Chalcone-based molecules: Experimental and theoretical studies on the two-photon absorption and molecular first hyperpolarizability

• Published in: Spectrochimica acta. Part A, Molecular and biomolecular spectroscopy Vol. 227; p. 117772
• Main Authors: Abegão, Luis M.G., Santos, Francisco A., Fonseca, Ruben D., Barreiros, André L.B.S., Barreiros, Marizeth L., Alves, Péricles B., Costa, Emmanoel V., Souza, Gabriella B., Alencar, Márcio A.R.C., Mendonça, Cleber R., Kamada, Kenji, De Boni, Leonardo, Rodrigues, José Joatan
• Format: Journal Article
• Language: English
• Published: England Elsevier B.V 15.02.2020
• Subjects: Chalcones; First hyperpolarizability; Hyper-Rayleigh scattering; Nonlinear optics; Two-photon absorption; Z-scan; Two-photon absorption; Chalcones; Hyper-Rayleigh scattering; Z-scan; First hyperpolarizability; Nonlinear optics
• ISSN: 1386-1425; 1873-3557
• DOI: 10.1016/j.saa.2019.117772

Five chalcone-based molecules denominated by C-3 ((E)-1-(4-methoxyphenyl)-3-phenylprop-2-en-1-one), C-4 ((E)-1,3-bis(4-methoxyphenyl)prop-2-en-1-one), C-5 ((E)-1-(benzo[d][1,3]dioxol-5-yl)-3-(4-methoxyphenyl)prop-2-en-1-one), C-6 ((E)-3-(naphthalen-1-yl)-1-phenylprop-2-en-1-one) and C-7 ((E)-1-(4-methoxyphenyl)-3-(naphthalen-1-yl)prop-2-en-1-one) were synthesized by Claisen-Schmidt reaction in solution of NaOH in water/ethanol 2:1. The aldehydes used were benzaldehyde, anisaldehyde, and β-naphthaldehyde, while the used ketones were acetophenone, p-methoxyacetophenone, and 3,4-methylenedioxyacetophenone. Z-scan and hyper-Rayleigh scattering techniques were used to study the nonlinear optical properties of these compounds in dichloromethane medium. By using Z-scan technique with femtosecond pulses, two-photon absorption cross-sections (σTPA) were determined, while the first molecular electronic hyperpolarizabilities (βHRS) were evaluated by the hyper-Rayleigh scattering technique, with picosecond pulses. From the recorded two-photon absorption spectra, it was identified that compound C-7 presented the highest σTPA, regarding the HOMO-LUMO transition, with a value of 40 GM, while C-6 achieved the lowest value for the same transition with 13 GM. Concerning the values of the first molecular hyperpolarizability, compound C-4 presented the highest value, 38 × 10−30 cm4 statvolt−1, while C-3 presented the lowest βHRS value of about 16 × 10−30 cm4 statvolt−1. Time-dependent density functional theory calculations were used to simulate the one- and two-photon absorption spectra, as well to predict the theoretical value of βHRS in dichloromethane and vacuum medium. [Display omitted] •Synthesis and structural characterization of five chalcone-based molecules;•Experimental two-photon absorption spectra obtained with the Z-scan technique by using femtosecond pulses;•Experimental first molecular hyperpolarizability obtained with the HRS technique by using picosecond pulses;•Simulation of the one- and two-photon absorption spectra by using Gaussian 09;•Simulation of the first molecular hyperpolarizability by using Gaussian 09.