Second harmonic generation in pyrazoline derivatives of dibenzylideneacetones and chalcone: A combined experimental and theoretical approach

[Display omitted] •Second-order nonlinear response of three pyrazoline compounds was investigated.•The inclusion of pyrazole group increases the first-order hyperpolarizability.•Pyrazolines powdered crystals are up to 5 times more efficient than KDP for SHG.•Minor changes in molecular and crystallin...

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Bibliographic Details
Published in:	Journal of photochemistry and photobiology. A, Chemistry. Vol. 388; p. 112147
Main Authors:	de Araújo, Raiane Sodré, de Alcântara, Aline Moreira, Abegão, Luis M.G., de Souza, Yago Pereira, Brandão Silva, Antônio Carlos, Machado, Rogério, Joatan Rodrigues, José, Rodriguez Pliego, Josefredo, d'Errico, Francesco, Siqueira Valle, Marcelo, de Alencar, Márcio André Rodrigues Cavalcanti
Format:	Journal Article
Language:	English
Published:	Elsevier B.V 01-02-2020
Subjects:	Density functional theory First hyperpolarizability Hartree-Fock Pyrazoline Second harmonic generation Second harmonic generation Density functional theory Hartree-Fock First hyperpolarizability Pyrazoline
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Summary:	[Display omitted] •Second-order nonlinear response of three pyrazoline compounds was investigated.•The inclusion of pyrazole group increases the first-order hyperpolarizability.•Pyrazolines powdered crystals are up to 5 times more efficient than KDP for SHG.•Minor changes in molecular and crystalline structures influence strongly the SHG. In this work, we investigate theoretically and experimentally second harmonic generation (SHG) in three pyrazoline compounds, being two derivatives of dibenzylideneacetone (DBA) (C23H20N2 and C25H24N2O2) and one derivative of chalcone (C21H18N2). The compounds were synthesized after two steps employing a Claisen-Schmidt condensation followed by an addition-elimination reaction with phenylhydrazine. All compounds were characterized using NMR, FT-IR, UV-Vis, and XRD. We calculated the first-order hyperpolarizabilities of these molecules using program packages based on the time-dependent Hartree-Fock (TDHF) and density functional theory (DFT). SHG was characterized by Kurtz and Perry’s powder method. We observed that these organic crystals present SHG efficiencies up to 5 times larger than the KDP, and we associated these values to their molecular structure and crystalline arrangements. The values obtained experimentally and theoretically evidence that these compounds have good potential for application in electronic devices based on second-order nonlinear responses.
ISSN:	1010-6030 1873-2666
DOI:	10.1016/j.jphotochem.2019.112147