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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2020
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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, 1H, 13C and 19F 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 P21/c stabilized by the C–H/O and
C–H/F interactions and the p/p 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 (c(3)) were
calculated, and the results were compared with experimental data obtained from the literature. The c(3)-
value for the chalcone crystal is 369.294 10 22 m2 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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BORGES, I. D. et al. Synthesis and structural studies on ( E )-3-(2,6-difluorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one: a promising nonlinear optical material. RSC Advances, Cambridge, v. 10, p. 22542-22555, 2020. DOI: 10.1039/d0ra03634j. Disponível em: https://pubs.rsc.org/en/content/articlepdf/2020/ra/d0ra03634j. Acesso em: 17 abr. 2023.