Spectroscopic and quantum chemical study on a non-linear optical material 4-[(1E)-3-(5-chlorothiophen-2-yl)-3-oxoprop-1-en-1-yl] phenyl4-methylbenzene-1-sulfonate

Kumar, Rajesh and Karthick, T and Srivastava, Anubha and Gangopadhyay, Debraj and Parol, Vinay and Tandon, Poonam and Gupta, Archana and Kumar, Amit and Bhat, Subrahmanya K (2022) Spectroscopic and quantum chemical study on a non-linear optical material 4-[(1E)-3-(5-chlorothiophen-2-yl)-3-oxoprop-1-en-1-yl] phenyl4-methylbenzene-1-sulfonate. Journal of Molecular Structure, 1248. ISSN 0022-2860

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Abstract

Chalcone derivatives are known for their characteristic non-linear optical efficiency. In the present work, the relation between the molecular structure and non-linear optical properties of a synthesized chalcone derivative 4-[(1E)-3-(5-chlorothiophen-2-yl)-3-oxoprop-1-en-1-yl] phenyl4-methylbenzene-1- sulfonate (4TPMS) have been investigated by combined experimental and theoretical approaches. The title compound 4TPMS was characterized by spectroscopic techniques viz. Raman, FT-IR, UV-vis, and 1H NMR. Further, the experimental findings were validated by quantum chemical computations. The crys�talline geometry of 4TPMS was optimized to energy minima by employing density functional theory (DFT) with B3LYP/6-311++G(d,p) approximation level. Harmonic vibrational frequencies were calculated and the spectral assignments have been done by potential energy distribution (PED) analysis. Significant non-linear optical (NLO) responses of chalcone are mainly caused by charge delocalization between lone pair and antibonding molecular orbitals within the molecule. Hence, natural bond orbital (NBO) was per�formed to analyze the charge delocalization along with the stability of the molecule. The population anal�ysis based on Charges from Electrostatic Potentials using a Grid based method (CHELPG) was employed to understand the electrophilic/nucleophilic reaction sites. Moreover, the time-dependent density functional theory (TD-DFT) was employed to predict the ener�gies, absorption wavelengths (λmax) and oscillator strengths (f) of the electronic transitions. The TD-DFT calculation successfully reproduces the experimental UV-Vis spectrum of 4TPMS. The chemical shifts ob�served in 1H-NMR and the calculated GIAO shielding tensors also showed good agreement. A vibrational contribution to the NLO activity and the effect of charge delocalization on the NLO response were illus�trated by comparing the similar kind of chalcone derivativ

Item Type: Article
Uncontrolled Keywords: Chalcone derivative Non-linear optical response NMR chemical shifts Electronic transitions Vibrational contribution
Subjects: Engineering > MIT Manipal > Chemistry
Depositing User: MIT Library
Date Deposited: 03 Mar 2022 06:18
Last Modified: 03 Mar 2022 06:18
URI: http://eprints.manipal.edu/id/eprint/158338

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