A new chalcone structure of (E)-1-(4-Bromophenyl)-3-(napthalen-2-yl)prop-2-en-1-one: Synthesis, structural characterizations, quantum chemical investigations and biological evaluations

Thanigaimani, Kaliyaperumal; Arshad, Suhana; Khalib, Nuridayanti Che; Razak, Ibrahim Abdul; Arunagiri, C.; Subashini, A.; Sulaiman, Shaida Fariza; Hashim, Nik Mohd Hazrul Nik; Ooi, Kheng Leong

doi:10.1016/j.saa.2015.04.028

Cited by 40 publications

(14 citation statements)

References 59 publications

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“…The FT‐IR vibrations of C=O are located in the range of 1666–1651 cm −1 . In present study, DI‐MNTDO showed sharp absorption bands of C=Ovibrations in the domain of 1739–1657 cm −1 (DFT) and 1608 (Experimental).…”

Section: Resultssupporting

confidence: 54%

Crystal and Quantum Chemical Exploration of the Potent Monocarbonyl Curcuminoids to Unveil Their Structural and Intriguing Electronic Properties

et al. 2020

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The two isomeric trifluoromethane and nitro containing monocarbonylcurcuminoids: (1E,4E)‐2‐methyl‐1‐(4‐nitrophenyl)‐5‐(4 (trifluoromethyl)phenyl)penta‐1,4‐dien‐3‐one (DI‐MNTDO ) and (1E,4E)‐2‐methyl‐5‐(4‐nitrophenyl)‐1‐(4‐(trifluoromethyl)phenyl)penta‐1,4‐dien‐3‐one (MO‐MNTDO)have been prepared by two consecutive aldol condensation reactions. The chemical structures of the DI‐MNTDO and MO‐MNTDO have been determined using X‐ray crystallographic and spectrometric methods. The single crystal X‐Ray diffraction (SC‐XRD) data reveals that DI‐MNTDO contains two geometrically different molecules in the asymmetric unit, while, MO‐MNTDO contains one molecule in the asymmetric unit. Additionally, molecular geometric parameters, vibrational spectral analysis, as well as electronic properties of the above‐mentioned molecules have been studied utilizing DFT/B3LYP/6‐31G (d, p) approach. The UV‐Vis spectral analysis was performed utilizing the time‐dependent density functional theory (TD‐DFT) with the same level. The natural bond orbitals (NBOs) investigation has been carried out at the B3LYP/6‐311+G(d,p) approach to explain the intramolecular hyper conjugative interactions. A plausible concurrence is acquired between experimental and theoretical findings. The frontier molecular orbitals (FMOs) have been achieved by above‐mentioned level of theory. Subsequently, the global reactivity parameters are calculated using the energies of FMOs. The chemical potential (μ) order: [MO‐MNTDO (μ=‐5.0785 eV)] < [DI‐MNTDO (μ=‐4.9465 eV)]. The obtained findings in context of stability as well as reactivity indicate that DI‐MNTDO is more stable and less reactive as compared to MO‐MNTDO.

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Section: Resultssupporting

confidence: 54%

Crystal and Quantum Chemical Exploration of the Potent Monocarbonyl Curcuminoids to Unveil Their Structural and Intriguing Electronic Properties

et al. 2020

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“…Both compounds consisted of similar C-H contents, which led to similar wavenumber values. The C-H in-plane and C-H out-of-plane bending vibrations appeared at 1474-1167 cm −1 and 1023-715 cm −1 , respectively [33]. The C-H in-plane The sensitized cells were analyzed by a Keithley 2400 solar simulator in order to determine the output voltage and the current reading of the tested compounds, under irradiation of AM 1.5 simulated sunlight (CHF-XM-500 W) with an intensity of 100 ± 3 mW/cm 2 .…”

Section: C-h Vibrationsmentioning

confidence: 99%

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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“…However, this description must be questioned on two grounds; firstly, the HÁ Á ÁBr distance in question, 2.93 Å , is not significantly shorter than the sum, 2.94 Å , of the van der Waals radii (Rowland & Taylor, 1996), and secondly, it has been convincingly demonstrated that Br atoms bonded to C atoms are extremely poor acceptors even from good hydrogen-bond donors, such as O-H and N-H, and correspondingly worse from a weak donor, such as C-H (Brammer et al, 2001;Thallapally & Nangia, 2001). (Thanigaimani et al, 2015), is also an isomer of compound (II) but with the locations of the aryl and naphthyl units interchanged. Compound (V) also crystallizes in the space group P1, with reduced cell repeat vectors also similar to those of compounds (II) and (V), and with the interaxial angles all greater than 90 , although (V) is not isostructural with (II).…”

Section: Br34mentioning

confidence: 99%

Three closely related 1-(naphthalen-2-yl)prop-2-en-1-ones: pseudosymmetry, disorder and supramoleular assembly mediated by C—H...π and C—Br...π interactions

et al. 2017

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A new chalcone structure of (E)-1-(4-Bromophenyl)-3-(napthalen-2-yl)prop-2-en-1-one: Synthesis, structural characterizations, quantum chemical investigations and biological evaluations

Cited by 40 publications

References 59 publications

Crystal and Quantum Chemical Exploration of the Potent Monocarbonyl Curcuminoids to Unveil Their Structural and Intriguing Electronic Properties

Crystal and Quantum Chemical Exploration of the Potent Monocarbonyl Curcuminoids to Unveil Their Structural and Intriguing Electronic Properties

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

Three closely related 1-(naphthalen-2-yl)prop-2-en-1-ones: pseudosymmetry, disorder and supramoleular assembly mediated by C—H...π and C—Br...π interactions

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