Third order nonlinear optical properties of selected fluorinated chalcone derivatives

Anizaim, Ainizatul Husna; Arshad, Suhana; Zaini, Muhamad Fikri; Abdullah, Mundzir; Zainuri, Dian Alwani; Razak, Ibrahim Abdul

doi:10.1016/j.optmat.2019.109406

Cited by 24 publications

(9 citation statements)

References 51 publications

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“…Additionally, another halogenated vibrational frequency, which was C-F stretching, contributed a high intensity band and was found in both reported compounds. In CH-ClF, the C-F stretching mode was interpreted at 1154.5 cm −1 , meanwhile in CH-FF, it was observed at 1155 cm −1 ; both peaks were found to fall in an assumed range between 1155 to 1330 cm −1 in previous research [36]. The vibration wavenumber achieved in C-F stretching mode was higher than C-Cl due to the presence of the inductive effect between the C-F bond and fluorine, which triggered an increase in the force constant and higher wavenumber absorption [39].…”

Section: C-x Vibrationsmentioning

confidence: 70%

“…The results were interpreted by referring to previous research, which estimated about 1600 cm −1 for the conjugated C = C that was bonded to the carbonyl group [35]. As for the C-C stretching mode, the electronegativity effect between two carbon atoms caused small peak contributions to the spectrum, which were mostly insignificant [36]. In our studies, we found the vibrational frequencies of C-C of CH-ClF and CH-FF at the same wavenumber, 1055.5 cm −1 .…”

Section: = O Vibrationsmentioning

confidence: 81%

“…The new halogen chalcones, namely, (E)-3-(3-chlorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one (CH-ClF) and (E)-3-(3-fluorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one (CH-FF) contained a similar fluoro-substituent unit at the para-position of phenyl ring (R1) and different substituents at the meta-position of phenyl ring (R2). Both chalcones represented an acceptor-pi-acceptor (A-π-A) system [36,40], with the halogen substituents at both ends capped and carbonyls acting as electron-withdrawing groups. Both molecular structures crystallized in a monoclinic crystal system with P2 1 (CH-ClF) and P2 1 /c (CH-FF) space groups.…”

Section: Molecular and Crystal Structural Analysismentioning

confidence: 99%

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The Photovoltaic Performance of Sensitizers for Organic Solar Cells Containing Fluorinated Chalcones with Different Halogen Substituents

et al. 2021

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Two newly halogenated chalcones, derivatives of C15H10ClFO (CH-ClF) and C15H10F2O (CH-FF), were synthesized using the Claisen–Schmidt condensation method. Both compounds were crystallized using a slow evaporation method, forming a monoclinic crystal system with a space group of P21 and P21/c, respectively. The compounds were further analyzed using spectroscopic techniques such as Fourier Transform Infrared (FTIR), Nuclear Magnetic Resonance (NMR), and Ultraviolet–Visible (UV–vis) analyses. The single crystal X-ray diffraction method revealed the existence of C−H⋯O and C−H⋯F intermolecular interactions in CH-FF. Hirshfeld surface analysis was performed to confirm the existence of intermolecular interactions in the compounds. The molecular geometries obtained from the X-ray structure determination were further used to optimize the structures using density functional theory (DFT), with the B3LYP/6-311G++(d,p) basis set in the ground state. The TD-DFT/B3LYP method was used to obtain the electronic properties and the HOMO–LUMO energy gap. Both compounds exhibited A-π-A architecture with different halogen substituents in which the CH-FF, containing -fluoro substituents, possessed good electron injection ability due to its electronegative properties. This increased the flow of the charge transfer for the dye regeneration process and enhanced the efficiency of the dye-sensitized solar cell (DSSC).

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Section: C-x Vibrationsmentioning

confidence: 70%

Section: = O Vibrationsmentioning

confidence: 81%

Section: Molecular and Crystal Structural Analysismentioning

confidence: 99%

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The Photovoltaic Performance of Sensitizers for Organic Solar Cells Containing Fluorinated Chalcones with Different Halogen Substituents

et al. 2021

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“…However, the corresponding torsion angles for DFT reveal that the compounds are almost coplanar ( Table 1 ), -174.4 ( Fc1 ) and 169.0 ( Fc2 ). Stem from the fact that the optimization is performed in isolated conditions while the experimental XRD are easily affected by the crystal environment and hydrogen-bonding interactions, thus some angle difference might occur [ 27 ].…”

Section: Resultsmentioning

confidence: 99%

“…The designed Fc1 and Fc2 were prepared by Claisen Schmidt condensation method as outlined in Scheme 1 [ 27 ]. All solid and liquid reagents (Merck, Aldrich) handled in preparations were used without any further purification.…”

Section: Methodsmentioning

confidence: 99%

Comparative analyses of new donor-π-acceptor ferrocenyl-chalcones containing fluoro and methoxy-fluoro acceptor units as synthesized dyes for organic solar cell material

et al. 2020

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Two organometallic compounds known as ( E )-1-ferrocenyl-(3-fluorophenyl)prop-2-en-1-one ( Fc1 ) and ( E )-1-ferrocenyl-(3-fluoro-4-methoxyphenyl)prop-2-en-1-one ( Fc2 ) are designed and synthesized for application in dye-sensitized solar cell (DSSC) based on a donor-π-acceptor (D-π-A) architecture. By strategically introducing a methoxy group into the acceptor side of the compound, Fc2 which has adopted a D-π-A-AD structure are compared with the basic D-π-A structure of Fc1 . Both compounds were characterized by utilizing the IR, NMR and UV-Vis methods. Target compounds were further investigated by X-ray analysis and studied computationally using Density Functional Theory (DFT) and Time-Dependent DFT (TD-DFT) approaches to explore their potential performances in DSSCs. An additional methoxy group has been proven in enhancing intramolecular charge transfer (ICT) by improving the planarity of Fc2 backbone. This good electronic communication leads to higher HOMO energy level, larger dipole moment and better short-circuit current density (J sc ) values. Eventually, the presence of methoxy group in Fc2 has improved the conversion efficiency as in comparison to Fc1 under the same conditions.

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Crystal structure, third-order nonlinear optical property relationship, density functional theory, and in silico bio activity of organic non-centrosymmetric crystal (E)-1-(thiophen-2-yl)-3-(p-tolyl)prop-2-en-1-one

Sateesha,

Chinnam,

Ananthnag

et al. 2024

Struct Chem

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Third order nonlinear optical properties of selected fluorinated chalcone derivatives

Cited by 24 publications

References 51 publications

The Photovoltaic Performance of Sensitizers for Organic Solar Cells Containing Fluorinated Chalcones with Different Halogen Substituents

The Photovoltaic Performance of Sensitizers for Organic Solar Cells Containing Fluorinated Chalcones with Different Halogen Substituents

Comparative analyses of new donor-π-acceptor ferrocenyl-chalcones containing fluoro and methoxy-fluoro acceptor units as synthesized dyes for organic solar cell material

Crystal structure, third-order nonlinear optical property relationship, density functional theory, and in silico bio activity of organic non-centrosymmetric crystal (E)-1-(thiophen-2-yl)-3-(p-tolyl)prop-2-en-1-one

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