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

Author(s):Show less -

Abegao, Luis M. G. ^{[1, 2]} ; Santos, Francisco A. ^[1] ; Fonseca, Ruben D. ^{[3, 4]} ; Barreiros, Andre L. B. S. ^[5] ; Barreiros, Marizeth L. ^[5] ; Alves, Pericles B. ^[5] ; Costa, Emmanoel V. ^[6] ; Souza, Gabriella B. ^[5] ; Alencar, Marcio A. R. C. ^[1] ; Mendonca, Cleber R. ^[3] ; Kamada, Kenji ^[7] ; De Boni, Leonardo ^[3] ; Rodrigues, Jr., Jose Joatan ^[1]

Affiliation

^[1] Univ Fed Sergipe, Dept Fis, BR-49100000 Sao Cristovao, SE - Brazil

^[2] Yale Univ, Sch Med, Dept Radiol & Biomed Imaging, 300 Cedar St, New Haven, CT 06520 - USA

^[3] Univ Sao Paulo, Inst Fis Sao Carlos, CP 369, BR-13560970 Sao Carlos, SP - Brazil

^[4] Univ Popular Cesar, Dept Fis, Valledupar 2000004, Cesar - Colombia

^[5] Univ Fed Sergipe, Dept Quim, BR-49100000 Sao Cristovao, SE - Brazil

^[6] Univ Fed Amazonas, Dept Quim, BR-69077000 Manaus, AM - Brazil

^[7] Natl Inst Adv Ind Sci & Technol, Ikeda, Osaka 5638577 - Japan

• Document type: Journal article
• Source: SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY; v. 227, FEB 15 2020.
• Web of Science Citations: 3

Abstract

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 beta-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 (sigma(TPA)) were determined, while the first molecular electronic hyperpolarizabilities (beta(HRS)) 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 sigma(TPA), 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 x 10(-30) cm(4) statvolt(-1), while C-3 presented the lowest beta(HRS) value of about 16 x 10(-30) cm(4) 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 beta(HRS) in dichloromethane and vacuum medium. (C) 2019 Elsevier B.V. All rights reserved. (AU)

• FAPESP's process: 16/20886-1 - Ultrafast nonlinear optical spectroscopy: Transient Absorption and optical Kerr Gate with polarization control
• Grantee: Leonardo de Boni
• Support Opportunities: Regular Research Grants
• FAPESP's process: 18/11283-7 - Nonlinear photonics: spectroscopy and advanced processing of materials
• Grantee: Cleber Renato Mendonça
• Support Opportunities: Research Projects - Thematic Grants