Skip to main content
SpringerLink
Log in

Multispectroscopic and theoretical studies on rapid, selective and sensitive visual sensing of cyanide ion in aqueous solution by receptors possessing varying HBD property

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

Three new benzoquinone–imidazole ensembles possessing varying number (0, 1 and 2) of electron-withdrawing bromo substituents on the quinone ring have been designed, synthesized, characterized and employed as receptors in cyanide sensing. These receptors colorimetrically sense cyanide ion selectively and sensitively in aq. 4-(2-hydroxyethyl)-1-piperazineethanesulphonic acid (HEPES) buffer–acetonitrile (ACN) (8:2 v/v) medium with striking colour change that can easily be seen visually. Fluorescence spectral studies revealed that the receptors form strong complex at 1:1 stoichiometry with cyanide ion. The binding constants for the complexes were found to be in the order of 105–107 M−1 and increase with increasing number of bromo substituents on the quinone ring. The detection limit of cyanide by these receptors lay in the range of 10−8 M. The effects of the number of bromo substituents on the absorption maximum, reduction potential and H-bond donor (HBD) property of imidazole N–H are discussed. The results of spectral studies corroborate well with those of electrochemical and theoretical studies. An easy-to-use test strip was prepared to test cyanide in aqueous solution of sodium cyanide prepared using deep-well water.

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
Scheme 2
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. Q. Li, J.H. Zhang, Y. Cai, W.J. Qu, G.Y. Gao, Q. Lin, H. Yao, Y.M. Zhang, T.B. Wei, Tetrahedron 71, 857 (2015)

    Article  CAS  Google Scholar 

  2. V. Amendola, D.E. Gomez, L. Fabbrizzi, M. Licchelli, Acc. Chem. Res. 39, 343 (2006)

    Article  CAS  Google Scholar 

  3. C. Suksai, T. Tuntulani, Chem. Soc. Rev. 32, 192 (2003)

    Article  CAS  Google Scholar 

  4. T.Z. Sadyrbaeva, Sep. Purif. Technol. 86, 262 (2012)

    Article  CAS  Google Scholar 

  5. V.K. Sharma, C.R. Burnett, R.A. Yngard, D.E. Cabelli, Environ. Sci. Technol. 39, 3849 (2005)

    Article  CAS  Google Scholar 

  6. K. Naicker, E. Cukrowska, T.S. McCarthy, Environ. Pollut. 122, 29 (2003)

    Article  CAS  Google Scholar 

  7. Y.C. Yang, J.A. Barker, J.R. Ward, Chem. Rev. 92, 1729 (1992)

    Article  CAS  Google Scholar 

  8. G.Q. Liu, W.T. Yen, Miner. Eng. 8, 111 (1995)

    Article  CAS  Google Scholar 

  9. Q. Lin, Y. Cai, Q. Li, B.B. Shi, H. Yao, Y.M. Zhang, T.B. Wei, Spectrochim. Acta A 141, 113 (2015)

    Article  CAS  Google Scholar 

  10. K. Wang, Z. Liu, R. Guan, D. Cao, H. Chen, Y. Shan, Q. Wu, Y. Xu, Spectrochim. Acta A 144, 235 (2015)

    Article  CAS  Google Scholar 

  11. F. Huo, J. Kang, C. Yin, J. Chao, Y. Zhang, Sens. Actuators B 215, 93 (2015)

    Article  CAS  Google Scholar 

  12. R. Manivannan, A. Satheshkumar, K.P. Elango, New J. Chem. 37, 3125 (2013)

    Article  Google Scholar 

  13. R. Manivannan, S. Ciattini, L. Chelazzi, K.P. Elango, RSC Adv. 5, 87341 (2015)

    Article  CAS  Google Scholar 

  14. J.B. Li, J.H. Hu, J.J. Chen, J. Qi, Spectrochim. Acta A 133, 773 (2014)

    Article  CAS  Google Scholar 

  15. N. Kumari, S. Jha, S. Bhattacharya, J. Org. Chem. 76, 8215 (2011)

    Article  CAS  Google Scholar 

  16. L. Tang, M. Cai, Z. Huang, K. Zhong, S. Hou, Y. Bian, R. Nandhakumar, Sens. Actuators B 185, 188 (2013)

    Article  CAS  Google Scholar 

  17. M. Sun, H. Yu, H. Li, H. Xu, D. Huang, S. Wang, Inorg. Chem. 54, 3766 (2015)

    Article  CAS  Google Scholar 

  18. P. Hammershoj, T.K. Reenberg, M. Pittelow, C. B. Nielsen, O. Hammerich, J.B. Christensen, Eur. J. Org. Chem. 2006, 2796 (2006)

