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Three chlorinated theinyl chalcone derivatives, namely ( E )-1-(5-chlorothiophen-2-yl)-3-(4-(methylthio)phenyl)prop-2-en-1-one ( I ), ( E )-1-(5-chlorothiophen-2-yl)-3-(4-(dimethylamino)phenyl)prop-2-en-1-one ( II ) and ( E )-1-(5-chlorothiophen-2-yl)-3-(2,3-dihydrobenzofuran-5-yl)prop-2-en-1-one ( III ), were synthesized and their crystal structures were determined by single-crystal X-ray diffraction analysis. Compounds  I ,  II  and  III  crystallize in the monoclinic space groups  P  2 1 / c  (centrosymmetric),  P  2 1 / n  (centrosymmetric) and  Pc  (non-centrosymmetric), respectively. In all three compounds, the molecules are in a relatively planar conformation and adopt a  trans  configuration with respect to the C=C double bond. The crystal packings are stabilized by weak hydrogen-bonds, π · · · π, C–H · · · π and C–Cl · · · π interactions. The intermolecular contacts and lattice energies were further analyzed by Hirshfeld surface analysis. The third-order nonlinear optical properties of these chalcone derivatives were investigated using the single beam Z-scan technique with a 5 mW continuous wave diode laser operating at 635 nm, where compound  I  showed the highest potential for optical application with its exclusive nonlinear refractive index and nonlinear susceptibility.

zeitschrift für kristallographie - crystalline materials 

Third-order nonlinear optical properties of three chlorinated thienyl chalcones derivatives: synthesis, structural determination and Hirshfeld surface analysis