Third-order nonlinear optical properties of three chlorinated thienyl chalcones derivatives: synthesis, structural determination and Hirshfeld surface analysis
-
Weng Zhun Ng
,
Ching Kheng Quah
,
Yip-Foo Win
Abstract
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 21/c (centrosymmetric), P 21/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.
Acknowledgements
The authors thank Malaysian Government and Universiti Sains Malaysia for Research University Individual Grant (RUI) (1001/PFIZIK/8011080). Dr. P.S. Patil thanks Science and Engineering Research Board (SERB), Government of India, for Core Research Grant (EMR/2017/003632).
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Supplementary Material
The online version of this article offers supplementary material (https://doi.org/10.1515/zkri-2019-0039).
©2019 Walter de Gruyter GmbH, Berlin/Boston
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Articles in the same Issue
- Frontmatter
- Graphical Synopsis
- Inorganic Crystal Structures
- Stacking polytypes of mixed alkali gallides/indides A1–2(Ga/In)3 (A=K, Rb, Cs): synthesis, crystal chemistry and chemical bonding
- The effect of the withdrawal speed on properties of nickel oxide thin films
- Organic and Metalorganic Crystal Structures
- Structural studies on dihydropyrimidine derivatives as Mycobacterium tuberculosis coenzyme-A carboxylase inhibitors
- Crystal and molecular structures of boldenone and four boldenone steroid esters
- Third-order nonlinear optical properties of three chlorinated thienyl chalcones derivatives: synthesis, structural determination and Hirshfeld surface analysis
