Abstract
The effect of position of benzo group in coumarin derivatives, 5,6 benzo-4-azidomethyl coumarin (5BAMC) and 7,8 benzo-4-azidomethyl coumarin (7BAMC) during their interaction with TiO2 nanoparticles in ethyl acetate, tetrahydrofuran, butan-1-ol and acetonitrile solvents has been studied using different spectroscopic methods and electrochemical analysis. Benesi-Hildebrand plots indicate that nature of interaction between 7BAMC and TiO2 is 1:2 in solvent with low dielectric constant whereas for 5BAMC and TiO2, it is 1:1 in all the solvents. From the fluorescence quenching study and binding equilibria analysis, it is observed that interaction between 5BAMC and TiO2 depends on the dielectric constant of the solvent. Time resolved quenching study reveals that quenching is dynamic for 5BAMC in solvent with high dielectric constant. Whereas for 7BAMC, it is dynamic in solvent with low dielectric constant. Hence the nature of interaction of these two coumarin derivatives with TiO2 NPs is different. From electrochemical analysis, it is observed that, free energy change for electron transfer is more negative for 5BAMC-TiO2 compared to 7BAMC-TiO2 therefore quenching is more efficient for 5BAMC-TiO2 compared to 7BAMC-TiO2 system, which is also confirmed from fluorescence quenching studies. Non-radiative energy transfer rate is more than radiative energy transfer rate for both the systems according to FRET study.
Similar content being viewed by others
References
Ziental D, Czarczynska-Goslinska B, Mlynarczyk DT, Glowacka-Sobotta A, Stanisz B, Goslinski T, Sobotta L (2020) Titanium dioxide nanoparticles: prospects and applications in medicine. Nanomaterials 10:387. https://doi.org/10.3390/nano10020387
Youssef Z, Vanderesse R, Colombeau L, Baros F, Roques-Carmes T, Frochot C, Wahab H, Toufaily J, Hamieh T, Acherar S, Gazzali AM (2017) The application of titanium dioxide, zinc oxide, fullerene, and graphene nanoparticles in photodynamic therapy. Cancer nanotechnology 8:6. https://doi.org/10.1186/s12645-017-0032-2
Khan I, Saeed K, Khan I (2019) Nanoparticles: properties, applications and toxicities. Arab J Chem 12(7):908–931
Kathiravan A, Asha Jhonsi M, Renganathan R (2011) Photo induced interaction of colloidal TiO2 nanoparticles with lysozyme: evidences from spectroscopic studies. J Lumin 131:1975–1981
Kathiravan A, Renganathan R (2008) Interaction of colloidal TiO2 with bovine serum albumin: a fluorescence quenching study. Colloids and Surfaces A: Physicochem Eng Aspects 324:176–180
Sun W, Yingxiang D, Chen J, Kou J, Yu B (2009) Interaction between titanium dioxide nanoparticles and human serum albumin revealed by fluorescence spectroscopy in the absence of photo activation. J Lumin 129:778–783
Chougala LS, Kadadevarmath JS, Kamble AA, Torvi AI, Yatnatti MS, Nirupama JM, Kamble RR (2018) Spectroscopic investigations of interaction between TiO2 and newly synthesized phenothiazine derivative-PTA dye and its role as photosensitizer. J Lumin 198:117–123
Chougala LS, Kadadevarmath JS, Kamble AA, Bayannavar PK, Yatnatti MS, Linganagoudar RK, Nirupama JM, Kamble RR, Qiao Q (2017) Effect of TiO2 nanoparticles on newly synthesized phenothiazine derivative-CPTA dye and its applications as dye sensitized solar cell. J Mol Liq 244:97–102
Raghavendra UP, Mahantesha B, Sidrai AH, Thipperudrappa J (2016) Spectroscopic investigations on the interaction of biologically active 4-aryloxymethyl coumarins with TiO2 nanoparticles. J Mol Liq 222:601–608
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
Mahantesha B, Shivashankar K, Kulkarni MV, Rasal VP, Patel H, Mutha SS, Mohite AA (2010) Synthesis and antimicrobial studies on novel sulfonamides containing 4-azidomethyl coumarin. Eur J Med Chem 45:1151–1157
Wagner BD (2009) The Use of Coumarins as Environmentally-Sensitive Fluorescent Probes of Heterogeneous Inclusion Systems. Molecules 14:210–237. https://doi.org/10.3390/molecules14010210
Kaholek M, Hrdlovi P (1997) Spectral properties of coumarin derivatives substituted at position 3. Effect of polymer matrix J. Photochem. Photobio. A: Chem. 108:283–288
Latesh T, Sharma AK, Singh RD (1995) Study of photophysical properties of Coumarins: substituent and concentration dependence. J Lumin 63:203–214
Melavanki RM, Patil NR, Kapatkar SB, Ayachit NH, Siva U, Thipperudrappa J, Nataraju AR (2011) Solvent effect on the spectroscopic properties of 6MAMC and 7MAMC. J Mol Liq 158:105–110
Nirupama JM, Khanapurmath NI, Chougala LS, Kulkarni MV, Kadadevarmath JS (2019) Effect of stereo electronic factors of coumarin derivatives during their interaction with TiO2 nanoparticles. J Mol Liq 291:111266
Szatylowicz H, Siodla T, Stasyuka OA, Krygowski TM (2016) Towards physical interpretation of substituent effects: the case of meta- and Para-substituted anilines Phys. Chem Chem Phys 18:11711–11721
