Skip to main content
Log in

A Highly Selective Fluorescent Chemosensor for the Detection of Picrate Anion Based on 1,8-Naphthalimide Derivatives

  • Published:
Journal of Applied Spectroscopy Aims and scope

The synthesis and spectral characteristics of a new fluorescent N-allyl-4-iminodi(N-benzylacetamide)-1,8-naphthalimide (Zabe) sensor were reported. The ability of this new compound to detect anions was evaluated by spectrophotometrically monitoring the changes in the fluoresence intensity performed on its N,N-dimethylformamide (DMF) solution. Compared to other anions examined, only picrate (Pic) generated a prominent fluorescence quenching at 516 nm. No significant fluorescence change was observed in the presence of other anions. The emission quenching was due to the enhanced photoinduced electron transfer (PET) from the receptor to the excited state of the fluorophore upon the recognition of picrate. The chemosensor can be applied to the quantification of picrate with a linear range from 4.97 × 10−6 to 6.82 × 10−5 M and a detection limit of 6.6 × 10−7 M. Most importantly, this sensor can be utilized for the spectroscopic detection of picrate in the presence of other competing anions. Moreover, the response time of the chemo sensor is less than 1 min.

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.

Similar content being viewed by others

References

  1. P. D. Beer and P. A. Gale, Angew. Chem. Int. Ed., 40, 486–516 (2001).

    Article  Google Scholar 

  2. L. Fabbrizzi, M. Licchelli, and G. Rabaioli, A. Taglietti, Coordin. Chem. Rev., 205, 85–120 (2000).

    Article  Google Scholar 

  3. J. Zhao, T. M. Fyles, and T. D. James, Angew. Chem. Int. Ed., 43, 3461–3464 (2004).

    Article  Google Scholar 

  4. P. A. Gale, Accoun. Chem. Res., 39, 465–475 (2006).

    Article  Google Scholar 

  5. V. Pimienta, R. Etchenique, and T. Buhse, J. Phys. Chem. A, 105, 10037–10044 (2001).

    Article  Google Scholar 

  6. J. Y. Shen, J. F. Zhang, Y. Zuo, L. J. Wang, X. Y. Sun, J. S. Li, W. Q. Han, and R. He, J. Hazard. Mater., 163, 1199–1206 (2009).

    Article  Google Scholar 

  7. R. Mantha, K. E. Taylor, N. Biswas, and J. K. Bewtra, Environ. Sci. Technol., 35, 3231–3236 (2001).

    Article  ADS  Google Scholar 

  8. F. D. Marvin-Sikkema and J. A. M. de Bont, Appl. Microbiol. Biotechnol., 42, 499–507 (1994).

    Article  Google Scholar 

  9. C. Beyer, U. Böhme, C. Pietzsch, and G. Roewer, J. Organomet. Chem., 654, 187–201 (2002).

    Article  Google Scholar 

  10. H. Muthurajan, R. Sivabalan, M. B. Talawar, and S. N. Asthana, J. Hazard. Mater., 112, 17–33 (2004).

    Article  Google Scholar 

  11. T. H. Ma, M. Dong, Y. M. Dong, Y. W. Wang, and Y. Peng, Chem. Eur. J., 16, 10313–10318 (2010).

    Article  Google Scholar 

  12. M. Dong, Y. W. Wang, and Y. Peng, Org. Lett., 12, 5310–5313 (2010).

    Article  Google Scholar 

  13. Y. Salinas, R. Martínez-Máñez, M. D. Marcos, F. Sancenón, A. M. Costero, M. Parra, and S. Gil, Chem. Soc. Rev., 41, 1261–1296 (2012).

