Skip to main content
SpringerLink
Log in

A Highly Selective Turn-On Fluorescent Chemosensor for Zinc Ion in Aqueous Media

  • ORIGINAL PAPER
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

In the paper, a novel rhodamine6G based fluorescent chemosensor bearing 3-carbaldehyde chromone was designed and synthesized. According to the fluorescence behavior toward several metal ions, it showed highly selectivity and sensitivity to Zn(II) over other commonly coexistent metal ions (Cu(II), Cd(II), Hg(II), Mg(II), K(I), Pb(II), Fe(III) and Cr(III)) in aqueous environment (pH = 7.4). Meanwhile the binding constant between Zn(II) and chemosensor achieved 6.21 × 1011 M−1 in aqueous media. Moreover, according to the Job plot, 1:1 stoichiometry between Zn(II) and sensor was deduced in aqueous media (pH = 7.4). The good selectivity and sensitivity in aqueous media effectively enhanced the application value of the fluorescent chemosensor for Zn(II).

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

Scheme 1
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8

Similar content being viewed by others

References

  1. Liu Y, Zhang SW, Miao Q, Zheng LF, Zong LL, Cheng YX (2007) Fluorescent chemosensory conjugated polymers based on optically active polybinaphthyls and 2,2′-bipyridyl units. Macromolecules 40:4839–4847

    Article  CAS  Google Scholar 

  2. Callan JF, de Silva AP, Magria DC (2005) Luminescent sensors and switches in the early 21st century. Tetrahedron 61:8551–8588

    Article  CAS  Google Scholar 

  3. Kim JS, Quang DT (2007) Calixarene-derived fluorescent probes. Chem Rev 107:3780–3799

    Article  PubMed  CAS  Google Scholar 

  4. Nolan EM, Lippard SJ (2009) Chemosensors for pyrophosphate. Acc Chem Res 42:23–31

    Article  Google Scholar 

  5. Clark MA, Duffy K, Tibrewala J, Lippard SJ (2003) Synthesis and metal-binding properties of chelating fluorescein derivatives. Org Lett 5:2051–2054

    Article  PubMed  CAS  Google Scholar 

  6. Wu DY, Huang W, Duan CY, Lin ZH, Meng QJ (2007) Highly sensitive fluorescent probe for selective detection of Hg2+ in DMF aqueous media. Inorg Chem 46:1538–1540

    Article  PubMed  CAS  Google Scholar 

  7. Wu JS, Hwang IC, Kim KS, Kim JS (2007) Rhodamine-based Hg2+-selective chemodosimeter in aqueous solution: fluorescent OFF-ON. Org Lett 9:907–910

    Article  PubMed  Google Scholar 

  8. Zhang JF, Zhou Y, Yoon JY, Kim YM, Kim JS (2010) Naphthalimide modified rhodamine derivate: ratiometric an selective fluorescent sensor for Cu2+ based on two different approaches. Org Lett 12:3852–3855

    Article  PubMed  CAS  Google Scholar 

  9. Chen XQ, Nam SW, Jou MJ, Kim YM, Kim SJ, Park SS, Yoon JY (2008) Hg2+ selective fluorescent and colorimetric sensor: its crystal structure and application to bioimaging. Org Lett 10:5235–5238

    Article  PubMed  CAS  Google Scholar 

  10. Yang YK, Cho HSJ, Lee JY, Shin IJ, Tae JS (2009) A rhodamine-hydroxamic acid-based fluorescent probe for hypochlorous acid and its applications to biological imagings. Org Lett 11:859–861

    Article  PubMed  CAS  Google Scholar 

  11. Vallee BL, Falchuk KH (1993) The biochemical basis of zinc physiology. Phys Rev 73:79–118

    Article  CAS  Google Scholar 

  12. Frederickson CJ, Koh J-Y, Bush AI (2005) The neurobiology of zinc in health and disease. Nat Rev Neurosci 6:449–462

    Article  PubMed  CAS  Google Scholar 

  13. Lippard SJ, Berg JM (1994) Principle of bioinogranic chemistry. University Science Book, CA, p 10, 14: 78–183

    Google Scholar 

  14. McRae R, Bagchi P, Sumalekshmy S, Fahrni CJ (2009) In situ imaging of metals in cells and tissues. Chem Rev 109:4780–4827

    Article  PubMed  CAS  Google Scholar 

  15. Voegelin A, Jacquat O, Pfister S, Barmettler K, Scheinost AC, Kretzschmar R (2011) Time-dependent changes of zinc speciation in four soils contaminated with zincite or sphalerite. Environ Sci Technol 45:255–261

    Article  PubMed  CAS  Google Scholar 

  16. Hisaindee S, Zahid O, Meetani MA, Graham J (2012) Fluorescent studies of salicylaldehyde and other related carbonyl compounds for the selective and sensitive detection of zinc(II) ions in aqueous solution. J Fluoresc 22:677–683

