2-(4,5-Dimethyl-1-m-tolyl-1H-imidazol-2-yl)phenol as Efficient Chemosensor for On–Off Fluorescence System: Catalytic Synthesis and NMR Spectral Studies

  • T. S. Rajasekar
  • P. Navamani
  • K. Jayamoorthy
  • N. Srinivasan
Article
First Online:
Received:
Accepted:

Abstract

An efficient chemosensor 2-(4,5-dimethyl-1-m-tolyl-1H-imidazol-2-yl)phenol (DMTP) has been designed and synthesized using nano SiO2 as catalyst. Nano SiO2 exhibited remarkable catalytic activity with respect to the reaction time, amount of catalyst and vast range of substrates usage. Synthesized compounds have been characterized by 1H and 13C-NMR spectral studies. Proton and 13C chemical shift of the synthesized compounds have been calculated. DMTP has been used to construct highly sensitive fluorescent chemosensor for sensing of metal ions. It can behave as a selective fluorescent sensor for the detection of Fe3+ metal ion. Addition and increasing concentration of Fe3+ ions into DMTP results excellent fluorescence quenching. Other cations, including Ca2+, Al3+, K+, Cd2+, Pb2+, Zn2+ and Mg2+ had little influence in the fluorescence intensity. Surprisingly reversible fluorescence enhancement has been observed with the addition of H3PO4 due to the deactivation of iron complex.

Keywords

Chemosensor Fluorescence Nano SiO2 Chemical shift 
This is a preview of subscription content, log in to check access.

Notes

Acknowledgements

One of the Author Dr. N. Srinivasan gratefully acknowledge the Chairman, Secretary and Trust board members, Pachaiyappa’s trust board, Harrington Road, Chennai—600030 for providing necessary facilities to do this research work in a successive manner.

