Synthesis and structural studies on (E)-3-(2,6-difluorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one: a promising nonlinear optical material

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Borges, I. D. ^[1] ; Danielli, V, J. A. ; Silva, V. E. G. ^[2] ; Sallum, L. O. ^[2] ; de Queiroz, J. E. ^[2] ; Dias, L. D. ^[3] ; Iermak, I. ^[3] ; Aquino, G. L. B. ^[2] ; Camargo, A. J. ^[2] ; Valverde, C. ^{[2, 4]} ; Osorio, F. A. P. ^{[5, 6]} ; Baseia, B. ^{[7, 5]} ; Napolitano, H. B. ^{[2, 8]}

Afiliação do(s) autor(es)

^[1] Ctr Univ Anapolis, Lab Novas Mat, BR-75083515 Anapolis, Go - Brazil

^[2] Univ Estadual Goias, Grp Quim Teor & Estrutural Anapolis, BR-75001970 Anapolis, Go - Brazil

^[3] Univ Sao Paulo, Sao Carlos Inst Phys, BR-13566590 Sao Carlos, SP - Brazil

^[4] Univ Paulista, Lab Modelagem Mol Aplicada & Simulacao, BR-74845090 Goiania, Go - Brazil

^[5] Univ Fed Goias, Inst Fis, BR-74690900 Goiania, Go - Brazil

^[6] Pontificia Univ Catolica Goias, BR-13566590 Goiania, Go - Brazil

^[7] Univ Fed Paraiba, Dept Fis, BR-58051970 Joao Pessoa, Paraiba - Brazil

^[8] Danielli, J. A., V, Ctr Univ Anapolis, Lab Novas Mat, BR-75083515 Anapolis, Go - Brazil

• Tipo de documento: Artigo Científico
• Fonte: RSC ADVANCES; v. 10, n. 38, p. 22542-22555, JUN 14 2020.
• Citações Web of Science: 0

Resumo

A new fluorinated chalcone (E)-3-(2,6-difluorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one was synthesized in 90% yield and crystallized by a slow evaporation technique. Its full structural characterization and purity were determined by scanning electron microscopy, infrared spectroscopy, gas chromatography-mass spectrometry,H-1,C-13 and(19)F nuclear magnetic resonance, thermal gravimetric analysis (TGA), differential scanning calorimetry (DSC), Raman microspectroscopy, UV-Vis absorption spectroscopy, single crystal X-ray diffraction (XRD) and Hirshfeld surface (HS) analysis. The fluorinated chalcone crystallized in centrosymmetric space groupP2(1)/cstabilized by the C-HMIDLINE HORIZONTAL ELLIPSISO and C-HMIDLINE HORIZONTAL ELLIPSISF interactions and the pi MIDLINE HORIZONTAL ELLIPSIS pi contact. The crystalline environment was simulated through the supermolecule approach where a bulk with 378 000 atoms was built. The electric parameters were calculated at the DFT/CAM-B3LYP/6-311++G(d,p) level as function of the electric field frequency. The macroscopic parameters such as linear refractive index and third-order nonlinear susceptibility (chi((3))) were calculated, and the results were compared with experimental data obtained from the literature. The chi((3))-value for the chalcone crystal is 369.294 x 10(-22)m(2)V(-2), higher than those obtained from a few similar types of molecule, showing that the chalcone crystal can be considered as a nonlinear optical material. Also, molecular theoretical calculations such as infrared spectrum assignments, frontier molecular orbital analysis and MEP were implemented, revealing that the most positive region is around the hydrogen atoms of the aromatic rings, and electrophilic attack occurs on the carbonyl group. (AU)

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