Experimental and DFT insights into molecular structure and optical properties of new chalcones as promising photosensitizers towards solar cell applications

Makhlouf, M.M.; Radwan, A. M.; Ghazal, Basma

doi:10.1016/j.apsusc.2018.05.007

Cited by 104 publications

(28 citation statements)

References 54 publications

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“…Moreover, the decrease in the HOMO-LUMO energy gap indicates the ease of charge transfer interactions within the molecule, which may be responsible for the bioactivity of the molecules. [41][42][43] Linking biology data with DE HOMO-LUMO values herein this manuscript, DE HOMO-LUMO indicated that the trimethoxy derivative 4c, 2.05 eV, is the lowest while the chloro-methoxy derivative 4b, is the highest, 2.27 eV where the three investigated picolinamidines were ordered as 4c < 4a < 4b. Whereas, the median GI 50 's were ordered as 4c < 4b < 4a, therefore, the previous model is valid for compounds 4a and 4b, but not for 4c.…”

Section: Computational Studiesmentioning

confidence: 75%

“…[35][36][37][38] For example, cationic compound 4c data showed that C 4 40 respectively, and their energy explain the ultimate charge transfer. 41,42 Moreover, the HOMO-LUMO energy gap decrease shows the ease of charge transfer interactions, which may be responsible for the bioactivity of the molecules. 43 The 3D plots of frontier orbitals in the optimized geometry denote the red color for positive phase and the green one for the negative phase of wave function as shown in Fig.…”

Section: Computational Studiesmentioning

confidence: 99%

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Synthesis of new thienylpicolinamidine derivatives and possible mechanisms of antiproliferative activity

et al. 2020

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Section: Computational Studiesmentioning

confidence: 75%

Section: Computational Studiesmentioning

confidence: 99%

Synthesis of new thienylpicolinamidine derivatives and possible mechanisms of antiproliferative activity

et al. 2020

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“…HOMO and LUMO play noteworthy roles in ICT. [ 53–55 ] Within a molecule, the HOMO is confined on the electron‐rich sites that have the aptitude to donate electrons. In contrast, the LUMO is found on the electron‐deficient positions that display electron acceptability.…”

Section: Resultsmentioning

confidence: 99%

Synthesis, photophysical properties, and density functional theory studies of phenothiazine festooned vinylcyclohexenyl‐malononitrile

et al. 2020

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A novel phenothiazine derivative conjugated with vinylcyclohexenyl-malononitrile (PTZ-CDN) was synthesized through the Knoevenagel reaction of 10-octyl-10H-phenothiazine-3,7-dicarbaldehyde with 2-(3,5,5-trimethylcyclohex-2-en-1-ylidene)malononitrile and fully characterized. The UV-vis absorption spectra of PTZ-CDN in different solvents showed a λ max band at 497-531 nm with a high molar extinction coefficient attributed to intramolecular charge transfer (ICT) with the characteristics of a π-π* transition. Increasing the solvent polarity resulted in a bathochromic shift of λ max. The PTZ-CDN fluorescence emission spectra were more sensitive to increasing the solvent polarity than the absorption spectra; they displayed a blue shift of λ em by 85 nm. To understand the behaviour of the PTZ-CDN derivative, Stokes' shift (Δ νÞ with respect to the solvent polarity, Lippert-Mataga and linear solvation-energy relationship (LSER) models were applied in which the LSER showed better regression than the Lippert-Mataga plots (r 2 = 0.9627). Finally, the TD-density functional theory (DFT) electronic transition spectra in dioxane and dimethyl formamide (DMF) were calculated. The DFT data showed that λ max resulted from the support of the highest occupied molecular orbital to the lowest unoccupied molecular orbital transition with 74% and 99% in dioxane and DMF, respectively.

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“…HOMO and LUMO molecular orbitals play a significant role in understanding intramolecular charge transfer (ICT) . Within molecules, the HOMO is localized on electron‐rich moieties and demonstrates the capability to donate electrons.…”

Section: Resultsmentioning

confidence: 99%

Synthesis and photophysical studies on a new fluorescent phenothiazine‐based derivative

et al. 2020

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A new typical phenothiazine compound functionalized with thienyl-indandione derivative (PTZTID) was synthesized and characterized using spectral analysis (ultraviolet-visible (UV-vis) light, infrared (IR), 1 H nuclear magnetic resonance (NMR) and 13 C NMR tools). The UV-vis absorption spectra of the PTZTID solution in 1,4-dioxane showed two absorption bands attributed to localized aromatic π-π* transitions of conjugated aromatic moieties and intramolecular charge transfer with the characteristics of a π-π* transition. The fluorescence spectra exhibited a maximum emission wavelength at 580 nm. The effect of concentration on photophysical properties took the form of a minor hypsochromic shift, which was attributed to some extent to the occurrence of H-type aggregation of the PTZTID derivative. Binary solvent effects on the spectroscopic behaviour of PTZTID were measured at different H 2 O/1,4-dioxane ratios. Similarly, when increasing the water content, a hypsochromic shift was observed that resulted from H-type aggregation.Furthermore, geometry and electronic configurations of PTZTID were studied at density functional theory /B3LYP level and indicated that the compound had a nonplanar (butterfly structure). K E Y W O R D Scomputational studies, density functional theory, fluorescence, PTZTID

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Experimental and DFT insights into molecular structure and optical properties of new chalcones as promising photosensitizers towards solar cell applications

Cited by 104 publications

References 54 publications

Synthesis of new thienylpicolinamidine derivatives and possible mechanisms of antiproliferative activity

Synthesis of new thienylpicolinamidine derivatives and possible mechanisms of antiproliferative activity

Synthesis, photophysical properties, and density functional theory studies of phenothiazine festooned vinylcyclohexenyl‐malononitrile

Synthesis and photophysical studies on a new fluorescent phenothiazine‐based derivative

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