Skip to main content
SpringerLink
Log in

Physicochemical Investigation of HDDP Azomethine Dye as Turn-On Fluorescent Chemosensor for High Selectivity and Sensitivity of Al3+ Ions

  • Published:
Journal of Solution Chemistry Aims and scope Submit manuscript

Abstract

4-[(2-Hydroxy-naphthalen-1-ylmethylene)-amino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one (HDDP) was synthesized by the reaction of 4-amino-1,5-dimethyl-2-phenyl-1,2-dihydro-3H-pyrazol-3-one with 2-hydroxy-l-naphthaldehyde. The structure was confirmed by the IR, 1H-NMR, 13C-NMR, and EI-MS spectra and elemental analysis. Physicochemical parameters of the HDDP such as extinction coefficient, oscillator strength, transition dipole moment, Stokes shift, and fluorescence quantum yield in different solvents were studied on the basis of polarities. The interactions of various metal ions with HDDP were also studied using steady state fluorescence measurements. The emission profile reveals that it acts as off–on type fluorescent chemosensor for selective and sensitive detection of Al3+ ions. Complexation stoichiometry and mechanism of enhancement were determined from a Benesi–Hildebrand plot.

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
Fig. 6
Fig. 7
Fig. 8: a
Fig. 9
Fig. 10
Fig. 11

Similar content being viewed by others

References

  1. Havrylyuk, D., Roman, O., Lesyk, R.: Synthetic approaches, structure activity relationship and biological applications for pharmacologically attractive pyrazole/pyrazoline–thiazolidine-based hybrids. Eur. J. Med. Chem. 113, 145–166 (2016)

    Article  CAS  Google Scholar 

  2. Asiri, A.M., Khan, S.A.: Synthesis, characterization, and in vitro antibacterial activities of macromolecules derived from bis-chalcone. J. Heterocycl. Chem. 49, 1434–1438 (2012)

    Article  CAS  Google Scholar 

  3. Nayak, N., Ramprasad, J., Dalimba, U., Yogeeswari, P., Sriram, D.: Synthesis and antimycobacterial screening of new N-(4-(5-aryl-3-(5-methyl-1,3,4-oxadiazol-2-yl)-1H-pyrazol-1-yl)phenyl)-4-amide derivatives. Chin. Chem. Lett. 27, 365–369 (2016)

    Article  CAS  Google Scholar 

  4. Kumar, V., Kaur, K.: Fluorinated isoxazolines and isoxazoles: a synthetic perspective. J. Fluorine Chem. 180, 55–97 (2015)

    Article  CAS  Google Scholar 

  5. Obasi, L.N., Kaior, G.U., Rhyman, L., Alswaidan, I.A., Ramasami, P.: Synthesis, characterization, antimicrobial screening and computational studies of 4-[3-(4-methoxy-phenyl)-allylideneamino]-1,5-dimethyl-2-phenyl-1,2-dihydro-pyrazol-3-one. J. Mol. Struct. 1120, 180–186 (2016)

    Article  CAS  Google Scholar 

  6. Steger, S., Matuszczak, B.: Synthesis of substituted 3-(3-chloro-1H-pyrazol-5-yl)quinoxalin-2(1H)ones. Tetrahedron 706, 763–6768 (2014)

    Google Scholar 

  7. Sztanke, K., Maziarka, A., Osink, A., Sztanke, M.: An insight into synthetic Schiff bases revealing antiproliferative activities in vitro. Bioorg. Med. Chem. 21, 3648–3666 (2013)

    Article  CAS  Google Scholar 

  8. Tan, X.J., Hao, X.Q., Zhao, Q.Z., Cheng, S.S., Song, L.Z.: Mono-Schiff-base or di-Schiff-base? Synthesis, spectroscopic, X-ray structural and DFT study of a series of Schiff-bases derived from benzil dihydrazone. J. Mol. Struct. 1099, 373–387 (2015)

    Article  CAS  Google Scholar 

  9. Khan, S.A., Asiri, A.M.: Physicochemical properties of novel methyl 2-{(E)-[(2-hydroxynaphthalen-1-yl)methylidene]amino}-4,5,6,7-tetrahydro-1-enzothiophene-3-carboxylate as turn-off fluorometric chemosensor for detection Fe3+ ion. J. Mol. Liq. 243, 85–90 (2017)

    Article  CAS  Google Scholar 

  10. Satam, M.A., Telore, R.D., Sekar, N.: Photophysical properties of Schiff’s bases from 3-(1,3-benzothiazol-2-yl)-2-hydroxynaphthalene-1-carbaldehyde. Spectrochim. Acta A 132, 678–686 (2014)

    Article  CAS  Google Scholar 

  11. Jia, J.H., Tao, X.M., Li, Y.J., Sheng, W.J., Zheng, Y.F.: Synthesis and third-order optical nonlinearities of ferrocenyl Schiff base. Chem. Phys. Lett. 514, 114–118 (2011)

