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Analysis of Fluorescence Quenching of Coumarin Derivative under Steady State and Transient State Methods

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Abstract

Nature has gifted us many organic molecules which have remarkable influence in our daily life. Amongst many organic molecules, heterocyclic organic molecules have gained potential applications in the advanced field of biomedicine, pharmaceutical, electronics and many more. In the present work fluorescence quenching of biologically active fluorescent probe 8EMOHCC by aniline in different solvents have been studied at room temperature. To understand the molecular behaviour in different media, solvents of different refractive index and dielectric constant have been used. Spectroscopic measurement techniques such as UV/Vis spectroscopy and time related single photon counting are employed to characterise the molecule at room temperature. The fluorescence quenching study shows linear dependence of SV-plot in solvents of different dielectric constants. It reveals that quenching reactions are dynamic in nature. Various parameters of quenching have been determined and identified the type of quenching involved in the quenching reaction. Further, kq is found to be greater than \( {k}_q^{\prime } \) in ACN, methanol, propanol and dioxane. Activation energy of quenching (Ea) is found to be greater than energy of diffusion (Ed) in ACN, methanol, propanol, THF solvents and Ed > Ea in dioxane, indicating that quenching reaction is not solely controlled by material diffusion but also activation process.

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The data provided in the manuscript is original one and are made available at any time on the request basis.

References

  1. Hoult JR, Paya M (1996) Pharmacological and biochemical actions of simple coumarins: natural products with therapeutic potential. General Pharmacology: The Vascular System 27:713–722

    Article  CAS  Google Scholar 

  2. Matos MJ, Vina D, Vazquez-Rodriguez S, Uriarte E, Santana L (2012) Focusing on new monoamine oxidase inhibitors: differently substituted coumarins as an interesting scaffold. Curr Top Medici Chem 12:2210–2239

    Article  CAS  Google Scholar 

  3. Matos J, Vazquez-Rodriguez S, Santana L, Uriarte E, Fuentes-Edfuf C, Santos Y, Muñoz-Crego A (2013) Synthesis and structure-activity relationships of novel amino/nitro substituted 3-Arylcoumarins as antibacterial agents. Molecules 18:1394–1404

    Article  CAS  Google Scholar 

  4. Morsy SA, Farahat AA, Nasr MNA, Tantawy AS (2017) Synthesis, molecular modeling and anticancer activity of new coumarin containing compounds. Saudi Pharmaceutical Journal 25:873–883

    Article  Google Scholar 

  5. Xia L, Wang Y, Huang W, Qian H (2013) Research advance of anticancer drugs with coumarin structures. Chinese Journal of New Drugs 22:2392–2404

    CAS  Google Scholar 

  6. Munir S, Shah AA, Shahid M, Ahmed MS, Shahid A, Rajoka MSR, Akash MSH, Akram M, Khurshid M (2020) Anti-angiogenesis potential of phytochemicals for the therapeutic Management of Tumors. Curr Pharm Des 25:265–278

    Article  Google Scholar 

  7. Song Y, Chen Z, Li H (2012) Advances in coumarin-derived fluorescent chemosensors for metal ions. Curr Org Chem 16:2690–2707

    Article  CAS  Google Scholar 

  8. Chen G, Li H, Lan R, Li J (2013) Research progress of coumarin-based fluorescent probes for ions of heavy and transition metals. Chemistry Bulletin 76:1002–1010

    CAS  Google Scholar 

  9. Melavanki RM, Kusanur RA, Kadadevaramath JS, Kulkarni M (2000) Effect of solvent polarity on the fluorescence quenching of biologically active 5BAMC by aniline in binary solvent mixtures. J Fluoresc 20:1175–1180

    Article  Google Scholar 

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

    Article  CAS  Google Scholar 

  11. Fujian Huang, Fan Xia (2018) Fluorescence sandwich assays for protein detection, biosensors based on sandwich assays, 29–45

  12. Wei H, Ruan J, Zhang X (2016) Coumarin-chalcone hybrids: promising agents with diverse pharmacological properties. RSC Adv:10215–11069

  13. Gao J, Qian G (2018) Design, synthesis and emerging applications of metal-organic frameworks. Curr Org Chem 22:1771–1772

    Article  CAS  Google Scholar 

  14. Salem. M. A, Helal. M. H, et.al (2018) An overview on synthetic strategies to coumarins, Synth Commun, 48: 1534–1550

  15. Raveendra. M. Melavanki, Raviraj. A. Kusanur, et.al (2010) Effect of solvent polarity on the fluorescence quenching of biologically active 5BAMC by aniline in binary solvent mixtures, J Fluoresec, 20: 1175–1180