    Article  Google Scholar 

  14. Y. Q. Xu, B. H. Li, W. W. Li, J. Zhao, S. G. Sun, and Y. Pang, Chem. Commun., 49, 4764–4766 (2013).

    Article  Google Scholar 

  15. S. Singh, J. Hazard. Mater., 144, 15–28 (2007).

    Article  Google Scholar 

  16. M. E. Germain and M. J. Knapp, Chem. Soc. Rev., 38, 2543–2555 (2009).

    Article  Google Scholar 

  17. J. F. Callan, A. P. de Silva, and D. C Magri, Tetrahedron, 6 1, 8551–8588 (2005).

  18. W. Zhu, N. Minami, S. Kazaoui, and Y. Kim, J. Mater. Chem., 13, 2196–2201 (2003).

    Article  Google Scholar 

  19. Z. F. Tao and X. Qian, Dyes and Pigments, 43, 139–145 (1999).

    Article  Google Scholar 

  20. V. B. Bojinov, N. I. Georgiev, and N. V. Marinova, Sens. Actuators, B, Chem., 148, 6–16 (2010).

  21. L. Patrick and A. Whiting, Dyes and Pigments, 55, 123–132 (2002).

    Article  Google Scholar 

  22. V. B. Bojinov and I. P. Panova, Dyes and Pigments, 74, 551–560 (2007).

    Article  Google Scholar 

  23. J. Kollár, P. Hrdlovič, and Š. Chmela, J. Photochem. Photobiol. A: Chem., 195, 64–71 (2008).

    Article  Google Scholar 

  24. W. H. Zhu, C. Hu, K. C. Chen, and H. Tian, Synth. Met., 96, 151–154 (1998).

    Article  Google Scholar 

  25. V. Gruzinskii, A. Kukhto, and G. Shakkah, J. Appl. Spectrosc., 65, 463–465 (1998).

    Article  ADS  Google Scholar 

  26. W. H. Zhu, M. Hu, R. Yao, and H. Tian, J. Photochem. Photobiol., A, Chem., 154, 169–177 (2003).

    Article  Google Scholar 

  27. W. W. Stewart, J. Am. Chem. Soc., 103, 7615–7620 (1981).

    Article  Google Scholar 

  28. H. Tian, J. Gan, K. C. Chen, J. He, Q. L. Song, and X. Y. Hou, J. Mater. Chem., 12, 1262–1267 (2002).

    Article  Google Scholar 

  29. C. Y. Li, F. Xua, Y. F. Li, K. Zhou, and Y. Zhou, Anal. Chim. Acta, 717, 122–126 (2012).

    Article  Google Scholar 

  30. I. Grabchev, X. H. Qian, V. Bojinov, and Y. Xiao, W. Zhang, Polymer, 43, 5731–5736 (2002).

    Article  Google Scholar 

  31. V. B. Bojinov and T. N. Konstantinova, Sens. Actuators, B, Chem., 123, 869–876 (2007).

  32. N. I. Georgiev and V. B. Bojinov, J. Lumin., 132, 2235–2241 (2012).

    Article  Google Scholar 

  33. H. Yang, H. S. Song, Y. C. Zhu, and S. P. Yang, Tetrahedron Lett., 53, 2026–2029 (2012).

    Article  Google Scholar 

  34. P. G. Jones, J. Ossowski, and P. Kus, Z. Naturforsch. B, 57, 914–921 (2002).

    Google Scholar 

  35. T. N. Konstantinova, P. Meallier, and I. Grabchev, Dyes and Pigments, 22, 191–198 (1993).

    Article  Google Scholar 

  36. C. G. Niu, X. Yang, W. Q. Lin, G. L. Shen, and R. Q. Yu, Analyst, 127, 512–517 (2002).

    Article  ADS  Google Scholar 

  37. R. Parkesh, T. C. Lee, and T. Gunnlaugsson, Org. Biomol. Chem., 5, 310–317 (2007).

    Article  Google Scholar 

  38. C. C. Wang, S. Feng, L. Y. Wu, S. Y. Yan, C. Zhong, P. Guo, R. Huang, X. C. Weng, and X. Zhou, Sens. Actuators, B, Chem., 190, 792–799 (2014).

    Article  Google Scholar 

  39. E. H. Lu, X. J. Peng, F. L. Song, and J. L. Fan, Bioorg. Med. Chem. Lett., 15, 255–257 (2005).

    Article  Google Scholar 

  40. C. G. Niu, G. M. Zeng, L. X. Chen, G. L. Shen, and R. Q. Yu, Analyst, 129, 20–24 (2004).

    Article  ADS  Google Scholar 

  41. V. B. Bojinov, I. P. Panova, and J. M. Chovelon, Sens. Actuators, B, Chem., 135, 172–180 (2008).

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to H.-L. Wu.

Additional information

Published in Zhurnal Prikladnoi Spektroskopii, Vol. 84, No. 1, pp. 33–38, January–February, 2017.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Wu, HL., Aderinto, S.O., Xu, YL. et al. A Highly Selective Fluorescent Chemosensor for the Detection of Picrate Anion Based on 1,8-Naphthalimide Derivatives. J Appl Spectrosc 84, 25–30 (2017). https://doi.org/10.1007/s10812-017-0421-7

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10812-017-0421-7

Keywords

Navigation