References

  1. 1.
    S. Suresh, S. Karthikeyan, P. Saravanan, K. Jayamoorthy, K.I. Dhanalekshmi, Comparison of antibacterial and antifungal activity of 5-amino-2-mercapto benzimidazole and functionalized Ag3O4 nanoparticles, Karbala International. J. Mod. Sci. 2, 129–137 (2016)Google Scholar
  2. 2.
    J. Jayabharathi, V. Thanikachalam, K. Jayamoorthy, J. Photochem. Photobiol. B 115, 85–92 (2012)CrossRefGoogle Scholar
  3. 3.
    B. Valeur, I. Leray, Coord. Chem. Rev 205, 3–40 (2000)CrossRefGoogle Scholar
  4. 4.
    S.M. Prakash, K. Jayamoorthy, N. Srinivasan, T.S. Rajasekar, B. Subash, Nano-SiO2: An efficient catalyst for the synthesis of some new benzimidazoles-NMR spectral characterization. Silicon (2017). doi: 10.1007/s12633-016-9500-2 Google Scholar
  5. 5.
    K. Boonkitpatarakul, J. Wang, N. Niamnont, B. Liu, L. Mcdonald, Y. Pang, M. Sukwattanasinitt, ACS Sens. (2016), 1, 144–150Google Scholar
  6. 6.
    J. Jayabharathi, K. Jayamoorthy, V. Thanikachalam, Synthesis, photophysical and electroluminescent properties of green organic light emitting devices based on novel iridium complexes containing benzimidazole ligands. J. Organomet. Chem. 761, 74–83 (2014)CrossRefGoogle Scholar
  7. 7.
    B. D’Autreaux, N.P. Tucker, R. Dixon, S. Spiro, Nature 437, 769–772 (2005)CrossRefGoogle Scholar
  8. 8.
    J.W. Lee, J.D. Helmann, Nature 440, 363–367 (2006)CrossRefGoogle Scholar
  9. 9.
    H. Weizman, O. Ardon, B. Mester, J. Libman, O. Dwir, Y. Hadar, Y. Chen, A. Shanzer, J. Am. Chem. Soc. 118, 12368–12375 (1996)CrossRefGoogle Scholar
  10. 10.
    H. Xu, Z. Liu, L. Sheng, M. Chen, D. Huang, H. Zhang, C. Song, S. Chen, New J. Chem. 37, 274 (2013)CrossRefGoogle Scholar
  11. 11.
    J.V. Mello, N.S. Finney, J. Am. Chem. Soc. 127, 10124 (2005)CrossRefGoogle Scholar
  12. 12.
    C. Karunakaran, J. Jayabharathi, K. Jayamoorthy, P. Vinayagamoorthy, Inhibition of fluorescence enhancement of benzimidazole derivative on doping ZnO with Cu and Ag. J. Photochem. Photobiol. A 247, 16–23 (2012)CrossRefGoogle Scholar
  13. 13.
    C. Karunakaran, J. Jayabharathi, K. Jayamoorthy, K.B. Devi, Sensing rutile TiO2 through fluorescence of imidazole derivative. Sens. Actuators B 168, 263–270 (2012)CrossRefGoogle Scholar
  14. 14.
    P. Saravanan, K. Jayamoorthy, S.A. Kumar, Switch-on fluorescence and photo-induced electron transfer of 3-aminopropyltriethoxysilane to ZnO: dual applications in sensors and antibacterial activity. Sens. Actuators B 221, 784–791 (2015)CrossRefGoogle Scholar
  15. 15.
    C. Karunakaran, J. Jayabharathi, K.B. Devi, K. Jayamoorthy, Photosensitization of imidazole derivative by ZnO nanoparticle. J Fluoresc 22(4), 1047–1053 (2012)CrossRefGoogle Scholar
  16. 16.
    C. Karunakaran, J. Jayabharathi, K. Jayamoorthy, Fluorescence enhancing and quenching of TiO2 by benzimidazole. Sens. Actuators B 188, 207–211 (2013)CrossRefGoogle Scholar
  17. 17.
    C. Karunakaran, J. Jayabharathi, K. Jayamoorthy, Photo-induced electron transfer from benzimidazole to nano WO3, CuO and Fe2O3. A new approach on LUMO–CB energy-binding efficiency relationship. Sens. Actuators B 182, 514–520 (2013)CrossRefGoogle Scholar
  18. 18.
    C. Karunakaran, J. Jayabharathi, R. Sathishkumar, K. Jayamoorthy, Interaction of fluorescent sensor with superparamagnetic iron oxide nanoparticles. Spectrochim. Acta Part A. 110, 151–156 (2013)CrossRefGoogle Scholar
  19. 19.
    C. Karunakaran, J. Jayabharathi, R. Sathishkumar, K. Jayamoorthy, Contrasting emission behavior of phenanthroimidazole with rutile and anatase TiO2 nanoparticles. J. Lumin. 138, 235–241 (2013)CrossRefGoogle Scholar
  20. 20.
    J. Jayabharathi, V. Thanikachalam, M. Vennila, K. Jayamoorthy, DFT based ESIPT process of luminescent chemosensor: taft and Catalan solvatochromism. Spectrochim. Acta Part A 95, 589–595 (2012)CrossRefGoogle Scholar
  21. 21.
    C. Karunakaran, J. Jayabharathi, K. Jayamoorthy, Benzimidazole: dramatic luminescence turn-on by ZnO nanocrystals. Measurement 46(10), 3883–3886 (2013)CrossRefGoogle Scholar
  22. 22.
    C. Karunakaran, J. Jayabharathi, K. Jayamoorthy, Fluorescence quenching of organic molecule by insulator. Spectrochim. Acta Part A Mol. Biomol. Spectrosc. 112, 417–421 (2013)CrossRefGoogle Scholar
  23. 23.