    Article  CAS  Google Scholar 

  12. Cebeci, C., Kilicarslan, F.A., Gurbuz, O., Fırat, Y., Erden, I.: Synthesis and photovoltaic properties of organic photosensitizer using D-π-D type 4,5-diazafluorene ligand and derivatives for efficient dye-sensitized solar cell. Dyes Pigm. 134, 77–82 (2016)

    Article  CAS  Google Scholar 

  13. Sharbati, M.T., Rad, M.N.S., Behrouz, S., Gharavi, A., Emami, F.: Near infrared organic light-emitting diodes based on acceptor–donor–acceptor (ADA) using novel conjugated isatin Schiff bases. J. Lumin. 131, 553–558 (2011)

    Article  Google Scholar 

  14. Roy, N., Paul, P.C., Singh, T.S.: Fluorescence characteristics of Schiff base N,N-bis(salicylidene)trans1,2-diaminocyclohexane in the presence of bile acid host. J. Mol. Liq. 21, 1052–1059 (2015)

    Article  Google Scholar 

  15. Keshk, S.M.A.S., Ramadan, A.M., Bondock, S.: Physicochemical characterization of novel Schiff bases derived from developed bacterial cellulose 2,3-dialdehyde. Carbohydr. Polym. 127, 246–251 (2015)

    Article  CAS  Google Scholar 

  16. Kupeli, S.: Trace and rare-earth element behaviors during alteration and mineralization in the Attepe iron deposits (Feke-Adana, southern Turkey). J. Geochem. Explor. 105, 51–74 (2010)

    Article  Google Scholar 

  17. Fatemi, S.J.A., Kadir, F.H.A., Williamson, D.J., Moore, G.R.: The uptake, storage, and mobilization of iron and aluminum in biology. Adv. Inorg. Chem. 36, 409–448 (1991)

    Article  CAS  Google Scholar 

  18. Stah, T., Brunn, H.: Aluminium content of selected foods and food products. Environ. Sci. Eur. 2, 37–45 (2011)

    Article  Google Scholar 

  19. Ul Hassan, A., Hassan, G., Rasool, Z.: Role of stem cells in treatment of neurological disorder. Int. J. Health Sci. (Qassim) 3, 227–233 (2009)

    Google Scholar 

  20. Walton, J.R.: An aluminum-based rat model for Alzheimer’s disease exhibits oxidative damage, inhibition of PP2A activity, hyperphosphorylated tau, and granulovacuolar degeneration. J. Inorg. Biochem. 101, 1275–1284 (2007)

    Article  CAS  Google Scholar 

  21. Ren, J., Tian, H.: Thermally stable merocyanine form of photochromic spiropyran with aluminum ion as a reversible photodriven sensor in aqueous solution. Sensors 7, 3166–3178 (2007)

    Article  CAS  Google Scholar 

  22. Bencini, A., Lippolis, V.: Probing biologically and environmentally important metal ions with fluorescent chemosensors: thermodynamic versus optical response selectivity in some study cases. Coord. Chem. Rev. 256, 149–169 (2012)

    Article  CAS  Google Scholar 

  23. Sarkar, D., Ghosh, P., Gharami, S., Mondal, T.K., Murmu, N.: A novel coumarin based molecular switch for the sequential detection of Al3+ and F−: application in lung cancer live cell imaging and construction of logic gate. Sens. Actuators, B 242, 338–346 (2017)

    Article  CAS  Google Scholar 

  24. Liu, Y., Yang, E.B., Han, R., Zhang, D., Zhao, Y.F.: A new rhodamine-based fluorescent chemosensor for mercury in aqueous media. Chin. Chem. Lett. 25, 1065–1068 (2014)

    Article  CAS  Google Scholar 

  25. Chen, C., Liu, H., Zhang, B., Wang, Y., Jiang, Y.: A simple benzimidazole quinoline-conjugate fluorescent chemosensor for highly selective detection of Ag+. Tetrahedron 72, 3980–3985 (2016)

    Article  CAS  Google Scholar 

  26. Zheng, X., Lee, K.H., Liu, H., Park, S.Y., Kim, Y.G.: A bis(pyridine-2-ylmethyl) amine-based selective and sensitive colorimetric and fluorescent chemosensor for Cu2+. Sens. Actuators, B 222, 28–34 (2016)

    Article  CAS  Google Scholar 

  27. Asiri, A.M., Khan, S.A.: Synthesis, anti-bacterial activities of some novel Schiff bases derived from amino phenazone. Molecules 15, 6850–6858 (2010)

    Article  CAS  Google Scholar 

  28. Khan, S.A.: Green synthesis, spectrofluorometric characterization and antibacterial activity of heterocyclic compound from chalcone on the basis of in vitro and quantum chemistry calculation. J. Fluoresc. 27, 929–937 (2017)

