Density Functional Studies of the Dipole Polarizabilities of Substituted Stilbene, Azoarene and Related Push-Pull Molecules

Hinchliffe, Alan; Nikolaidi, Beatrice; Machado, Humberto J. Soscún

doi:10.3390/i5050224

Cited by 34 publications

(19 citation statements)

References 10 publications

(8 reference statements)

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“…We found that the presence of an A and a D group does indeed give an enhancement to <α> over and above what would be expected on the basis of the pure additivity of contributions from A and D, and that a (much larger) enhancement could be produced by increasing the complexity/ length of the conjugated system. For the sake of completeness, we will reproduce key results from the short communication [13] in this paper.…”

Section: Introductionmentioning

confidence: 99%

“…The general idea is to find a level of theory that gives highly accurate values for the polarizability tensor, but naturally this aim has to be moderated with the cost of such calculations. For comparison with the early paper [13], we standardized on the following procedure. Geometries were optimized and characterized at the B3LYP/6-311G(2d,1p) level of theory and B3LYP/6-311++G(2d,1p) polarizabilities were calculated at this geometry.…”

Section: Routes To Polarizabilitiesmentioning

confidence: 99%

“…Finally, we should draw attention to a recent paper [13] where we reported a theoretical study of polarizabilities for the three benzene-ring molecules shown in Figure 2. Here, A and D are a selection of activating and deactivating groups such as NH 2 and NO 2 .…”

Section: Introductionmentioning

confidence: 99%

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Enhancement of molecular polarizabilities by the push-pull mechanism; a DFT study of substituted benzene, furan, thiophene and related molecules

et al. 2006

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Abstract:We report Density Functional Theory (DFT) studies of the dipole polarizabilities of benzene, furan and thiophene together with a number of substituted and related systems. All geometries were optimized (and characterized) at the B3LYP/6-311g(2d,1p) level of theory and polarizabilities then calculated with B3LYP/6-311++G(2d,1p). For the R-ring systems we find group polarizabilities in the order R = NO 2 ∼ OCH 3 ∼ CN ∼ CHO > NH 2 > OH > H = 0. For systems R-ring-R, <α> differs little from the additivity model, with small positive and negative increments. For systems D-ring-A (where D and A are deactivating and activating groups) we find a positive enhancement to <α> over and above the value expected on the basis of pure additivity for all pairs A and D studied. This enhancement can be increased greatly by extending the length of the conjugated chain to D-ring-CH=CH-ring-A and D-ring-N=N-ring-A systems. Empirical models of polarizability such as AM1 agree badly with the DFT calculations in an absolute sense but give excellent statistical correlation coefficients. Calculated <α>'s also agree well in a statistical sense with the molecular volumes calculated from molecular mechanics force fields Analysis of the results in terms of the π electrons alone is not satisfactory.

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Section: Introductionmentioning

confidence: 99%

Section: Routes To Polarizabilitiesmentioning

confidence: 99%

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Enhancement of molecular polarizabilities by the push-pull mechanism; a DFT study of substituted benzene, furan, thiophene and related molecules

et al. 2006

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“…The aim of this research is to investigate the effect of substituents of a group of eight azobenzene derivatives in trans and cis forms on structural and electronic properties by DFT method, which was widely and successfully used in studies concerning structural and electronic properties of azobenzene derivatives [6][7][8].…”

Section: Introductionmentioning

confidence: 99%

Density functional theory calculations on azobenzene derivatives: a comparative study of functional group effect

et al. 2015

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Density functional theory (DFT) calculations have been used to investigate the structural properties, dipole moments, polarizabilities, Gibbs energies, hardness, electronegativity, HOMO/LUMO energies, and chemical potentials of trans and cis configurations of eight para-substituted azobenzene derivatives. All properties have been obtained using the B3LYP functional and 6-31++G(d,p) basis set. The planar structures have been obtained for all optimized trans configurations. The energy difference between trans and cis configurations for considered derivatives was found to be between 64.2-73.1 kJ/mole. It has been obtained that the p-aminodiazo-benzene (ADAB) has the difference in the dipole moments between trans and cis forms higher than for trans and cis azobenzene.

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“…Polarizabilities were calculated at the same level of theory using the standard GAUSSIAN-09W keyword "Polar" [23]. This keyword means that the polarizabilities were obtained analytically rather than by numerical differentiation.…”

Section: Computational Proceduresmentioning

confidence: 99%

Theoretical Studies of Molecular Structures, Infrared Spectra, NBO and NLO Properties of Some Novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone Dyes

Eşme

Sağdınç

2016

Acta Phys. Pol. A

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The optimized geometrical structures, infrared spectra, molecular electrostatic potential, natural bond orbital and nonlinear optical properties of 5-phenylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridoine (1) and 5-(4-bromophenylazo)-6-hydroxy-4-phenyl-3-cyano-2-pyridoine (2) dyes with a detailed study on the azo-hydrazone tautomerism in the ground state have been investigated by density functional theory using B3LYP functional with 6-31G(d,p) basis set. Vibrational modes are assigned with the help of vibrational energy distribution analysis program. Highest occupied molecular orbital and lowest unoccupied molecular orbital energies of the (1) and (2) compounds with azo and hydrazone forms were calculated with the same method and basis set. Molecular parameters like global hardness (η), global softness (σ) and electronegativity (χ) were calculated with the results obtained from the highest occupied and lowest unoccupied molecular orbital energies. Nonlinear optical parameters (mean polarizability ( α ), the anisotropy of the polarizability ( ∆α ) and the mean first-order hyperpolarizability ( β )) of the title compounds were investigated theoretically. The atomic charges, electronic exchange interaction, and charge delocalization of the molecules have been studied by natural bond orbital analysis.

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Density Functional Studies of the Dipole Polarizabilities of Substituted Stilbene, Azoarene and Related Push-Pull Molecules

Cited by 34 publications

References 10 publications

Enhancement of molecular polarizabilities by the push-pull mechanism; a DFT study of substituted benzene, furan, thiophene and related molecules

Enhancement of molecular polarizabilities by the push-pull mechanism; a DFT study of substituted benzene, furan, thiophene and related molecules

Density functional theory calculations on azobenzene derivatives: a comparative study of functional group effect

Theoretical Studies of Molecular Structures, Infrared Spectra, NBO and NLO Properties of Some Novel 5-arylazo-6-hydroxy-4-phenyl-3-cyano-2-pyridone Dyes

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