    Article  Google Scholar 

  19. L. Garuti, M. Roberti, N. Malagoli, P. Rossi, M. Castelli, Bioorg. Med. Chem. Lett. 10, 2193 (2000)

    Article  CAS  Google Scholar 

  20. P. Jayasudha, R. Manivannan, S. Ciattini, L. Chelazzi, K.P. Elango, Sens. Actuators B 242, 736 (2017)

    Article  CAS  Google Scholar 

  21. P. Jayasudha, R. Manivannan, K.P. Elango, RSC Adv. 6, 25473 (2016)

    Article  CAS  Google Scholar 

  22. P. Jayasudha, R. Manivannan, K.P. Elango, Sens. Actuators B 221, 1441 (2015)

    Article  CAS  Google Scholar 

  23. J. Ma, Y. Liu, L. Chen, Y. Xie, L.Y. Wang, M.X. Xie, Food Chem. 132, 663 (2012)

    Article  CAS  Google Scholar 

  24. Q. Lin, X. Liu, T.B. Wei, Y.M. Zhang, Chem. Asian J. 8, 3015 (2013)

    Article  CAS  Google Scholar 

  25. S. Park, K.H. Hong, J.I. Hong, H.J. Kim, Sens. Actuators B 174, 140 (2012)

    Article  CAS  Google Scholar 

  26. Y. Yan, H. Yu, K. Zhang, M. Sun, Y. Zhang, X. Wang, S. Wang, Nano Res. 9, 2088 (2016)

    Article  CAS  Google Scholar 

  27. Y. Zhang, L. Guan, H. Yu, Y. Yan, L. Du, Y. Liu, M. Sun, D. Huang, S. Wang, Anal. Chem. 88, 4426 (2016)

    Article  CAS  Google Scholar 

  28. H. Yu, L. Du, L. Guan, K. Zhang, Y. Li, H. Zhu, M. Sun, S. Wang, Sens. Actuators B 247, 823 (2017)

    Article  CAS  Google Scholar 

  29. V.A. Nikitina, R.R. Nazmutdinov, G.A. Tsirlina, J. Phys. Chem. B 115, 668 (2011)

    Article  CAS  Google Scholar 

  30. M.J. Frisch, G.W. Trucks, H.B. Schlegel, G.E. Scuseria, M.A. Robb, J.R.Cheeseman, J.A. Montgomery Jr., T. Vreven, K.N. Kudin, J.C. Burant, J.M. Millam, S.S. Iyengar, J. Tomasi, V. Barone, B. Mennucci, M. Cossi, G. Scalmani, N. Rega, G.A. Petersson, H. Nakatsuji, M. Hada, M. Ehara, K. Toyota, R. Fukuda, J. Hasegawa, M. Ishida, T. Nakajima, Y. Honda, O. Kitao, H. Nakai, M. Klene, X. Li, J.E. Knox, H.P. Hratchian, J.B. Cross, V. Bakken, C. Adamo, J. Jaramillo, R. Gomperts, R.E. Stratmann, O. Yazyev, A.J. Austin, R. Cammi, C. Pomelli, J.W. Ochterski, P.Y. Ayala, K. Morokuma, G.A. Voth, P. Salvador, J.J. Dannenberg, V.G. Zakrzewski, S. Dapprich, A.D. Daniels, M.C. Strain, O. Farkas, D.K. Malick, A.D. Rabuck, K. Raghavachari, J.B. Foresman, J.V. Ortiz, Q. Cui, A.G. Baboul, S. Clifford, J. Cioslowski, B.B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R.L. Martin, D.J. Fox, T. Keith, M.A. Al-Laham, C. Y. Peng, A. Nanayakkara, M. Challacombe, P.M.W. Gill, B. Johnson, W. Chen, M.W. Wong, C. Gonzalez, J.A. Pople, Gaussian 03, Revision D.01, Gaussian, Inc., Wallingford CT (2004)

  31. N.M. Ruvalcaba, G. Cuevas, I. Gonzalez, M. Amartinez, J. Org. Chem. 67, 3673 (2002)

    Article  Google Scholar 

Download references

Author information

Authors and Affiliations

  1. Department of Chemistry, Gandhigram Rural Institute (Deemed to be University), Gandhigram, 624302, India

    P. Raja Lakshmi, R. Manivannan, P. Jayasudha & Kuppanagounder P. Elango

Authors
  1. P. Raja Lakshmi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. R. Manivannan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. P. Jayasudha
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Kuppanagounder P. Elango
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Kuppanagounder P. Elango.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (PDF 2734 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Raja Lakshmi, P., Manivannan, R., Jayasudha, P. et al. Multispectroscopic and theoretical studies on rapid, selective and sensitive visual sensing of cyanide ion in aqueous solution by receptors possessing varying HBD property. Res Chem Intermed 44, 2807–2821 (2018). https://doi.org/10.1007/s11164-018-3262-y

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-018-3262-y

Keywords

Search

Navigation