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An Insight into Photophysical Investigation of (E)-2-Fluoro-N’-(1-(4-Nitrophenyl)Ethylidene)Benzohydrazide through Solvatochromism Approaches and Computational Studies

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Abstract

A fluoro-based Schiff base (E)-2-fluoro-N′-(1-(4-nitrophenyl)ethylidene)benzohydrazide (FNEB) has been synthesized from condensation of 2-fluorobenzohydrazide and 4′-nitroacetophenone catalyzed by glacial acetic acid with ethanol as the solvent. The dipole moment of FNEB in both the electronic states were found using different solvatochromic approaches such as Lippert-Mataga, Bakhshiev, Kawski-Chamma-Viallet, Reichardt and Bilot-Kawski. The experimental ground state dipole moment of FNEB was calculated using Guggenheim-Debye method and theoretical ground state dipole moment using Bilot-Kawski solvatochromic approach. The solvatochromic behavior of the Schiff base in different solvents was studied using absorption and emission spectra. Catalan and Kamlet-Abboud-Taft parameters were used from the multiple linear regression (MLR) analysis in order to study the solute-solvent interaction. The dipole moments were also calculated using Time Dependent-Density Functional Theory (TD-DFT). The chemical stability of FNEB was determined using computational and Cyclic Voltammetry by the use of obtained energy gap between the frontier orbitals. Using the frontier orbitals energy gap, global reactivity parameters were computed. Further, Light Harvesting efficiency was determined to comprehend the photovoltaic property of the Schiff base.

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Acknowledgements

The authors would like to thank Anthem Biosciences for FTIR and NMR analyses. The authors express heartfelt gratitude to Indian Institute of Science (IISc), Bengaluru, India for performing the computational analysis.

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This research did not receive any specific grant from funding agencies in the public, commercial, or not-for-profit sectors.

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Authors and Affiliations

  1. Department of Chemistry, Christ (Deemed to be University), Hosur Road, Bengaluru, Karnataka, 560029, India

    Ditto Abraham Thadathil, Shanu Varghese, K B Akshaya & Anitha Varghese

  2. Department of Chemistry, St Berchmans College (Autonomous), Changanassery, Kerala, 686101, India

    Renjith Thomas

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  1. Ditto Abraham Thadathil
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Correspondence to Anitha Varghese.

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Thadathil, D.A., Varghese, S., Akshaya, K.B. et al. An Insight into Photophysical Investigation of (E)-2-Fluoro-N’-(1-(4-Nitrophenyl)Ethylidene)Benzohydrazide through Solvatochromism Approaches and Computational Studies. J Fluoresc 29, 1013–1027 (2019). https://doi.org/10.1007/s10895-019-02415-y

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