Skip to main content
SpringerLink
Log in

A Novel Hg2+ Selective Ratiometric Fluorescent Chemodosimeter Based on an Intramolecular FRET Mechanism

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

Abstract

A irreversible Hg2+ selective ratiometric fluorescence probe FR, a fluorescein fluorophore linked to a rhodamine B hydrazide by a thiourea spacer, was designed and synthesized. The developed probe FR exhibited great ratiometric fluorescence enhancement and remarkable yellow-magenta color change toward Hg2+ with excellent selectivity in aqueous acetone solution, and the ratiometric fluorescence response to Hg2+ was not interfered by other metal cations including Fe3+, Co2+, Ni2+, Cr3+, Zn2+, Pb2+, Cd2+, Ca2+, Mg2+, Ba2+ and Mn2+. The linear range and the detection limit of this supposed ratiometric fluorescence method for Hg2+ were 0.0–10.0 × 10−6 and 5 × 10−8 M, respectively.

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

Fig. 1
Fig. 2
Scheme 1
Fig. 3
Scheme 2
Fig. 4

References

  1. Desvergne JP, Czarnik AW (1997) Chemosensors of Ion and Molecule Recognition. Kluwer, Dordrecht

    Google Scholar 

  2. Czarnik AW (ed) (1992) In: Fluorescent Chemosensors for Ion and Molecule Recognition. American Chemical Society, Washington, D.C.

  3. Hashem EY (2002) Spectrophotometric studies on the simultaneous determination of cadmium and mercury with 4-(2-pyridylazo)-resoreinol. Spectrochim Acta Part A 58:1401–1410

    Article  Google Scholar 

  4. Chatterjee S, Pillai A, Gupta VK (2002) Spectrophotometric determination of mercury in environmental sample and fungicides based on its complex with o-carboxy phenyl diazoamino p-azobenzene. Talanta 57:461–465

    Article  PubMed  CAS  Google Scholar 

  5. Ines O, Otto SW (1997) Optical sensors for dtermination of heavy metal ions. Microchimica Acta 126(3/4):177–192

    Google Scholar 

  6. Rurack K, Resch-Genger U, Bricks JL, Spieles M (2000) Cation-triggered ‘switching on’ of the red/near infra-red (NIR) fluorescence of rigid fluorophore-spacer-receptor ionophores. Chem Commun 2:2103–2104

    Article  Google Scholar 

  7. Talanova GG, Elkarim NSA, Talanov VS (1999) A calixarene-based Fluorogenic reagent for selective mercury(II) recognition. Anal Chem 71:3106–3109

    Article  CAS  Google Scholar 

  8. Kim JS, Gil Choi M, Song KC, Tai No K, Ahn S, Chang SK (2007) Ratiometric determination of Hg2+ ions based on simple molecular motifs of pyrene and dioxaoctanediamide. Org Lett 9:1129–1132

    Article  PubMed  CAS  Google Scholar 

  9. Zhang XB, Guo CCh, Li ZZ, Shen GL, Yu RQ (2002) An optical fiber chemical sensor for mercury ions based on a porphyrin dimer. Anal Chem 74(4):821–825

    Article  PubMed  CAS  Google Scholar 

  10. Torsten M, Christian I, Gregor L, Ingo K, Otto SW (2003) Cross-reactive metal ion sensor array in a micro titer plate format. Anal Chem 75(17):4389–4396

    Article  CAS  Google Scholar 

  11. Chan WH, Yang RH, Wang KM (2001) Development of a mercury ion-selective optical sensor based on fluorescence quenching of 5,10,15,20-tetraphenylporphyrin. Anal Chim Acta 444(2):261–269

    Article  CAS  Google Scholar 

  12. Wu FY, Zhao YQ, Ji ZJ, Wu YM (2007) A Highly Sensitive and Selective Fluorescent Chemodosimeter for Hg2+ in Neutral Aqueous Solution. J Fluoresc 17:460–465

    Article  PubMed  CAS  Google Scholar 

  13. Yang XF, Li Y, Bai Q (2007) A highly selective and sensitive fluorescein-based chemodosimeter for Hg2+ ions in aqueous media. Anal Chim Acta 584:95–100

    Article  PubMed  CAS  Google Scholar 

  14. Andrew AV, Ramaier N (1998) Optical fibre reflectance sensors for the detection of heavy metal ions based on immobilised Br-PADAP. Sens Actuators B Chem B51(1–3):368–376

    Google Scholar 

  15. Ivana M, Otto SW (1997) Fluorescence-based sensor membrane for mercury (II) detection. Sens Actuators B Chem B39(1–3):246–251