    S.M. Prakash, K. Jayamoorthy, N. Srinivasan, K.I. Dhanalekshmi, Fluorescence tuning of 2-(1H-Benzimidazol-2-yl) phenol-ESIPT process. J. Lumin. 172, 304–308 (2016)CrossRefGoogle Scholar
  24. 24.
    S. Suresh, S. Karthikeyan, P. Saravanan, K. Jayamoorthy, Comparison of antibacterial and antifungal activities of 5-amino-2-mercaptobenzimidazole and functionalized NiO nanoparticles, Karbala International. J. Mod. Sci. 2(3), 188–195 (2016)Google Scholar
  25. 25.
    P. Saravanan, K. Jayamoorthy, S.A. Kumar, Eco-Friendly Nano-Hybrid Materials for Advanced Engineering Applications, Apple Academic Press, Oakville 263–280Google Scholar
  26. 26.
    V. Kalaiarasi, R. Francis Nicholas Ashok, M. Prabakaran, R. Paulsingh, Fluorescence Enhancement performance of 1-(4-fluorophenyl)-2- (naphthalen-1-yl)-4, 5-diphenyl-1H-imidazole[FNDI] bound Fe2O3 nanoparticles. DJ J. Eng Chem Fuel 2(1), 50–60 (2017)CrossRefGoogle Scholar
  27. 27.
    T. Pazhalanisamy, P. Ramanathan, G. Sujatha, V. Anusuya, G.L. Balaji, Binding interaction and optical properties of 1-(4-methoxyphenyl)-2- (naphthalen-1-yl)-1H-phenanthro [9,10-d]imidazole with ZnO nanoparticle. DJ J. Eng Chem. Fuel 2(1), 41–49 (2017)CrossRefGoogle Scholar
  28. 28.
    S.M. Prakash, S. Mohan, T.S. Rajasekar, N. Srinivasan, Fluorescence report on the binding interaction of imidazole using bovine serum Albumin. DJ J. Eng Chem. Fuel 2(1), 21–29 (2017)CrossRefGoogle Scholar
  29. 29.
    R. Jayaseelan, M. Gopalakrishnan, Binding interaction study of 5-(difluoromethoxy)-2-Mercapto-1HBenzimidazole along with BaTiO3 nanoparticle. DJ J. Eng. Chem. Fuel 2(1), 1–9 (2017)CrossRefGoogle Scholar
  30. 30.
    P. Kakkar, B. Madhan, Mater. Sci Eng C 66, 178–184 (2016)CrossRefGoogle Scholar
  31. 31.
    A.S. Timin, S.Y. Khashirova, E.V. Rumyantsev, A.A. Goncharenko, Mater Sci Eng: C, 64,, 20–28 (2016)CrossRefGoogle Scholar
  32. 32.
    C. Karunakaran, J. Jayabharathi, K. Jayamoorthy, K.B. Devi, Photoinduced electron-transfer from imidazole derivative to nano-semiconductors. Spectrochim. Acta A 89, 187–193 (2012)CrossRefGoogle Scholar
  33. 33.
    J. Jayabharathi, V. Thanikachalam, K. Jayamoorthy, Synthesis of some fluorescent benzimidazole derivatives using cobalt hydroxide (II) as high efficient catalyst—spectral, physico-chemical studies and ESIPT process. Photochem. Photobiol. Sci 12, 1761–1773 (2013)CrossRefGoogle Scholar
  34. 34.
    K. Jayamoorthy, T. Mohandas, P. Sakthivel, J. Jayabharathi, 1-Phenyl-2-[4-(trifluoromethyl)phenyl]1H-benzimidazole. Acta Cryst. 69, o244 (2013)Google Scholar
  35. 35.
    J. Jayabharathi, K. Jayamoorthy, V. Thanikachalam, Lifetime time measurements, Kamlet-Taft and catalan solvatochromism of some 2-aryl benzimidazole derivatives. Spectrochim. Acta Part A 101 156–161 (2013)CrossRefGoogle Scholar
  36. 36.
    J. Jayabharathi, V. Thanikachalam, K. Jayamoorthy, N. Srinivasan, Synthesis, spectral studies and solvatochromism of some novel benzimidazole derivatives—ESIPT process. Spectrochim. Acta Part A 105, 223–228 (2013)CrossRefGoogle Scholar
  37. 37.
    R. Krämer, Fluorescent chemosensors for Cu2+ ions: fast, selective, and highly sensitive. Angew Chem Int Ed 37, 772–773 (1998)CrossRefGoogle Scholar
  38. 38.
    G. Sivaraman, D. Chellappa, Rhodamine based sensor for naked-eye detection and live cell imaging of fluoride ions. J Mater Chem B 1, 5768–5772 (2013)CrossRefGoogle Scholar
  39. 39.
    A. Kumar, H.-S. Kim, N-(3-imidazolyl)propyl dansylamide as a selective Hg2 + sensor in aqueous media through electron transfer. Spectrochim. Acta A 148, 250–254 (2015)CrossRefGoogle Scholar
  40. 40.
    Z.Y. Li, Y. Lin, J.L. Xia, H. Zhang, F.Y. Fan, Q.B. Zeng, Dyes Pigments, 90, 2011, 245–252CrossRefGoogle Scholar

Copyright information

© Springer Science+Business Media New York 2017

Authors and Affiliations

  • T. S. Rajasekar
    • 1
    • 2
  • P. Navamani
    • 1
    • 3
  • K. Jayamoorthy
    • 4
  • N. Srinivasan
    • 1
    • 5
  1. 1.Research and Development CenterBharathiar UniversityCoimbatoreIndia
  2. 2.Department of ChemistryS.K.P Engineering CollegeThiruvanamalaiIndia
  3. 3.Department of ChemistryThiruvalluvar College of Engineering and TechnologyVandavasiIndia
  4. 4.Department of ChemistrySt.Joseph’s College of EngineeringChennaiIndia
  5. 5.Department of ChemistryPachaiyappa’s College for MenKanchipuramIndia

Personalised recommendations