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

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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 (\(\chi_{{{\text{THG}}}}^{ < 3 > }\)) 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 \(\chi_{{}}^{ < 3 > }\) 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.

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Data Availability Statement

This manuscript has no associated data, or the data will not be deposited. [Authors’ comment: All data are included in the article.]

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Authors and Affiliations

  1. Unité de Recherche de Chimie de 1’Environnement, et Moléculaire Structurale, CHEMS, Université Frères Mentouri, 25000, Constantine, Algeria

    B. Sakki & A. Bouraiou

  2. Pollution and Water Treatment Laboratory, Department of Chemistry, Faculty of Exact Sciences, University of Constantine 1, Constantine, Algeria

    B. Sakki & R. Nasri

  3. Laboratory MOLTECH-Anjou, CNRS UMR 6200, University of Angers, 2 Bd Lavoisier, 49045, Angers Cedex, France

    S. Taboukhat & B. Sahraoui

  4. Laboratoire Énergétique Appliquée et Matériaux (LEAM), Université de Jijel, Ouled Aissa, Jijel, Algeria

    L. Messaadia

  5. Laboratoire de Chimie des Matériaux Constantine, Université des Frères Mentouri Constantine 1, 25000, Constantine, Algeria

    M. Guergouri

  6. Euro-Mediterranean Institute of Science and Technology (IEMEST), via Michele, Miraglia 20, 90100, Palermo, Italy

    V. Figa

  7. Laboratoire de Didactique des Sciences Physiques, Chimiques et Applications, Ecole Normale Supérieure de Constantine, Ville Universitaire, Constantine, Algeria

    K. Bouchouit

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  1. B. Sakki
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Contributions

B.S was involved in synthesis, methodology, and results analysis. ST contributed to results analysis, investigation, resources. L.M was involved in theoretical analysis. M.G. and VF contributed to electrochemical study, investigation, and resources. A.B was involved in methodology, results analysis, writing—original draft, writing, and supervision. R.N contributed to spectroscopy and spectral analysis, methodology, results analysis. K.B was involved in methodology, software, validation, results analysis, investigation, resources, writing—original draft, and supervision. B.S contributed to investigation, writing, and supervision.

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Correspondence to A. Bouraiou, K. Bouchouit or B. Sahraoui.

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Sakki, B., Taboukhat, S., Messaadia, L. et al. DFT analysis and third-harmonic generation properties of one series of push–pull benzylidenemalononitrile derivatives. Eur. Phys. J. D 76, 101 (2022). https://doi.org/10.1140/epjd/s10053-022-00424-4

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