(Jilin University) for fluorescent emission spectra test.

Author information

Authors and Affiliations

  1. College of Chemistry, Jilin University, Changchun, 130012, P. R. China

    Zhiming Mi, Yao Chen, Xiaodong Chen, Liuqing Yan, Qiang Gu, Hanqi Zhang, Chunhai Chen & Yumin Zhang

Authors
  1. Zhiming Mi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Yao Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Xiaodong Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Liuqing Yan
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Qiang Gu
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Hanqi Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Chunhai Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. Yumin Zhang
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Yumin Zhang.

Electronic supplementary material

40242_2018_7426_MOESM1_ESM.pdf

Synthesis of highly sensitive fluorescent probe based on tetrasubstituted imidazole and its application for selective detection of Ag+ ion in aqueous media

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Mi, Z., Chen, Y., Chen, X. et al. Synthesis of Highly Sensitive Fluorescent Probe Based on Tetrasubstituted Imidazole and Its Application for Selective Detection of Ag+ Ion in Aqueous Media. Chem. Res. Chin. Univ. 34, 369–374 (2018). https://doi.org/10.1007/s40242-018-7426-5

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s40242-018-7426-5

Keywords

Search

Navigation