Nirupama JM, Khanapurmath NI, Chougala LS, Shastri LA, Bhajantri RF, Kulkarni MV, Kadadevarmath JS (2019) Effect of amino anilines on the fluorescence of coumarin derivative. J Lumin 208:164–173
Nirupama JM, Chougala LS, Khanapurmath NI, Ashish A, Shastri LA, Kulkarni MV, Kadadevarmath JS (2017) Fluorescence investigations on interactions between 7,8-benzo-4- azidomethyl Coumarin and Ortho and Para-phenylenediamines in binary solvent mixtures of THF and water. J Fluoresce 28:359–372. https://doi.org/10.1007/s10895-017-2198-8
Kusanur RA, Kulkarni MV (2003) Ind. Counc. Chem. 22nd Conference Roorkee 00–29
Valeur B (2001) Molecular fluorescence: principles and applications. Wiley-VCH Verlag GmbH
Benesi HA, Hildebrand JH (1949) A spectrophotometric investigation of the interaction of iodine with aromatic hydrocarbons. J Am Chem Soc 71:2703–2707
Kuntz ID Jr, Gasparro FP, Johnston MD Jr, Taylor RP (1968) Molecular interactions and the Benesi-Hildebrand equation J. Am Chem Soc 90:18
Davis KMC, Farmer MF (1967) Charge-transfer complexes. Part II Complex Formation between Halogenomethanes and Aromatic Amines J Chem SOC (B)
Ghatak S, Dey D, Sen S, Sen K (2013) Aromatic amino acids in high selectivity bismuth (III) recognition. Analyst. 138:2308–2314
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. J Lumin 116:35–42
Patil NR, Melavanki RM, Kapatkar SB, Chandrasekhar K, Ayachit NH, Umapathy S (2012) Solvent effect on the fluorescence quenching of biologically active carboxamide by aniline and carbon tetrachloride in different solvents using S–V plots. J Lumin 132:558–565
Thipperudrappa J, Biradar DS, Lagare MT, Hanagodimath SM, Inamdar SR, Kadadevaramath JS (2006) Fluorescence quenching of BPBD by aniline in benzene–acetonitrile mixtures. J Photochem Photobiol A Chem 177:89–93
Shivaram N. Patil, F.M. Sanningannavar, B.S. Navati, D. Nagaraja, N.R. Patil, R.M. Melavanki (2015) Can. J. Phys. Quenching mechanism of 5BDTC by aniline using Stern–Volmer plots. 93:1076–1081. https://doi.org/10.1139/cjp-2014-0613
Jun HY, Liu Y, Bo WJ, He XX, Sheng QS (2004) Study of interaction between monoammonium glycyrrhizinate and bovine serum albumin. J Pharm Biomed Anal 36:915–919
Seetharamappa J, Kamat BP (2004) Spectroscopic studies on the mode of interaction of an anticancer drug with bovine serum albumin. Chem Pharm Bull 52(9):1053–1057
Cynthia G. Zoski (2007) Handbook of electrochemistry, first ed. Elsevier Science, Amsterdam, Boston
Dai XX, Feng HL, Huang ZS, Wang MJ, Kuang DB, Meier H, Cao D (2015) Synthesis of phenothiazine-based di-anchoring dyes containing fluorene linker and their photovoltaic performance. J. Dyes. Pigm. 114:47–54
Rehm D, Weller A (1970) Kinetics of fluorescence quenching by electron and h-atom transfer. Isr J Chem 8:259–271
Lakowicz JR (2006) Principles of fluorescence spectroscopy third ed. Springer, New York
Shaikh SMT, Seetharamappa J, Kandagal PB, Manjunath DH, Ashoka H (2007) Spectroscopic investigations on the mechanism of interaction of bioactive dye with bovine serum albumin. J Dyes Pigm 74:665–671
Availability of Data and Material (Data Transparency)
All data recorded and analysed in this article are already included. Further for any clarification, data recorded or analysed during the current study are available from the corresponding author on reasonable request.
Code Availability (Software Application or Custom Code)
Not applicable for the present work.
Funding
The present work is not funded by any organization.
Author information
Authors and Affiliations
Contributions
All authors contributed to this work. Conceptualization: [Dr. Nirupama Jagadeeshwar M.], Synthesis of coumarin derivative [Dr. Netravati I. Khanapurmath], Formal analysis of the results and investigation [Dr. Nirupama Jagadeeshwar M. and Dr. Lakkanna S. Chougala], Writing-original draft preparation [Dr. Nirupama Jagadeeshwar M.]; review, suggestions and supervision [Prof. Manohar V. Kulkarni, Prof. Jagadish S. Kadadevarmath]. All authors read and approved the final manuscript.
Corresponding author
Ethics declarations
Conflict of Interest
This research work is not funded by any organization and has no potential conflict of interest.
Ethics Approval
This work is original and not submitted to any other journal in any form or language.
Consent to Participate
“Not applicable” to Nonlife science subjects.
Consent for Publication
“Not applicable” (This work does not include case study).
Additional information
Publisher’s Note
Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.
Rights and permissions
About this article
Cite this article
Jagadeeshwar, N.M., Khanapurmath, N.I., Chougala, L.S. et al. Role of Substituent Position in Coumarin Derivatives during their Interaction with TiO2 Nano Particles. J Fluoresc 31, 775–785 (2021). https://doi.org/10.1007/s10895-021-02706-3
Received:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1007/s10895-021-02706-3