Skip to main content
Log in

A Highly Sensitive and Selective Fluorescent Chemodosimeter for Hg2+ in Neutral Aqueous Solution

  • Short Communication
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

A fluorescent assay of Hg2+ in neutral aqueous solution was developed using N-[p-(dimethylamino)benzamido]-N′-phenylthiourea (1). 1’s fluorogenic chemodosimetric behaviors towards various metal ions were studied and a high sensitivity as well as selectivity was achieved for Hg2+. It was because of a strongly fluorescent 1,3,4-oxadiazoles which was produced by the Hg2+ promoted desulfurization reaction. The spectra of ESI mass and IR provided evidences for this reaction. According to fluorescence titration, a good linear relationship ranging from 1.0 × 10−7 to 2.0 × 10−5 mol l−1 was obtained with the limit of detection as 3.1 × 10−8 mol l−1.

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

Access this article

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

Instant access to the full article PDF.

Fig. 1
Scheme 1
Fig. 2
Fig. 3
Fig. 4

References

  1. Clarkson TW, Magos L, Myers GJ (2003) The toxicology of mercury—Current exposures and clinical manifestations. Engl J Med 349:1731–1737

    Article  CAS  Google Scholar 

  2. Moreton JA, Delves HT (1998) Simple direct method for the determination of total mercury levels in blood and urine and nitric acid digests of fish by inductively coupled plasma mass spectrometry. J Anal At Spectrom 18:659–665

    Article  Google Scholar 

  3. de Silva AP, Gunaratne HQN, Gunnlaugsson T, Huxley AJM, CP McCoy, Rademacher JT, Rice TE (1997) Signaling recognition events with fluorescent sensors and switches Chem Rev 97:1515–1566

    Article  PubMed  Google Scholar 

  4. Valeur B, Leray I (2000) Design principles of fluorescent molecular sensors for cation recognition. Coord Chem Rev 205:3–40

    Article  CAS  Google Scholar 

  5. Sasaki DY, Padilla BE (1998) Dithioamide metal ion receptors on fluorescent lipid bilayers for the selective optical detection of mercuric ion. Chem Commun 18:1581–1582

    Article  Google Scholar 

  6. Talanova GG, Elkarim NSA, Talanov VS, Bartsch RA (1999) A Calixarene-based fluorogenic reagent for selective mercury(II) recognition. Anal Chem 71:3106–3109

    Article  CAS  Google Scholar 

  7. Feng K, Hsu FL, Bota K, Bu XR (2005) A potential fluorescent Hg(II) chemosensor. Microchem J 81:23–27

    Article  CAS  Google Scholar 

  8. Moon, SY, Youn NJ, Park SM, Chang SK (2005) Diametrically disubstituted cyclam derivative having Hg2+-selective fluoroionophoric behaviors. J Org Chem 70:2394–2397

    Article  PubMed  CAS  Google Scholar 

  9. Gao S, Tan G, Yuan H, Xiao D, Choi MMF (2006) A simple fluorometric method using chlorophyll a for determination of Hg2+ ion. Microchim Acta 153:159–162

    Article  CAS  Google Scholar 

  10. Yu Y, Lin LR, Yang KB, Zhong X, Huang RB, Zheng LS (2006) p-Dimethylamino-benzaldehyde thiosemicarbazone: a simple novel selective and sensitive fluorescent sensor for mercury(II) in aqueous solution. Talanta 69:103–106

    Article  CAS  Google Scholar 

  11. Gosh P, Bharadwaj PK, Roy J, Ghosh S (1997) Transition metal (II)/(III), Eu(III), and Tb(III) ions induced molecular photonic OR gates using trianthryl cryptands of varying cavity dimension. J Am Chem Soc 119:11903–11909

    Article  Google Scholar 

  12. Zheng H, Qian ZH, Xu L, Yuan FF, Lan LD, Xu JG (2006) Switching the recognition preference of rhodamine B spirolactam by replacing one atom: design of rhodamine B thiohydrazide for recognition of Hg(II) in aqueous solution. Org Lett 8:859–861

    Article  PubMed  CAS  Google Scholar 

  13. Kim SH, Kim JS, Park SM, Chang SK (2006) Hg2+-selective off–on and Cu2+-selective on–off type fluoroionophore based upon cyclam. Org Lett 8:371–374

    Article  PubMed  CAS  Google Scholar 

  14. Mello JV, Finney NS (2005) Reversing the discovery paradigm: a new approach to the combinatorial discovery of fluorescent chemosensors. J Am Chem Soc 127:10124–10125

    Article  PubMed  CAS  Google Scholar 

  15. Zhu XJ, Fu ST, Wong WK, Guo JP, Wong WY (2006) A near-infrared-fluorescent chemodosimeter for mercuric ion based on an expanded porphyrin. Angew Chem Int Ed 45:3150–3154

    Article  CAS  Google Scholar 

  16. Chen QY, Chen CF (2005) A new Hg2+-selective fluorescent sensor based on a dansyl amide-armed calix[4]-aza-crown. Tetrahendron Lett 46:165–168