  16. Bo A, Eng MP, Pettersson K, Winters MU (2007) Electron and energy transfer in donor–acceptor systems with conjugated molecular bridges. Phys Chem Chem Phys 44:5847–5864

    Google Scholar 

  17. Raghavendra UP, Mahantesha Basanagouda, Sidrai AH, Thipperudrappa J, (2016) Spectroscopic investigations on the interaction of biologically active 4-aryloxymethyl coumarins with TiO2 nanoparticles, 222: 601–608

  18. Wang Y, YanmeiLi TY (2020) Functionalized coumarin derivatives containing aromatic-imidazole unit as organic luminescent materials. Dyes Pigments 173:107958

    Article  CAS  Google Scholar 

  19. Patil O, Ingalagondi PK, Mathapati GB, Hanagodimath SM (2019) Analysis of fluorescence quenching of coumarin derivative dye using stern-Volmer plots. AIP Conference Proceedings 2142:180007

    Article  Google Scholar 

  20. Varsha V, Raveendra K, Melavanki M, Patil NR (2018) Solvent effect on the spectroscopic properties of 8EMOHCC. Materials Today: Proceedings 5:2781–2786

    Google Scholar 

  21. Lei Rong, Li-Han Liu, Si Chen, Han Cheng, et. al (2014) A coumarin derivative as a fluorogenic glycoproteomic probe for biological imaging. Chem Commun 50: 667–669

  22. Lackowicz JR (2006) Principles of fluorescence spectroscopy, 3rd edn. Plenum Press, New York

    Book  Google Scholar 

  23. Varsha V. Koppal, Raveendra M. Melavanki, Raviraj A. Kusanur and Ninganagouda. R. Patil (2018) Bimolecular fluorescence quenching reactions of the biologically active coumarin composite 2-acetyl-3H-benzo[f] chromen-3-one in different solvents, Luminescence, 1–7

  24. Nad S, Pal H (2000) Electron transfer from aromatic amines to excited coumarin dyes: fluorescence quenching and picosecond transient absorption studies. J Phys Chem A 104:673–680

    Article  CAS  Google Scholar 

  25. Koppal VV, Melavanki RM, Kusunur RA, Patil NR et al (2018) A role of solvent polarity on bimolecular quenching reactions of 3-acetyl-7-(diethylamino)-2H-chromen-2-one in binary solvent mixtures. J Mol Liq 260:221–228

    Article  CAS  Google Scholar 

  26. Suresh Kumar HM, Kunabenchi RS, Biradar JS, Math NN, Kadadevarmath JS, Inamdar SR (2006) Analysis of fluorescence quenching of new indole derivative by aniline using stern–Volmer plots. Journal Luminescence 116:35–42

    Article  CAS  Google Scholar 

  27. Creaven BS, Egan DA, Kavanagh K, McCann M, Noble A, Thati B, Walsh M (2006) Synthesis, characterization and antimicrobial activity of a series of substituted coumarin-3-carboxylatosilver(I) complexes. Inorg Chim Acta 359:3976–3984

    Article  CAS  Google Scholar 

  28. Kusanur RA, Ghate M, Kulkarni MV (2004) Synthesis of spiro[indolo-1,5-benzodiazepines] from 3-acetyl coumarins for use as possible antianxiety agents. J Chem Sci 116:265–270

    Article  CAS  Google Scholar 

  29. Nagaraja D, Melavanki RM, Patil NR (2013) Fluorescence quenching of 6BDTC by aniline in different solvents. Can J Phys 91:966–970

    Article  CAS  Google Scholar 

  30. Koppal VV, Patil PG, Melavanki RM, Kusanur RA, Patil NR (2019) Solvent effect on the relative quantum yield and preferential solvation of biologically active Coumarin derivative. Macromol Symp 387:1800210–1800212

    Article  CAS  Google Scholar 

  31. Patil NR, Melavanki RM, Kapatkar SB, Chandrashekhar K, Umapathy S et al (2011) Fluorescence quenching of biologically active carboxamide by aniline and carbon tetrachloride in different solvents using Stern–Volmer plots. Spectrochim Acta A Mol Biomol Spectrosc 79:1985–1991

    Article  CAS  Google Scholar 

  32. Andre JC, Niclause M, Ware WR (1978) Kinetics of partly diffusion controlled reactions. I. Transient and apparent transient effect in fluorescence quenching. Chemical Physics 28:371–377

