On the structural and spectroscopic properties of the thienyl chalcone derivative: 3-(5-Bromo-2-thienyl)-1-(4-nitrophenyl)-prop-2-en-1-one

Author(s)

de Toledo, T. A. ^[1] ; Bento, R. R. F. ^[1] ; da Costa, R. C. ^[2] ; Al-Maqtari, H. M. ^[3] ; Jamalis, J. ^[3] ; Pizani, P. S. ^[4]

Affiliation

^[1] Univ Fed Mato Grosso, Inst Fis, BR-78060900 Cuiaba, MT - Brazil

^[2] Univ Fed Campina Grande, Ctr Ciencias & Tecnol Agroalimentar, BR-58840000 Pombal, PB - Brazil

^[3] Univ Teknol Malaysia, Dept Chem, Fac Sci, Johor Baharu 81310, Johor - Malaysia

^[4] Univ Fed Sao Carlos, Dept Fis, BR-13565905 Sao Carlos, SP - Brazil

• Document type: Journal article
• Source: VIBRATIONAL SPECTROSCOPY; v. 99, p. 73-79, NOV 2018.
• Web of Science Citations: 0

Abstract

In this study, we investigate the structural and spectroscopic properties of the thienyl chalcone derivative 3-(5-Bromo-2-thienyl)-1-(4-nitrophenyl)-prop-2-en-1-one, C13H8BrNO3S, using nuclear magnetic resonance (H-1 and C-13 NMR), UV-vis and Fourier transform infrared spectroscopy (FTIR) and Raman spectroscopy at room conditions combined with density functional theory (DFT) and time-dependent DFT (TD-DFT) augmented with B3LYP/6-311G(d,p) and CAM-B3LYP/6.311G(d,p) basis sets, yielding valuable information on the molecular conformational preferences, vibrational assignments, optical properties and electronic transitions. The vibrational mode assignments of the most stable conformer of C13H8BrNO3S are discussed based on potential energy distribution (PED) analysis and establishing a comparison with a similar chemical structure. The temperature dependence on the Raman spectra of the C13H8BrNO3S shows a reversible phase transition in the range 443-443 K pointed out by the discontinuity in the d omega/dT of bands in the external and internal modes region. The UV-vis spectrum of the C13H8BrNO3S indicates a semiconductor behavior with an optical band gap of 2.6 eV, corresponding to the predicted value of 3.42 eV assigned as the electronic transition from the highest occupied molecular orbital (HOMO) to the lowest unoccupied molecular orbital (LUMO). TD-DFT calculations reveal that the electron donor and acceptor group substitution on the 1-phenyl-3-(thiophen-2-yl)prop-2-en-1-one affects its absorption and nonlinear activity. (AU)

• FAPESP's process: 13/07793-6 - CEPIV - Center for Teaching, Research and Innovation in Glass
• Grantee: Edgar Dutra Zanotto
• Support Opportunities: Research Grants - Research, Innovation and Dissemination Centers - RIDC