    Google Scholar 

  16. 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 

  17. 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 

  18. Guo X, Qian X, Jia L (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. 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 

  20. Kubo Y, Yamamoto M, Ikeda M, Takeuchi M, Shinkai S, Yamaguchi S, Tamao K (2003) A colorimetric and ratiometric fluorescent chemosensor with three Emission changes: fluoride ion sensing by a triarylborane–porphyrin conjugate. Angew Chem Int Ed 42:2036–2040

    Article  CAS  Google Scholar 

  21. Raker J, Glass TE (2002) Selectivity via cooperative interactions: detection of dicarboxylates in water by a pinwheel chemosensor. J Org Chem 67:6113–6116

    Article  PubMed  CAS  Google Scholar 

  22. Fu H, Loo BH, Xiao D, Xie R, Ji X, Yao J, Zhang B, Zhang L (2002) Multiple emissions from 1,3-diphenyl-5-pyrenyl-2-pyrazoline nanoparticles: evolution from molecular to nanoscale to bulk materials. Angew Chem Int Ed 41:962–965

    Article  CAS  Google Scholar 

  23. Mohr GJ, Klimant I, Spichiger UE, Wolfbeis OS (2001) Fluoro reactands and dual luminophore referencing: a technique to optically measure amines. Anal Chem 73:1053–1056

    Article  PubMed  CAS  Google Scholar 

  24. Mello JV, Finney NS (2001) Dual-signaling fluorescent chemosensors based on conformational restriction and induced charge transfer. Angew Chem Int Ed 40:1536–1538

    Article  CAS  Google Scholar 

  25. Takakusa H, Kikuchi K, Urano Y, Sakamoto S, Yamaguchi K, Nagano T (2002) Design and synthesis of an enzyme-cleavable sensor molecule for phosphodiesterase activity based on fluorescence resonance energy transfer. J Am Chem Soc 124:1653–1657

    Article  PubMed  CAS  Google Scholar 

  26. Coskun A, Deniz Yilmaz MU, Akkaya E (2007) Bis(2-pyridyl)-substituted boratriazaindacene as an NIR-emitting chemosensor for Hg(II). Org Lett 9:607–609

    Article  PubMed  CAS  Google Scholar 

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

    Article  CAS  Google Scholar 

  28. 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 

  29. Lakowicz JR (1999) Principles of Fluorescence Spectroscopy, 2nd edn. Plenum, New York

    Google Scholar 

  30. Nguyen T, Francis MB (2003) A practical synthetic route to functionalized rhodamine dyes. Org Lett 5:3245–3248

    Article  PubMed  CAS  Google Scholar 

  31. Dujols V, Ford F, Czarnik AW (1997) A long-wavelength fluorescent chemodosimeter selective for Cu(II) ion in water. J Am Chem Soc 119:7386–7387

    Article  CAS  Google Scholar 

  32. Wang X, Li Z, Wei B, Yang J (2002) Synthesis of 2-(4-methoxylphenyloxy-acetylamido)-5-aryloxymethyl-1,3,4-oxadiazoles under microwave irradiation. Synth Commun 32:1097–1103

    Article  CAS  Google Scholar 

  33. Zou X, Jin G (2001) Synthesis of pyridazininone-substituted 1,3,4-thiadiazoles-1,3,4-oxadiazoles and 1,2,4-triazoles. J Heterocycl Chem 38:993–996

    Article  CAS  Google Scholar 

Download references

Acknowledgment

This work was supported by the Science Research Foundation of Xiamen University (No.E43011) and the National Natural Science Foundation of China (No.20675067).

Author information

Authors and Affiliations

  1. Key Laboratory of Analytical Sciences, Ministry of Education, Department of Chemistry, College of Chemistry and Chemical Engineering, Xiamen University, Xiamen, 361005, China

    Gui-Qin Shang, Xia Gao, Mei-Xiu Chen, Hong Zheng & Jin-Gou Xu

Authors
  1. Gui-Qin Shang
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Xia Gao
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mei-Xiu Chen
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Hong Zheng
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Jin-Gou Xu
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Hong Zheng.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Shang, GQ., Gao, X., Chen, MX. et al. A Novel Hg2+ Selective Ratiometric Fluorescent Chemodosimeter Based on an Intramolecular FRET Mechanism. J Fluoresc 18, 1187–1192 (2008). https://doi.org/10.1007/s10895-008-0365-7

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-008-0365-7

Keywords

Search

Navigation