Advertisement

4-Functionalized terpyridine derivative as dual responsive chemosensor for biologically important inorganic cations and fluoride anion

  • Sethu Amuthakala
  • Dominic Savio Arumai Selvan
  • Aziz Kalilur RahimanEmail author
Original Paper
  • 21 Downloads

Abstract

A dual responsive sensor molecule, 2-(4-(2,2′:6′,2″-terpyridin)-4′-yl-phenyl)-N-methyl-3-thiosemicarbazone, has been synthesized and characterized using standard analytical and spectroscopic techniques. The dual binding properties of the sensor molecule were investigated using biologically important inorganic cations (Mn2+, Fe2+, Ni2+, Cu2+, Zn2+, Pb2+ and Hg2+) and anions (F¯, Cl¯, Br¯, I¯, HSO4¯ and H2PO4¯). The sensor molecule is equipped with analyte coordinating donor sites displaying charge transfer controlled spectroscopic properties and shows analyte–receptor interactions. Sensing mechanism involving host–guest interactions was confirmed by spectral and cyclic voltammetry techniques. The receptor shows colorimetric signalling in solution for cations such as Mn2+, Ni2+ and Cu2+ as evidenced by instant colour changes even at 2 μL aliquots of manganese and copper cations, and 4 μL aliquot for nickel cation, among the studied cations. Fluoride anion was detected by naked eye even at 2 μL of aliquot, signalled by the development of yellowish brown colour, through hydrogen bonding, deprotonation of N–H fragment and formation of HF2¯. Thus, the receptor shows dual sensing ability towards selected cations and F¯ anion. Further, paper strip experiments on receptor were also employed for the detection of cations and fluoride anion in solution.

Keywords

Terpyridine derivative Bifunctional chemosensor Colorimetric sensor Absorption titration Sensing mechanism 

Notes

Acknowledgements

The authors thank Sophisticated Instrumentation Facility (SIF), Chemistry Division, School of Advanced Sciences, VIT, Vellore—632 014, for providing NMR spectral facility.

Supplementary material

13738_2019_1851_MOESM1_ESM.doc (2.4 mb)
Supplementary material 1 (DOC 2479 kb)