    Article  Google Scholar 

  17. Nolan EM, Racine ME, Lippard SJ (2006) Selective Hg(II) detection in aqueous solution with thiol derivatized fluoresceins. Inorg Chem 45:2742–2749

    Article  PubMed  CAS  Google Scholar 

  18. Guo XF, Qian XH, Jia LH (2004) A highly selective and sensitive fluorescent chemosensor for Hg2+ in neutral buffer aqueous solution. J Am Chem Soc 126:2272–2273

    Article  PubMed  CAS  Google Scholar 

  19. Nolan EM, Lippard SJ (2003) A “turn-on” fluorescent sensor for the selective detection of mercuric ion in aqueous media. J Am Chem Soc 125:14270–14271

    Article  PubMed  CAS  Google Scholar 

  20. Nolan EM, lippard SJ (2005) MS4, a seminaphthofluorescein-based chemosensor for the ratiometric detection of Hg(II). J Mater Chem 15:2778–2783

    Article  CAS  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. Descalzo AB, Mártinez-Máñez R, Radeglia R, Rurack K, Soto J (2003) Coupling selectivity with sensitivity in an integrated chemosensor framework: design of a Hg2+-responsive probe, operating above 500 nm. J Am Chem Soc 125:3418–3419

    Article  PubMed  CAS  Google Scholar 

  23. Prodi L, Bargossi C, Montalti M, Zaccheroni N, Su N, Bradshaw JS, Izatt RM, Savage PB (2000) An effective fluorescent chemosensor for mercury ions. J Am Chem Soc 122:6769–6770

    Article  CAS  Google Scholar 

  24. Tang Y, He F, Yu M, Feng F, An L, Sun H, Li Y, Zhu D (2006) A reversible and highly selective fluorescent sensor for mercury(II) using poly(thiophene)s that contain thymine moieties. Macromol Rapid Commun 27:389–392

    Article  CAS  Google Scholar 

  25. Cai ZX, Yang H, Zhang Y, Yan XP (2006) Preparation, characterization and evaluation of water-soluble l-cysteine-capped-CdS nanoparticles as fluorescence probe for detection of Hg(II) in aqueous solution. Anal Chim Acta 559:234–239

    Article  CAS  Google Scholar 

  26. Matsushita M, Meijler MM, Wirsching P, Lerner RA, Janda KD (2005) A blue fluorescent antibody-cofactor sensor for mercury. Org Lett 7:4943–4946

    Article  PubMed  CAS  Google Scholar 

  27. Ono A, Togashi H (2004) Highly selective oligonucleotide-based sensor for mercury(II) in aqueous solutions. Angew Chem Int Ed 43:4300–4302

    Article  CAS  Google Scholar 

  28. Song KC, Kim JS, Park SM, Chung KC, Ahn S, Chang SK (2006) Fluorogenic Hg2+-selective chemodosimeter derived from 8-Hydroxyquinoline. Org Lett 8:3413–3416

    Article  PubMed  CAS  Google Scholar 

  29. Yang YK, Yook KJ, 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 

  30. Ros-Lis JV, Marcos MD, Mártinez-Máñez R, Rurack K, Soto J (2005) A regenerative chemodosimeter based on metal-induced dye formation for the highly selective and sensitive optical determination of Hg2+ ions. Angew Chem Int Ed 44:4405–4407

    Article  CAS  Google Scholar 

  31. Zhang G, Zhang D, Yin S, Yang X, Shuai Z, Zhu D (2005) 1,3-Dithiole-2-thione derivatives featuring an anthracene unit: new selective chemodosimeters for Hg(II) ion. Chem Commun 25:2161–2163

    Article  Google Scholar 

  32. Liu B, Tian H (2005) A selective fluorescent ratiometric chemodosimeter for mercury ion. Chem Commun 25:3156–3158

    Article  Google Scholar 

  33. Hennrich G, Sonnenschein H, Genger UR (1999) Redox switchable fluorescent probe selective for either Hg(II) or Cd(II) and Zn(II). J Am Chem Soc 121:5073–5074

    Article  CAS  Google Scholar 

  34. Ji ZJ, Wu YM, Wu FY (2006) A ratiometric fluorescence sensor for zinc in neutral solution based on thiourea receptor. Chem Lett 15:950–951

    Article  Google Scholar 

Download references

Acknowledgements

The authors gratefully acknowledge the financial support of this study by the State Key Laboratory of Chemo/Biosensing and Chemometrics of Hunan University (no. 2005018), Jiangxi Province Natural Science Foundation (JXNSF no. 0420041), Jiangxi Province Education Ministry Foundation (no. 2005-38). We would also like to thank Prof. YunBao Jiang from Xiamen University for his kind support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Fang-Ying Wu.

Electronic Supplementary Material

Below is the link to the electronic supplementary material.

ESM 1

(DOC 90.6 KB)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Wu, FY., Zhao, YQ., Ji, ZJ. et al. A Highly Sensitive and Selective Fluorescent Chemodosimeter for Hg2+ in Neutral Aqueous Solution. J Fluoresc 17, 460–465 (2007). https://doi.org/10.1007/s10895-007-0212-2

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-007-0212-2

Keywords

Navigation