DFT analysis and third-harmonic generation properties of one series of push–pull benzylidenemalononitrile derivatives

B. Sakki; S. Taboukhat; L. Messaadia; M. Guergouri; A. Bouraiou; R. Nasri; V. Figa; K. Bouchouit; B. Sahraoui

doi:10.1140/epjd/s10053-022-00424-4

2023 Impact factor 1.5

Atomic, Molecular, Optical and Plasma Physics

Eur. Phys. J. D (2022) 76: 101
https://doi.org/10.1140/epjd/s10053-022-00424-4

Regular Article – Molecular Physics and Chemical Physics

DFT analysis and third-harmonic generation properties of one series of push–pull benzylidenemalononitrile derivatives

B. Sakki¹^,2, S. Taboukhat³, L. Messaadia⁴, M. Guergouri⁵, A. Bouraiou¹^e, R. Nasri², V. Figa⁶, K. Bouchouit⁷^h and B. Sahraoui³^j

¹ Unité de Recherche de Chimie de 1’Environnement, et Moléculaire Structurale, CHEMS, Université Frères Mentouri, 25000, Constantine, Algeria
² Pollution and Water Treatment Laboratory, Department of Chemistry, Faculty of Exact Sciences, University of Constantine 1, Constantine, Algeria
³ Laboratory MOLTECH-Anjou, CNRS UMR 6200, University of Angers, 2 Bd Lavoisier, 49045, Angers Cedex, France
⁴ Laboratoire Énergétique Appliquée et Matériaux (LEAM), Université de Jijel, Ouled Aissa, Jijel, Algeria
⁵ Laboratoire de Chimie des Matériaux Constantine, Université des Frères Mentouri Constantine 1, 25000, Constantine, Algeria
⁶ Euro-Mediterranean Institute of Science and Technology (IEMEST), via Michele, Miraglia 20, 90100, Palermo, Italy
⁷ Laboratoire de Didactique des Sciences Physiques, Chimiques et Applications, Ecole Normale Supérieure de Constantine, Ville Universitaire, Constantine, Algeria

^e bouraiou.abdelmalek@yahoo.fr
^h karim.bouchouit@laposte.net
^j bouchta.sahraoui@univ-angers.fr

Received: 13 July 2021
Accepted: 22 May 2022
Published online: 9 June 2022

Abstract

Optical and nonlinear optical properties of benzylidenemalononitrile derivatives with different electron-donating groups’ substituents were studied. Four benzylidenemalononitrile derivatives [benzylidenemalononitrile (1), (4-chlorobenzylidene)malononitrile (2), (4-hydroxybenzylidene)malononitrile (3) and (4-(dimethylamino)benzylidene)malononitrile (4)] were functionalized, synthesized and analyzed using 1H NMR, FTIR, and UV–vis. A study of electrochemical properties was conducted using cyclic voltammetry. The third-harmonic generation technique was used to analyze and evaluate the susceptibility ( $χ_{THG}^{< 3 >}$ $\chi_{{{\text{THG}}}}^{ < 3 > }$ ) of cubic nonlinear optical properties on thin films at 1064 nm. THG measurements using the Maker fringe technique were used to analyze and evaluate the susceptibility $χ_{}^{< 3 >}$ $\chi_{{}}^{ < 3 > }$ parameter of thin films of PMMA with embedded molecules. The studied benzylidenemalononitrile substituted with a strong electron-donating group showed considerable nonlinear responses. Theoretical analysis was performed using DFT/B3LYP/6-311G++ (d, p) and Gaussian 09 program quantum chemical calculations. Third-order nonlinear optical response increases proportionally with the electron-donating character of the substituent groups.