Skip to main content
Log in

Study of Fluorescence Quenching on Novel Coumarin Derivatives by Aniline in Different Solvents

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

Abstract

The steady-state fluorescence quenching of novel coumarin derivatives; 4-(2, 6-dibromo-4-methyl-phenoxymethyl)-benzo[h]chromen-2-one [DMB] and 6-methoxy-4-p-tolyoxymethyl-chromen-2-one [TMC] has been studied in toluene, benzene, dioxane, acetonitrile and tetrahydrofuran [THF] using aniline as a quencher at room temperature with a view to understanding the role of diffusion in the quenching mechanism. The probability of quenching per encounter (p) is calculated in all the solvents. Further, an activation energy for quenching (E a) was estimated using the values of p and the literature values of activation energy for diffusion (E d). The magnitudes of these parameters indicate that the fluorescence quenching of these molecules by aniline is not solely due to the material diffusion but there is also a contribution of an activation energy.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Subscribe and save

Springer+ Basic
$34.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or eBook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Fig. 1
Fig. 2
Fig. 3
Fig. 4

Similar content being viewed by others

References

  1. Behera, P.K., Mishra, A.K.: Static and dynamic model for 1-naphthol fluorescence quenching by carbon tetrachloride in dioxane–acetonitrile mixtures. J. Photochem. Photobiol. A: Chem. 71, 115–118 (1993)

    Article  CAS  Google Scholar 

  2. Desai, V.R., Hunagund, S.M., Basanagouda, M., Kadadevarmath, J.S., Thipperudrappa, J., Sidarai, A.H.: Spectroscopic studies on newly synthesised 5-(2-hydroxy-5-methoxy-phenyl)-2-phenyl-2H-pyridazin-3-one molecule. J. Mol. Liq. 225, 613–620 (2016)

    Article  Google Scholar 

  3. Olmsted, J.: Oxygen quenching of fluorescence of organic dye molecules. J. Chem. Phys. Lett. 26, 33–36 (1974)

    Article  CAS  Google Scholar 

  4. Schizuka, H., Saito, T., Morita, T.: Fluorescence quenching of aromatic molecules by inorganic anions. J. Chem. Phys. Lett. 56, 519–522 (1978)

    Article  Google Scholar 

  5. Desai, V.R., Hunagund, S.M., Pujar, M.S., Basanagouda, M., Kadadevarmath, J.S., Sidarai, A.H.: Spectroscopic interactions of titanium dioxide nanoparticles with pharmacologically active 3(2H)-pyridazinone derivative. J. Mol. Liq. 233, 166–172 (2017). doi:10.1016/j.molliq.2017.03.018

    Article  CAS  Google Scholar 

  6. Mortazavi, M.A., Kowel, S.T., Henry, R., Hoover, A., Lindsay, G.A.: Second-order nonlinear optical properties of poled coumaromethacrylate copolymers. Appl. Phys. B: Lasers Opt. 53, 287–295 (1991)

    Article  Google Scholar 

  7. Duarte, F.J., Hillman, L.W.: Dye Laser Principles with Applications. Academic Press Inc., San Diego (1990)

    Google Scholar 

  8. Kohjiro, H., Dan-oh, Y., Kasada, C., Shinpo, A., Suga, S., Sayama, K., Arakawa, H.: Design of new coumarin dyes having thiophene moieties for highly efficient organic-dye-sensitized solar cell. New J. Chem. 27, 783–785 (2003)

    Article  Google Scholar 

  9. Mishra, A.: Metal-free organic dyes for dye-sensitized solar cells: from structure: property relationships to design rules. Chem. Int. Ed. 48, 2474–2499 (2009)

    Article  CAS  Google Scholar 

  10. Zhao, H., Hong, N., Mazumder, H., Wang, A., Sunder, S., Milne, S.G., Pommier, Y., Burke, T.R.: Hydrazide-containing inhibitors of HIV-1 integrase. J. Med. Chem. 40, 242–249 (1997)

    Article  CAS  Google Scholar 

  11. Kontogiorgis, C., Hadjipavlou, D.: Biological evaluation of several coumarin derivatives designed as possible anti-inflammatory/antioxidant agents. J. Enzym. Inhib. Med. Chem. 18, 63–69 (2003)

    Article  CAS  Google Scholar 

  12. Basanagouda, M., Kulkarni, M.V., Sharma, D., Gupta, V.K., Pranesha, P.: Sandhyarani, Rasal, V.P.: synthesis of some new 4-aryloxymethylcoumarins and examination of their antibacterial and antifungal activities. J. Chem. Sci. 121, 485–495 (2009)

    Article  CAS  Google Scholar 

  13. Basanagouda, M., Jambagi, V.B., Barigidad, N.N., Laxmeshwar, S.S., Devaru, V.: Narayanachar: synthesis, structure activity relationship of iodinated-4-aryloxymethyl-coumarins as potential anti-cancer and antimycobacterial agents. Eur. J. Med. Chem. 74, 225–233 (2014)

    Article  CAS  Google Scholar 

  14. Sidarai, A.H., Desai, V.R., Hunagund, S.M., Basanagouda, M., Kadadevarmath, J.S.: Effect of solvent polarity on the fluorescence quenching of TMC molecule by aniline in benzene–acetonitrile mixtures. Can. J. Phys. 94, 1125–1132 (2016)

    Article  CAS  Google Scholar 

  15. Basanagouda, M.: Synthesis of some new 4-aryloxmethylcoumarins and examination of their antibacterial and antifungal activities. J. Chem. Sci. 121, 485–495 (2009)

    Article  CAS  Google Scholar 

  16. Einstein, A.: Investigations on the Theory of Brownian Movement. Dover, New York (1956)

    Google Scholar 

  17. Kadadevarmath, J.S., Giraddi, T.P., Malimath, G.H., Chikkur, G.C.: Electronic excitation energy quenching of an organic liquid scintillator by carbon tetrachloride in different solvents. J. Radiat. Meas. 26, 117–118 (1996)

    Article  CAS  Google Scholar 

  18. Edward, J.T.: Molecular volumes and the Stokes–Einstein equation. J. Chem. Edu. 47, 261 (1970)

    Article  CAS  Google Scholar 

  19. Biradar, D.S., Thipperudrappa, J., Hanagodimath, S.M.: Fluorescence quenching studies of 1,3-diphenyl benzene. Spectrosc. Lett. 40, 559–571 (2007)

    Article  CAS  Google Scholar 

  20. Melavanki, R.M., Patil, N.R., Patil, H.D., Kusanur, R.A., Kadadevaramath, J.S.: Fluorescence quenching of 1, 4-bis [2-(2-methyl phenyl) ethenyl]-benzene by aniline in benzene–acetonitrile. Indian J. Pure Appl. Phys. 49, 748–753 (2011)

    CAS  Google Scholar 

Download references

Acknowledgements

Authors are grateful to the technical staff of USIC, Karnatak University Dharwad for recording absorption spectra, fluorescence spectra and fluorescence lifetimes measurements.

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Ashok H. Sidarai.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Sidarai, A.H., Desai, V.R., Hunagund, S.M. et al. Study of Fluorescence Quenching on Novel Coumarin Derivatives by Aniline in Different Solvents. J Solution Chem 46, 1328–1336 (2017). https://doi.org/10.1007/s10953-017-0645-4

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10953-017-0645-4

Keywords

Navigation