    Article  PubMed  CAS  Google Scholar 

  17. Lu XY, Zhu WH, Xie YS, Li X, Gao Y, Li FY, Tian H (2010) Near-IR core-substituted naphthalenediimide fluorescent chemosensors for zinc ions: ligand effect on PET and ICT channels. Chem Eur J 16:8355–8364

    Article  PubMed  CAS  Google Scholar 

  18. Xu Z, Baek K-H, Kim HN, Cui J, Qian X, Spring DR, Shin I, Yoon J (2010) Zn2+ triggered amide tautomerization produces a highly Zn2+ selective, cell-permeable and ratiometric fluorescent sensor. J Am Chem Soc 132:601–610

    Article  PubMed  CAS  Google Scholar 

  19. Zhou Y, You XY, Fang Y, Li JY, Liu K, Yao C (2010) A thiophen-thiooxorhodamine conjugate fluorescent probe for detecting mercury in aqueous media and living cells. Chem Commun 8:4819–4822

    CAS  Google Scholar 

  20. Buccella D, Horowitz JA, Lippard SJ (2011) Understanding zinc quantification with existing and advanced ditopic fluorescent Zinpyr sensors. J Am Chem Soc 133:4104–4114

    Article  Google Scholar 

  21. Yoon S, Albers AE, Wong AP, Chang CJ (2005) Screening mercury levels in fish with a selective fluorescent chemosensor. J Am Chem Soc 127:16030–16031

    Article  PubMed  CAS  Google Scholar 

  22. Zhou Y, Wang F, Kim YM, Kim SJ, Yoon JY (2009) Cu2+-selective ratiometric and “off-on” sensor based on the rhodamine derivative bearing pyrene group. Org Lett 11:4442–4445

    Article  PubMed  CAS  Google Scholar 

  23. Liu ZC, Wang BD, Yang ZY, Li TR, Li Y (2009) Synthesis, crystal structure, DNA interaction and antioxidant activities of two novel water-soluble Cu(2+) complexes derivated from 2-oxo-quinoline-3-carbaldehyde Schiff-bases. Eur J Med Chem 44:4477–4484

    Article  PubMed  CAS  Google Scholar 

  24. Yang Y-K, Yook K-J, Tae J (2005) A rhodamine-based fluorescent and colorimetric chemodosimeter for the rapid detection of Hg2+ ions in aqueous media. J Am Chem Soc 127:16760–16761

    Article  PubMed  CAS  Google Scholar 

  25. Nohara A, Umetani T, Sanno Y (1973) 1A facile synthesis of chromone-3- carboxaldehyde, chromone-3-carboxylic acid and 3-hydroxymethylchromone. Tetrahedron Lett 14:995–1998

    Article  Google Scholar 

  26. Li Y, Yang ZY, Li TR, Liu ZC, Wang BD (2011) Synthesis, characterization, DNA binding properties and antioxidant activity of Ln(III) complexes with Schiff base ligand derived from 3-carbaldehyde chromone and aminophenazone. J Fluoresc 21:1091–1102

    Article  PubMed  CAS  Google Scholar 

  27. Benesi HA, Hildebrand JH (1949) A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc 71:2703–2707

    Article  CAS  Google Scholar 

  28. Wang BD, Hai J, Liu ZC, Wang Q, Yang ZY, Sun SH (2010) Selective detection of iron(III) by rhodamine-modified Fe3O4 nanoparticles. Angew Chem Int Ed 49:4576–4579

    Article  CAS  Google Scholar 

Download references

Acknowledgments

This work is supported by the Research Start Funds Sponsored Program of Zhoukou Normal University (zksybscx201201) and the National Natural Science Foundation of China (81171337, 21271093).

Author information

Authors and Affiliations

  1. College of Chemistry, Zhoukou Normal University, Zhoukou, 466001, People’s Republic of China

    Zeng-chen Liu, Yan-xia Li & Yong-jie Ding

  2. The Key Laboratory of Rare Earth Functional Materials and Applications, Zhoukou, 466001, People’s Republic of China

    Zeng-chen Liu, Yan-xia Li & Yong-jie Ding

  3. Faculty of Material Science and Chemistry Engineering, China University of Geosciences, Wuhan, 430074, People’s Republic of China

    Yong Li

  4. College of Chemistry and Chemical Engineering and State Key Laboratory of Applied Organic Chemistry, Lanzhou University, Lanzhou, 730000, People’s Republic of China

    Zheng-yin Yang, Bao-dui Wang & Tian-rong Li

Authors
  1. Zeng-chen Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Zheng-yin Yang
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Yan-xia Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Bao-dui Wang
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Yong Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Tian-rong Li
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. Yong-jie Ding
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Zeng-chen Liu.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Liu, Zc., Yang, Zy., Li, Yx. et al. A Highly Selective Turn-On Fluorescent Chemosensor for Zinc Ion in Aqueous Media. J Fluoresc 23, 1239–1245 (2013). https://doi.org/10.1007/s10895-013-1255-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-013-1255-1

Keywords

Search

Navigation