    Article  CAS  Google Scholar 

  29. Wu, H., Chen, Y., Rao, C., Fan, D., Liu, C.: A selective fluorescent and colorimetric probe for cyanide based on dual-site controlled intramolecular charge transfer–photoinduced electron transfer fluorescence resonance energy transfer. Tetrahedron Lett. 57, 4969–4973 (2016)

    Article  CAS  Google Scholar 

  30. Suppan, P.: Invited review solvatochromic shifts: the influence of the medium on the energy of electronic states. J. Photochem. Photobiol., A 50, 293–330 (1990)

    Article  CAS  Google Scholar 

  31. Biradar, D.S., Siddlingeshwar, B., Hanagodimath, S.M.: Estimation of ground and excited state dipole moments of some laser dyes. J. Mol. Struct. 875, 108–112 (2008)

    Article  CAS  Google Scholar 

  32. Szczepanik, B., Styrcz, S., Gora, M.: Protolytic dissociation of cyanoanilines in the ground and excited state in water and methanol solutions. Spectrochim. Acta, Part A 71, 403–409 (2008)

    Article  Google Scholar 

  33. Mao, M., Xiao, S., Yi, T., Zou, K.: Synthesis and characterization of novel fluorescent BOPIM dyes with large Stokes shift. J. Fluorine Chem. 132, 612–616 (2011)

    Article  CAS  Google Scholar 

  34. Ganguly, P.: Photophysics of some cationic dyes in aqueous micellar dispersions of surfactants and in different solvents. J. Mol. Liq. 151, 67–73 (2010)

    Article  CAS  Google Scholar 

  35. Siddlingeshwar, B., Hanagodimath, S.M.: Estimation of first excited singlet-state dipole moments of aminoanthraquinones by solvatochromic method. Spectrochim. Acta A 72, 490–495 (2009)

    Article  CAS  Google Scholar 

  36. Climent, C., Carreras, A., Alemany, P., Casanova, D.: A push-pull organic dye with a quinoidal thiophene linker: photophysical properties and solvent effects. Chem. Phys. Lett. 663, 45–50 (2016)

    Article  CAS  Google Scholar 

  37. Khan, S.A., Asiri, A.M.: Fluorescence quenching of environmentally benign highly fluorescence donor (D)-π-acceptor (A)-π-donor (D) quinoline dye by silver nanoparticles and anionic surfactant in liquid stage. J. Mol. Liq. 221, 381–385 (2016)

    Article  CAS  Google Scholar 

  38. Reichardt, C.: Solvatochromic dyes as solvent polarity indicators. Chem. Rev. 94, 2319–2358 (1994)

    Article  CAS  Google Scholar 

  39. Zhou, D., Sun, C., Chen, C., Cui, X., Li, W.: Research of a highly selective fluorescent chemosensor for aluminum(III) ions based on photoinduced electron transfer. J. Mol. Struct. 1079, 315–320 (2015)

    Article  CAS  Google Scholar 

  40. Choi, Y.W., Lee, J.J., Nam, E., Lim, M.H., Kim, C.: A fluorescent chemosensor for Al3+ based on julolidine and tryptophan moieties. Tetrahedron 72, 1998–2005 (2016)

    Article  CAS  Google Scholar 

  41. Liao, Z.C., Yang, Z.Y., Li, Y., Wang, B.D., Zhou, Q.X.: A simple structure fluorescent chemosensor for high selectivity and sensitivity of aluminum ions. Dyes Pigm. 97, 124–128 (2013)

    Article  CAS  Google Scholar 

  42. Marwani, H.M., Asiri, A.M., Khan, S.A.: Spectral, stoichiometric ratio, physicochemical, polarity and photostability studies of newly synthesized chalcone dye in organized media. J. Lumin. 136, 296–302 (2013)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The authors are thankful to the Chemistry Department at King Abdulaziz University for providing research facilities.

Author information

Authors and Affiliations

  1. Chemistry Department, Faculty of Science, King Abdulaziz University, P.O. Box 80203, Jeddah, 21589, Saudi Arabia

    Abdullah M. Asiri, Tariq R. Sobahi, Mona Mohammad Al-Amari, Mohammad Asad, Mohie E. M. Zayed & Salman A. Khan

  2. Center of Excellence for Advanced Materials Research (CEAMR), King Abdulaziz University, P.O. Box 80203, Jeddah, 21589, Saudi Arabia

    Abdullah M. Asiri

Authors
  1. Abdullah M. Asiri
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Tariq R. Sobahi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Mona Mohammad Al-Amari
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Mohammad Asad
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Mohie E. M. Zayed
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. Salman A. Khan
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding authors

Correspondence to Abdullah M. Asiri or Salman A. Khan.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Asiri, A.M., Sobahi, T.R., Al-Amari, M.M. et al. Physicochemical Investigation of HDDP Azomethine Dye as Turn-On Fluorescent Chemosensor for High Selectivity and Sensitivity of Al3+ Ions. J Solution Chem 47, 1711–1724 (2018). https://doi.org/10.1007/s10953-018-0805-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-018-0805-1

Keywords

Search

Navigation