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Experimental and Theoretical Spectroscopic Investigation on Coumarin Based Derivatives for Non-Linear Optoelectronics Application

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Abstract

The spectral properties of MBTC (4-((4-((Benzo[d]oxazol-2-ylthio)methyl)-1H-1,2,3-triazol-1-yl)methyl)-7-methoxy-2H-chromen-2-one), CBTC (4-((4(((5Chlorobenzo[d]oxazol-2-yl)thio)methyl)-1H-1,2,3-triazol-1-yl)methyl)-2H-benzo[h]chromen-2-one) and TBTC (4-((4-((Benzo[d]oxazol-2-ylthio)methyl)-1H-1,2,3-triazol-1-yl)methyl)6(tertbutyl)2Hchromen-2-one) were studied in series of solvents with different polarity at room temperature to explore their solvatochromic effect and dipole moment. Stokes shift revealed a bathochromic shift with varying solvent polarity for all molecules which implies π-π*transition. The ground state and excited state dipole moment of the molecules are calculated experimentally using salvatochromic methods like Lippert-Mataga, Bakhshiev, Kawaski-chamma-viallet, and Reichardt's microscopic solvent polarity functions and computationally by density functional theory (DFT) method. It is observed that the excited state dipole moment is higher than the ground state so synthesized molecules are more polar in the excited state than in the ground state. Using the DFT method HOMO and LUMO energy values were obtained and compared with values obtained by the cyclic voltammetry. Using the values of HOMO (highest occupied molecular orbital) and LUMO (lowest unoccupied molecular orbital) we have estimated energy gap, chemical hardness (ɳ), chemical softness (s), ionization potential (IP), electron affinity (EA), electronegativity (χ), electrophilicity (ω), and chemical potential (μ) of the molecules were estimated. The energy gap of MBTC, CBTC, and TBTC were found to be low, that is 3.861 eV, 3.822 eV, and 3.801 eV respectively, this indicates molecules are more reactive and it has the easiest π-π* transition. Further electrophilic and nucleophilic sites were figured out using molecular electrostatic potential (MESP) which is useful in photochemical reactions. Hence the quantum chemical calculation and spectroscopic properties of the molecules can give a better understanding of their use in an optoelectronic device.

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Acknowledgements

The authors are thankful to the authorities of USIC, KUD, for providing the instrumental facility for this research work.

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Authors and Affiliations

  1. Department of Studies in Physics, Karnatak University, Dharwad, 580003, Karnataka, India

    Bi Bi Ayisha Mulla, Malatesh S. Pujar & Ashok H. Sidarai

  2. Department of Chemistry, Karnatak University, Dharwad, 580003, Karnataka, India

    Aravind R. Nesaragi & Ravindra R. Kamble

  3. Vijayanagara Sri Krishnadevaraya University, Bellary, 583105, Karnataka, India

    Mussuvir Pasha K. M

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  1. Bi Bi Ayisha Mulla
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Contributions

All authors contributed to this study conceptions and design. Sample Preparation, data collection and analysis were Performed by Bi Bi Ayisha Mulla, Material synthesized by Dr. Aravind R Nesargi and Prof. Ravindra R Kamble. the first draft of the manuscript was written by Bi Bi Ayisha Mulla. Computational work has done by Dr. Mussuvir Pasha K M. Draft editing and overall review done by Dr. Malatesh S Pujar and Prof. Ashok H Sidarai. All authors read and approved the final manuscript.

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Correspondence to Ashok H. Sidarai.

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Mulla, B.B.A., Nesaragi, A.R., M, M.P.K. et al. Experimental and Theoretical Spectroscopic Investigation on Coumarin Based Derivatives for Non-Linear Optoelectronics Application. J Fluoresc 33, 161–175 (2023). https://doi.org/10.1007/s10895-022-03046-6

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