Skip to main content
Log in

Indole-based Fluorescent Sensors for Selective Detection of Hg2+

  • SHORT COMMUNICATION
  • Published:
Journal of Fluorescence Aims and scope Submit manuscript

Abstract

A series of indole-based fluorescent chemosensors 14 were prepared and investigated characteristick features with transition metal ions. Sensors 1 and 2 were selective for Hg2+ ion among a series of metal ions in H2O–DMSO with association constants of 4.60×104 and 5.90×104 M−1 and detection limits of 140 and 101.6 μM, respectively.

Indole-Based Fluorescent Sensors for Selective Detection of Hg2+.

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
Fig. 2
Fig. 3
Fig. 4
Fig. 5

References

  1. Formica M, Fusi C, GIorgi L, Micheloni M (2012) New fluorescent chemosensors for metal ions in solution. Coord Chem Rev 256:170–192

    Google Scholar 

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

    Google Scholar 

  3. Rocha A, Marques MMB, Lodeiro C (2009) Synthesis and characterization of novel indole-containing half-crowns as new emissive metal probes. Tetrahedron Lett 50:4930–4933

    Google Scholar 

  4. Adams PD, Chen Y, Ma K, Zagorski MG, Sonnichsen FD, McLaughlin ML, Barkley MD (2002) Intramolecular quenching of tryptophan fluorescence by the peptide bond in cyclic hexapeptides. J Am Chem Soc 124:9278–9286

    Google Scholar 

  5. Liu B, Thalji RK, Adams PD, Fronczek FR, McLaughlin ML, Barkley MDJ (2002) Fluorescence of cis-1-amino-2-(3-indolyl)cyclohexane-1-carboxylic acid: a single tryptophan χ1 rotamer model. J Am Chem Soc 124:13329–13338

    Google Scholar 

  6. Shizuka J, Serizawa M, Kobayashi J, Kameta K, Sugiyama H, Matsuura T, Saito IJ (1988) Excited-state behavior of tryptamine and related indoles. Remarkably efficient intramolecular proton-induced quenching. J Am Chem Soc 110:1726–1732

    Google Scholar 

  7. Sessler JL, Cho DG, Lynch V (2006) Diindolylquinoxalines: effective indole-based receptors for phosphate anion. J Am Chem Soc 128:16518–16519

    Google Scholar 

  8. He X, Hu S, Liu K, Guo Y, Xu J, Shao S (2006) Oxidized bis(indolyl)methane: a simple and efficient chromogenic-sensing molecule based on the proton transfer signaling mode. Org Lett 8:333–336

    Google Scholar 

  9. Li L, Dang YQ, Li HW, Wang B, Wu Y (2010) Fluorescent chemosensor based on Schiff base for selective detection of zinc(II) in aqueous solution. Tetrahedron Lett 51:618–621

    Google Scholar 

  10. Hsieh YC, Chir JL, Yang ST, Chen SJ, Hu CH, Wu AT (2011) A sugar-aza-crown ether-based fluorescent sensor for Cu2+ and Hg2+ ions. Carbohydr Res 346:978–981

    Google Scholar 

  11. Wu HH, Sun YL, Wan CF, Yang ST, Chen SJ, Hu CH, Wu AT (2012) Highly selective and sensitive fluorescent chemosensor for Hg2+ in aqueous solution. Tetrahedron Lett 53:1169–1172

    Google Scholar 

  12. Grandjean P, Weihe P, White RF, Debes F (1998) Cognitive performance of children prenatally exposed to ‘‘Safe’’ levels of methylmercury. Environ Res 77:165–172

    Google Scholar 

  13. Yuan M, Li Y, Li J, Li C, Liu X, Lv J, Xu J, Liu H, Wang S, Zhu D (2007) A colorimetric and fluorometric dual-modal assay for mercury ion by a molecule. Org Lett 9:2313–2316

    Google Scholar 

  14. Zhu M, Yuan M, Liu X, Xu J, Lv J, Huang C, Liu H, Li Y, Wang S, Zhu D (2008) Visible near-infrared chemosensor for mercury ion. Org Lett 10:1481–1484

    Google Scholar 

  15. Kao T-L, Wang C-C, Pan Y-T, Shiao Y-J, Yen J-Y, Shu C-M, Lee G-H, Peng S-M, Chung W-S (2005) Upper rim allyl- and arylazo-coupled calix[4]arenes as highly sensitive chromogenic sensors for Hg2+ ion. J Org Chem 70:2912–2920

    Google Scholar 

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

    Google Scholar 

  17. Moon SY, Cha NR, Kim YH, Chang SKJ (2004) New Hg2+-selective chromo-and fluoroionophore based upon 8-hydroxyquinoline. Org Chem 69:181–183

    Google Scholar 

  18. Cha NR, Kim MY, Kim YH, Choe J-I, Chang S-K (2002) New Hg2+-selective fluoroionophores derived from p-tert-butylcalix[4]arene–azacrown ethers. J Chem Soc Perkin Trans 2:1193–1196

    Google Scholar 

  19. Kumar A, Pandey PS (2009) Steroidal 1,2,3-triazole-based sensors for Hg2+ ion and their logic gate behavior. Tetrahedron Lett 50:5842–5845

    Google Scholar 

Download references

Acknowledgement

We thank the National Science Council of Taiwan for financial support.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to An-Tai Wu.

Electronic supplementary material

Below is the link to the electronic supplementary material.

ESM 1

The experimental procedures and the 1H NMR, 13C NMR and ESI-MS spectra are available. Supplementary data associated with this article can be found. (DOC 1286 kb)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Sun, YL., Wu, AT. Indole-based Fluorescent Sensors for Selective Detection of Hg2+ . J Fluoresc 23, 629–634 (2013). https://doi.org/10.1007/s10895-013-1190-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10895-013-1190-1

Keywords

Navigation