References

  1. 1.
    M.M.M. Raposo, B.G. Acosta, T. Abalos, P. Calero, R. Manez, J.V.R. Lis, J. Soto, J. Org. Chem. 75, 2922 (2010)PubMedCrossRefGoogle Scholar
  2. 2.
    S.M. Basheer, A.C. Wills, R.J. Pace, A. Sreekanth, Polyhedron 109, 7 (2016)CrossRefGoogle Scholar
  3. 3.
    S. Das, S. Karmakar, S. Mardanya, S. Baitalik, Dalton Trans. 43, 3767 (2014)PubMedCrossRefGoogle Scholar
  4. 4.
    S. Karmakar, D. Maity, S. Mardanya, S. Baitalik, Dalton Trans. 44, 18607 (2015)PubMedCrossRefGoogle Scholar
  5. 5.
    M. Cametti, K. Rissanen, Chem. Commun. 20, 2809 (2009)CrossRefGoogle Scholar
  6. 6.
    A. Mohammadi, J. Jabbari, Can. J. Chem. 94, 631 (2016)CrossRefGoogle Scholar
  7. 7.
    A. Mohammadi, B. Khalili, A.S. Haghayegh, Spectrochim. Acta A 222, 117193 (2019)CrossRefGoogle Scholar
  8. 8.
    G.U. Priimov, P. Moore, L. Helm, A.E. Merbach, Inorg. React. Mech. 3, 1 (2001)Google Scholar
  9. 9.
    A.C. Benniston, A. Harriman, P. Li, C.A. Sams, J. Am. Chem. Soc. 127, 2553 (2005)PubMedCrossRefGoogle Scholar
  10. 10.
    S. Jing, C. Zheng, S. Pu, C. Fan, G. Liu, Dyes Pigm. 107, 38 (2014)CrossRefGoogle Scholar
  11. 11.
    W.B. Mefteh, H. Touzi, F. Bessueille, Y. Chevalier, R. Kalfat, N. Jaffrezic-Renault, Electroanal. 27, 84 (2015)CrossRefGoogle Scholar
  12. 12.
    T. Mutai, J.D. Cheon, S. Arita, K. Araki, J. Chem. Soc. 2, 1045 (2001)Google Scholar
  13. 13.
    P.A. Gale, Coord. Chem. Rev. 240, 191 (2003)CrossRefGoogle Scholar
  14. 14.
    J. Mahoney, J.P. Davis, A.M. Beatty, B.D. Smith, J. Org. Chem. 68, 9819 (2003)PubMedCrossRefPubMedCentralGoogle Scholar
  15. 15.
    P. Molina, A. Tarraga, A. Caballero, Eur. J. Inorg. Chem. 22, 340 (2008)Google Scholar
  16. 16.
    M.A. Abdalrahman, F. Abebe, J. Briggs, W.S. Kassel, S.C. Burdette, W.R. Seitz, R.P. Planalp, J. Coord. Chem. 70, 1123 (2017)CrossRefGoogle Scholar
  17. 17.
    J. You, H. Jeong, H. Seo, S. Jeon, Sens. Actuators B Chem. 146, 160 (2010)CrossRefGoogle Scholar
  18. 18.
    T. Ghosh, B.G. Maiya, A. Samanta, Dalton Trans. 795 (2006)Google Scholar
  19. 19.
    P. Kaur, D. Sareen, Dyes Pigm. 88, 296 (2011)CrossRefGoogle Scholar
  20. 20.
    C. Bhaumik, S. Das, D. Maity, S. Baitalik, Dalton Trans. 40, 11795 (2011)PubMedCrossRefGoogle Scholar
  21. 21.
    Z.-B. Zheng, Z.-M. Duana, J.-X. Zhanga, K.-Z. Wang, Sensor Actuat. B Chem. 169, 312 (2012)CrossRefGoogle Scholar
  22. 22.
    C. Bhaumik, D. Maity, S. Das, S. Baitalik, Polyhedron 52, 890 (2013)CrossRefGoogle Scholar
  23. 23.
    E.N. Shepelenko, V.A. Podshibyakin, Y.V. Revinskii, K.S. Tikhomirova, L.D. Popov, A.D. Dubonosov, I.N. Shcherbakov, V.A. Bren, V.I. Minkin, J. Mol. Struct. 1154, 219 (2018)CrossRefGoogle Scholar
  24. 24.
    I. Garcia, E. Bermejo, A.K.E. Sawaf, A. Castineiras, D.X. West, Polyhedron 21, 729 (2002)CrossRefGoogle Scholar
  25. 25.
    R. Pedrido, M.R. Bermejo, M.J. Romero, M. Vazquez, A.M.G. Noya, M. Maneiro, M.J. Rodriguez, M.I. Fernandez, Dalton Trans. 21, 572 (2005)CrossRefGoogle Scholar
  26. 26.
    C. Bhaumik, S. Das, D. Saha, S. Dutta, S. Baitalik, Inorg. Chem. 49, 5049 (2010)PubMedCrossRefGoogle Scholar
  27. 27.
    P. Mahato, S. Saha, A. Das, J. Phys. Chem. C 116, 17448 (2012)CrossRefGoogle Scholar
  28. 28.
    A. Mohammadi, M. Kianfar, J. Photochem. Photobiol. A Chem. 367, 22 (2018)CrossRefGoogle Scholar
  29. 29.
    M.S. Kumar, L.A. Kumar, A. Sreekanth, Anal. Methods 22, 6401 (2013)CrossRefGoogle Scholar
  30. 30.
    S.S. Sun, A.L. Lees, P.Y. Zavalij, Inorg. Chem. 42, 3445 (2013)CrossRefGoogle Scholar
  31. 31.
    L. Fabbrizzi, M. Licchelli, G. Rabaioli, A. Taglietti, Coord. Chem. Rev. 205, 85 (2000)CrossRefGoogle Scholar
  32. 32.
    C. Suksai, T. Tuntulani, Chem. Soc. Rev. 32, 192 (2003)PubMedCrossRefGoogle Scholar
  33. 33.
    M. Boiocchi, L.D. Boca, D.E. Gomez, L. Fabbrizzi, M. Licchelli, E. Monzani, J. Am. Chem. Soc. 126, 16507 (2004)PubMedCrossRefGoogle Scholar
  34. 34.
    D. Wu, T. Shao, J. Men, X. Chen, G. Gao, Dalton Trans. 43, 1753 (2014)PubMedCrossRefPubMedCentralGoogle Scholar
  35. 35.
    A. Mandal, A. Maity, S. Bag, P. Bhattacharya, A.K. Das, A. Basak, RSC Adv. 7, 7163 (2017)CrossRefGoogle Scholar
  36. 36.
    W.S. Tang, X.X. Lu, K.M. Wong, V.W. Yam, J. Mater. Chem. 15, 2714 (2005)CrossRefGoogle Scholar
  37. 37.
    D. Esteban-Gómez, L. Fabbrizzi, M. Licchelli, J. Org. Chem. 70, 5717 (2005)PubMedCrossRefPubMedCentralGoogle Scholar
  38. 38.
    V. Amendola, M. Boiocchi, L. Fabbrizzi, L. Mosca, Chem. Eur. J. 14, 9683 (2008)PubMedCrossRefGoogle Scholar
  39. 39.
    V. Amendola, L. Fabbrizzi, L. Mosca, Chem. Soc. Rev. 39, 3889 (2010)PubMedCrossRefGoogle Scholar
  40. 40.
    A. Okudan, S. Erdemir, O. Kocyigit, J. Mol. Struct. 1048, 392 (2013)CrossRefGoogle Scholar
  41. 41.
    I. Kieltsch, G.G. Dubinina, C. Hamacher, A. Kaiser, J.T. Nieto, J.M. Hutchinson, A. Klein, Y. Budnikova, D.A. Vicic, Organometallics 29, 1451 (2010)CrossRefGoogle Scholar
  42. 42.
    C. Suksai, P. Leeladee, D. Jainukan, T. Tuntulani, N. Muangsin, P. Chailapakul, O. Kongsaeree, C. Pakavatchai, Tetrahedron Lett. 46, 2765 (2005)CrossRefGoogle Scholar
  43. 43.
    A.R. Chowdhury, P. Ghosh, S.K. Saha, P. Mitra, P. Banerjee, Spectrochim. Acta. A 124, 492 (2014)CrossRefGoogle Scholar
  44. 44.
    A.R. Chowdhury, P. Ghosh, S. Paul, S. Bhuyan, J.C. Bose, S. Mukhopadhyay, P. Banerjee, Anal. Methods 9, 124 (2017)CrossRefGoogle Scholar
  45. 45.
    A. Mohammadi, Z. Dehghan, M. Rassa, N. Chaibakhsh, Sens. Actuators B Chem. 230, 388 (2016)CrossRefGoogle Scholar
  46. 46.
    A. Mohammadi, S. Khoshsoroor, B. Khalili, J. Photochem. Photobiol. A 384, 112035 (2019)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2020

Authors and Affiliations

  1. 1.Post-Graduate and Research Department of Chemistry, The New College (Autonomous)University of MadrasChennaiIndia

Personalised recommendations