Quadratic hyperpolarizabilities of nitro-substituted pseudo-linear dye molecules with ethylenic and azo bridges

Shuto, Y.

doi:10.1002/(sici)1097-461x(1996)58:4<407::aid-qua10>3.0.co;2-z

Cited by 9 publications

(5 citation statements)

References 57 publications

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“…The first reason is the difference between -NH 2 and -NEt 2 . Actually, Shuto calculated a difference between 4-NH 2 -4‘-NO 2 -azobenzene and 4-NEt 2 -4‘-NO 2 -azobenzene of 0.38 eV with a semiempirical method, which almost corresponds to our difference of 0.48 eV. Another possibility is that we used the molecular geometry of thiazole for the thiazole unit and the same geometry for the azo group as in azobenzene.…”

Section: Resultsmentioning

confidence: 54%

“…Previous theoretical investigations of the electronic structure of azobenzene dyes have been limited to semiempirical calculations apart from a few exceptions. Semiempirical calculations of their electronic excitation energies − and of its optical properties 27-31 have been carried out. Furthermore, density functional theory (DFT) and second-order Møller−Plesset (MP2) calculations have been used to calculate the structure and vibrational frequencies of azobenzene , and their excited states have been studied by a configuration interaction (CI) method, but in this latter study the basis set was limited to the STO-3G basis set.…”

Section: Introductionmentioning

confidence: 99%

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Ab Initio Calculation of the Electronic Spectrum of Azobenzene Dyes and Its Impact on the Design of Optical Data Storage Materials

et al. 2000

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Electronic excitation energies of 16 azobenzene dyes have been calculated by ab initio methods within the second-order polarization propagator approximation (SOPPA). Good agreement with expriment is found for the lowest singlet and triplet states for both the trans-and cis-azobenzene molecules. The differences are in the range of (0.3 eV, with the exception of the lowest n f π * transition in trans-azobenzene, where a deviation of -0.64 eV is found. The lowest π f π * transition in trans-azobenzene, on the other hand, is particularly well reprensented with a deviation of only -0.15 eV. Furthermore, the experimental singlet π f π * transitions are reproduced for a set of azobenzene dyes with different electron donor and acceptor groups and the correct shifts in excitation energy are obtained for the different substituents. It has also been demonstrated that ab initio methods can be used to determine suitable candidates for azo components used in materials for data storage.

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Section: Resultsmentioning

confidence: 54%

Section: Introductionmentioning

confidence: 99%

Ab Initio Calculation of the Electronic Spectrum of Azobenzene Dyes and Its Impact on the Design of Optical Data Storage Materials

et al. 2000

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“…The different bonds included into the models are either within the azobenzene skeleton (no. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] or between the skeleton and the substituents (no. [16][17][18][19][20][21][22][23][24][25].…”

Section: Resultsmentioning

confidence: 99%

“…1 Furthermore, azobenzenes have also been considered as active components in carbonbased photonic devices for information storage. [2][3][4][5][6] Consequently, the electronic structure of azo dyes has been studied extensively both with semi-empirical [7][8][9][10][11][12][13][14][15][16][17][18] and ab initio methods, [19][20][21][22][23][24][25][26] and the success of semi-empirical methods to describe the pp* excitation energy is noted.…”

Section: Introductionmentioning

confidence: 99%

Quantitative prediction of the absorption maxima of azobenzene dyes from bond lengths and critical points in the electron density

Buttingsrud

Alsberg

Åstrand

2007

Phys. Chem. Chem. Phys.

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The relationship between the molecular electronic structure and the position of the absorption maxima in 191 azobenzene dyes has been studied by quantitative structure-property relations. A strong linearity is observed between the nitrogen-nitrogen bond length and the absorption wavelength with a squared correlation coefficient of 0.90. Bond lengths and properties of the critical points located on the electron density distribution are used to build partial least squares regression models for quantitative prediction of absorption wavelengths. Fifty of the azobenzene dyes were used as an external test set to evaluate the overall performance of the models. The simplest model where only the nitrogen-nitrogen bond length is used as a descriptor gives a root mean square error of prediction of 12.6 nm. When the value, laplacian and ellipticity of the electron density in all comparable bond critical points are used, the error of prediction is reduced to 5.4 nm. However, this model is less general and robust to prediction of novel molecular structures. It is demonstrated that the nitrogen-nitrogen bond in the azobenzene compounds relates to the colour of the dyes and in particular the nitrogen-nitrogen bond length plays a central role.

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“…On the basis of ab initio calculations, the azo linker has been reported to increase compound polarizability by acting as an auxiliary electron acceptor to the benzothiazole ring. 32 Alternatively, displacement affinity could be raised by increasing the surface area of the π-bridge ( 48B and 49B ). Both of these π-bridge modifications promote polarizability in the context of neutral molecules.…”

Section: Discussionmentioning

confidence: 99%

QSAR studies for prediction of cross-β sheet aggregate binding affinity and selectivity

Cisek

Kuret

2012

Bioorganic & Medicinal Chemistry

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Protein aggregates that accumulate in neurodegenerative diseases are important targets of radiotracer discovery efforts. Although multiple scaffold classes have been reported to bind cross-beta sheet structure, their mechanism of binding and their ability to interact selectively with aggregates of varying protein composition are not well understood. Here we take a ligand-based quantitative structure activity relationship approach to identify descriptors of binding affinity and selectivity for a series of fifty closely related benzothiazole derivatives reported to displace Thioflavin T fluorescent probe from synthetic aggregates composed of beta-amyloid peptide and insulin. Using a two-step workflow involving both partial least squares and multiple linear regression methods, compound polarizability and hydrophobicity were identified as tunable mediators of binding selectivity. The correlations also revealed how polarizability could be modulated in neutral compounds having push-pull character. These data suggest that the relative affinity of small molecules for binding sites exposed on aggregate surfaces can be modulated by simple chemical design considerations that are compatible with multiple scaffolds.

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Quadratic hyperpolarizabilities of nitro-substituted pseudo-linear dye molecules with ethylenic and azo bridges

Cited by 9 publications

References 57 publications

Ab Initio Calculation of the Electronic Spectrum of Azobenzene Dyes and Its Impact on the Design of Optical Data Storage Materials

Ab Initio Calculation of the Electronic Spectrum of Azobenzene Dyes and Its Impact on the Design of Optical Data Storage Materials

Quantitative prediction of the absorption maxima of azobenzene dyes from bond lengths and critical points in the electron density

QSAR studies for prediction of cross-β sheet aggregate binding affinity and selectivity

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