    Article  CAS  Google Scholar 

  33. Wilemski G, Fixman M (1973) General theory of diffusion-controlled reactions. J Chem Phys 58:4009–4019

    Article  CAS  Google Scholar 

  34. Yguerabide J, Dillon MA, Burton M (1964) Kinetics of diffusion-controlled processes in liquids. Theoretical consideration of luminescent systems: quenching and excitation transfer in collision. Journal of Chemical Physics 40:3040–3052

    Article  CAS  Google Scholar 

  35. Einstein. A, Investigations on the theory of Brownian movment, Dover New York, 1956. 103

  36. Sanniningannavar FM, Navathi BS, Nagaraja D, Patil NR, Melavanki RM (2015) Quenching mechanism of 5BDTC by aniline using S-V plots. Can J Phys 93:1076–1081

    Article  Google Scholar 

  37. Edward JT (1970) Molecular volumes and the stokes-Einstein equation. J Chem Educ 47:261–270

    Article  CAS  Google Scholar 

  38. Sharma VK, Mohan D, Sahare PD (2007) Fluorescence quenching of 3-methyl-7-hydroxyl coumarin in presence of acetone. Spectrochim Acta A 66:111–113

    Article  Google Scholar 

  39. Williamson B, La Mer VK (1948) The kinetics of activation-diffusion controlled reactions in solution; the temperature dependence of the quenching of fluorescence. Journal of American Chemical Society 70:717–721

    Article  CAS  Google Scholar 

  40. Koppal VV, Melavanki RM, Kusanur RA, Patil NR (2018) Understanding fluorescence resonance energy transfer between biologically active coumarin derivative and silver nanoparticles using steady state and time resolved spectroscopic methods. J Mol Liq 269:381–386

    Article  CAS  Google Scholar 

  41. Keizer J (1985) Additions and corrections - nonlinear fluorescence quenching and the origin of positive curvature in stern-Volmer plots. Journal of American Chemical Society 107:5319–5319

    Article  Google Scholar 

  42. Keizer J (1987) Diffusion effects on rapid bimolecular chemical reactions. Chem Rev 87:167–180

    Article  CAS  Google Scholar 

  43. Thipperudrappa J et al (2006) Fluorescence quenching of BPBD by aniline in benzene–acetonitrile mixtures. J Photochem Photobiol A Chem 177:89–93

    Article  CAS  Google Scholar 

Download references

Acknowledgements

This research work is supported by KLE Technological University under “Capacity Building Projects” grants. The author V. V. Koppal thanks the Management, KLE Society Belgaum for financial support. The author Raveendra Melavanki acknowledges the Principal, MSRIT and the Management, Gokul Education Society for encouragement.

Funding

The Authors have no major funding from any scientific agencies but we have funded by institute as Capacity Building Fund to meet out the expenses to purchase materials and various measurements.

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Authors and Affiliations

  1. Department of Physics, KLE Technological University, Hubli, Karnataka, 580031, India

    V. V. Koppal

  2. Department of Physics, M S Ramaiah Institute of Technology, Bangalore, Karnataka, 560054, India

    Raveendra Melavanki

  3. Department of Chemistry, R.V. College of Engineering, Bangalore, Karnataka, 560059, India

    Raviraj Kusanur

  4. Department of Physics, B V B College of Engineering and Technology, Hubli, Karnataka, 580031, India

    N. R. Patil

  5. Visvesvaraya Technological University, -590018, Belgaum, Karnataka, India

    Raveendra Melavanki, Raviraj Kusanur & N. R. Patil

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  1. V. V. Koppal
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  3. Raviraj Kusanur
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Contributions

V. V. Koppal: Performed Experimental part and prepared manuscript.

Raveendra Melavanki: Contributed valuable discussions to the results and discussions.

Raviraj Kusanur: Synthesis of title molecule and helped in the analysis of NMR Spectra.

N R Patil: Corrected the Experimental part and manuscript.

Corresponding author

Correspondence to N. R. Patil.

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This to certify that the article entitled “Analysis of fluorescence quenching of coumarin derivative under steady state and transient state methods” submitted by V.V. Koppal et al., for the publication in Journal of Fluorescence is based on the original work and results of the experiments were carried out by all authors under my supervision. No part of the article has been previously submitted for the publication in any journals. There are no any issues of conflict of authors of the manuscript.

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Koppal, V.V., Melavanki, R., Kusanur, R. et al. Analysis of Fluorescence Quenching of Coumarin Derivative under Steady State and Transient State Methods. J Fluoresc 31, 393–400 (2021). https://doi.org/10.1007/s10895-020-02663-3

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  • DOI: https://doi.org/10.1007/s10895-020-02663-3

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