Synthesis and structural studies on (<i>E</i>)-3-(2,6-difluorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one: a promising nonlinear optical material

Borges, Igor D.; Danielli, J. A. V.; Silva, V. E. G.; Sallum, Lóide O.; Queiroz, Jaqueline E.; Dias, Lucas D.; Iermak, Ievgeniia; Aquino, Gilberto L. B.; Camargo, Ademir J.; Valverde, Clodoaldo; Osório, Francisco A. P.; Baseia, B.; Napolitano, Hamilton B.

doi:10.1039/d0ra03634j

Cited by 17 publications

(11 citation statements)

References 55 publications

(62 reference statements)

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“…Band I of chalcones usually appears at 220–270 nm, while band II appears at 340–390 nm. To be more specific, trans-Chalcones yield band I and II near 230 and 300 nm, in which the intensity of band II is much stronger than band I [ 23 , 24 , 25 , 26 ]. These bands are generated from n → π * and π → π * electronic transitions [ 25 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Chalcone Derivatives as Novel Sunscreen Agent

et al. 2021

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Ultraviolet (UV) irradiation is a serious problem for skin health thus the interest in the research to develop sunscreen agent has been increasing. Chalcone is a promising compound to be developed as its chromophore absorbs in the UV region. Therefore, in the present work, we synthesized eight chalcone derivatives through Claisen–Schmidt condensation at room temperature. The evaluation of the optical properties of each chalcone derivatives in the UV region was conducted through spectroscopic and computational studies. The synthesized chalcones were obtained in good yields and they were active in the UV region. The results revealed that more methoxy substituents to chalcone leads toward red shift. All chalcone derivatives have high molar absorptivity value (21,000–56,000) demonstrating that they have the potential to be used as the sunscreen agent. The cytotoxicity assay showed that chalcone derivatives were demonstrating low toxicity toward normal human fibroblast cell, which is remarkable. Therefore, we concluded that the synthesized chalcones in this work were potential to be developed as novel sunscreen agents in real application.

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Section: Introductionmentioning

confidence: 99%

Synthesis and Evaluation of Chalcone Derivatives as Novel Sunscreen Agent

et al. 2021

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“…UV–vis spectrum of the ligand indicated sharp peak at 276 nm that corresponds to π–π* transitions within the phenyl and azomethine groups. [ 41 ] The construction of metal (II) and (III) complexes was also established by UV–vis study. Electronic spectra of the produced metal complexes were recorded in 1:1 (v/v) DMF:ethanol solution, in the wavelength range of 200–600 nm.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, characterization, antimicrobial, and docking study of novel 1‐(furanyl)‐3‐(pyrrolyl)propenone‐based ligand and its chelates of 3d‐transition metal ions

Zayed

Radwan

et al. 2021

Applied Organom Chemis

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The novel ligand (L) 1-(furanyl)-3-(pyrrolyl)propenone had been synthesized, and its novel chelates of some 3d series of transition metal ions had been prepared and characterized. The structural properties of the titled compounds were explored using elemental analyses, spectroscopic techniques (UV-visible, MS, and FT-IR), molar conductivity, and magnetic susceptibility measurements. The scanning electron microscope (SEM) showed that the ligand and its metal chelates exist in stick crystallized structures and sizes of their molecules can exist in nanoform. Thermal analyses techniques (TG and DTA) measured the investigated chelates during their thermal degradation to elucidate their structures. It was proved that ligand (L) acts as bibasic bidentate ligand coordinating to metal cations via its two oxygen atoms of carbonyl and epoxy groups. The optimization of the structural formula for the examined ligand had been performed by using Gaussian 09 program. The energy gaps were calculated using the DFT/B3LYP method. The ligand and its chelates had been fixed to have consistent bond lengths and bond angles that proved via quantum chemical factors. The ligand (L) and its transition metal chelates had been tested for their antibacterial activities. In vitro biological properties for ligand (L) and its transition metal complexes were carried out against Gram-positive bacteria (Bacillus subtilis and Staphylococcus aureus) and Gram-negative bacteria (Escherichia coli and Pseudomonas aeruginosa) by agar diffusion technique.The results showed that title compounds are biologically active than the parent ligand in their sticks crystalline and possible nanostructures and consequently large surface interactions. Molecular docking showed favorable interaction between ligand and crystal structures of 3t88 E. coli, 3ty7 S. aureus, 5h67 B. subtilis, and 5i39 P. aeruginosa. This docking study proved that nanosize of ligand helps it to interact efficiently with proteins of bacteria.

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“…In a series of recent papers, we have used an electrostatic embedding approach, which mimics the inhomogeneous crystal polarizing field, for polarizing molecules in different crystalline environments. [25][26][27][28][29][30][31][32][33][34][35][36] In addition, this approach also represents an efficient tool to estimate the refractive index and the third-order nonlinear optical susceptibility of chalcone derivative crystals. [37][38][39][40][41][42][43][44][45] This study proposes to combine the synthesis, molecular structure, and packaging of two new isostructural compounds, (E)-3-(4-bromobenzylidene)-2-(2-methoxyphenyl)-1-(phenylsulfonyl)-2,3-dihydroquinolin-4(1H)-one (BMP) and (E)-3-(4-chlorobenzylidene)-2-(2-methoxyphenyl)-1-(phenylsulfonyl)-2,3-dihydroquinolin-4 (1H)-one (CMP) with quantum chemical calculations using an electrostatic embedding approach, in which the surrounding molecules are represented by point charges, to better understand the impact of halogenated substituents on the NLO properties of the BMP and CMP crystals.…”

Section: Introductionmentioning

confidence: 99%

“…In a series of recent papers, we have used an electrostatic embedding approach, which mimics the inhomogeneous crystal polarizing field, for polarizing molecules in different crystalline environments. 25–36 In addition, this approach also represents an efficient tool to estimate the refractive index and the third-order nonlinear optical susceptibility of chalcone derivative crystals. 37–45…”

Section: Introductionmentioning

confidence: 99%

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Molecular modeling and nonlinear optical properties of new isostructural halogenated dihydroquinolinones

et al. 2022

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Synthesis and structural studies on (E)-3-(2,6-difluorophenyl)-1-(4-fluorophenyl)prop-2-en-1-one: a promising nonlinear optical material

Abstract: 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.

Cited by 17 publications

References 55 publications

Synthesis and Evaluation of Chalcone Derivatives as Novel Sunscreen Agent

Synthesis and Evaluation of Chalcone Derivatives as Novel Sunscreen Agent

Synthesis, characterization, antimicrobial, and docking study of novel 1‐(furanyl)‐3‐(pyrrolyl)propenone‐based ligand and its chelates of 3d‐transition metal ions

Molecular modeling and nonlinear optical properties of new isostructural halogenated dihydroquinolinones

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