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

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 chromatog...

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Autores principales: Borges, I. D., Danielli, J. A. V., Silva, V. E. G., Sallum, L. O., Queiroz, J. E., Dias, L. D., Iermak, I., Aquino, G. L. B., Camargo, A. J., Valverde, C., Osório, F. A. P., Baseia, B., Napolitano, H. B.
Formato: Online Artículo Texto
Lenguaje:English
Publicado: The Royal Society of Chemistry 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9054580/
https://www.ncbi.nlm.nih.gov/pubmed/35514582
http://dx.doi.org/10.1039/d0ra03634j
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author Borges, I. D.
Danielli, J. A. V.
Silva, V. E. G.
Sallum, L. O.
Queiroz, J. E.
Dias, L. D.
Iermak, I.
Aquino, G. L. B.
Camargo, A. J.
Valverde, C.
Osório, F. A. P.
Baseia, B.
Napolitano, H. B.
author_facet Borges, I. D.
Danielli, J. A. V.
Silva, V. E. G.
Sallum, L. O.
Queiroz, J. E.
Dias, L. D.
Iermak, I.
Aquino, G. L. B.
Camargo, A. J.
Valverde, C.
Osório, F. A. P.
Baseia, B.
Napolitano, H. B.
author_sort Borges, I. D.
collection PubMed
description 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, (1)H, (13)C 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 group P2(1)/c stabilized by the C–H⋯O and C–H⋯F interactions and the π⋯π 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 (χ((3))) were calculated, and the results were compared with experimental data obtained from the literature. The χ((3))-value for the chalcone crystal is 369.294 × 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.
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spelling pubmed-90545802022-05-04 Synthesis and structural studies on (E)-3-(2,6-difluorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one: a promising nonlinear optical material Borges, I. D. Danielli, J. A. V. Silva, V. E. G. Sallum, L. O. Queiroz, J. E. Dias, L. D. Iermak, I. Aquino, G. L. B. Camargo, A. J. Valverde, C. Osório, F. A. P. Baseia, B. Napolitano, H. B. RSC Adv Chemistry 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, (1)H, (13)C 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 group P2(1)/c stabilized by the C–H⋯O and C–H⋯F interactions and the π⋯π 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 (χ((3))) were calculated, and the results were compared with experimental data obtained from the literature. The χ((3))-value for the chalcone crystal is 369.294 × 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. The Royal Society of Chemistry 2020-06-12 /pmc/articles/PMC9054580/ /pubmed/35514582 http://dx.doi.org/10.1039/d0ra03634j Text en This journal is © The Royal Society of Chemistry https://creativecommons.org/licenses/by-nc/3.0/
spellingShingle Chemistry
Borges, I. D.
Danielli, J. A. V.
Silva, V. E. G.
Sallum, L. O.
Queiroz, J. E.
Dias, L. D.
Iermak, I.
Aquino, G. L. B.
Camargo, A. J.
Valverde, C.
Osório, F. A. P.
Baseia, B.
Napolitano, H. B.
Synthesis and structural studies on (E)-3-(2,6-difluorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one: a promising nonlinear optical material
title Synthesis and structural studies on (E)-3-(2,6-difluorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one: a promising nonlinear optical material
title_full Synthesis and structural studies on (E)-3-(2,6-difluorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one: a promising nonlinear optical material
title_fullStr Synthesis and structural studies on (E)-3-(2,6-difluorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one: a promising nonlinear optical material
title_full_unstemmed Synthesis and structural studies on (E)-3-(2,6-difluorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one: a promising nonlinear optical material
title_short Synthesis and structural studies on (E)-3-(2,6-difluorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one: a promising nonlinear optical material
title_sort synthesis and structural studies on (e)-3-(2,6-difluorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one: a promising nonlinear optical material
topic Chemistry
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC9054580/
https://www.ncbi.nlm.nih.gov/pubmed/35514582
http://dx.doi.org/10.1039/d0ra03634j
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