Study on the prediction of visible absorption maxima of azobenzene compounds

被引：327

作者：

Liu J.-N. ^{[1
]}

Chen Z.-R. ^{[1
]}

Yuan S.-F. ^{[1
]}

机构：

[1] School of Materials Science and Chemical Engineering, Zhejiang University

来源：

Journal of Zhejiang University-SCIENCE B | 2005年 / 6卷 / 6期

关键词：

Azobenzene compound; Nature bond orbital (NBO); Visible absorption maxima;

D O I：

10.1631/jzus.2005.B0584

中图分类号：

学科分类号：

摘要：

The geometries of azobenzene compounds are optimized with B3LYP/6-311G* method, and analyzed with nature bond orbital, then their visible absorption maxima are calculated with TD-DFT method and ZINDO/S method respectively. The results agree well with the observed values. It was found that for the calculation of visible absorption using ZINDO/S method could rapidly yield better results by adjusting OWFπ-π (the relationship between π-π overlap weighting factor) value than by the TD-DFT method. The method of regression showing the linear relationship between OWFπ-π and BLN-N (nitrogen-nitrogen bond lengths) as OWFπ-π=-8.1537+6.5638BLN-N, can be explained in terms of quantum theory, and also be used for prediction of visible absorption maxima of other azobenzne dyes in the same series. This study on molecules' orbital geometry indicates that their visible absorption maxima correspond to the electron transition from HOMO (the highest occupied molecular orbital) to LUMO (the lowest unoccupied molecular orbital).

引用

页码：584 / 589

页数：5

共 15 条

[1]

Alan E.R., Larry A.C., Frank W., Intermolecular interaction from a natural bond orbital donor-acceptor viewpoint, Chem. Rev., 88, 6, pp. 899-926, (1988)

[2]

Carlo A., Gustaro E.S., Vincenzo B., Accurate excitation energies from time-dependent density functional theory: Assessing the PBEO model, J. Chem. Phys., 111, 7, pp. 2889-2899, (1999)

[3]

Carpenter J.E., Weinhold F., Analysis of the geometry of the hydroxymethyl radical by the different hybrids for different spins natural bond orbital procedure, J. of Mol. Struct. (Theochem), 169, pp. 41-62, (1988)

[4]

Cheng L.B., Chen X., Gao K.Y., Hu J.Z., Griffiths J., Colour and constitution of azo dyes derived from 2-thioalkyl-4,6-diaminopyrimidines and 3-cyano-1,4-dimethyl-6-hydroxy-2-pyridone as coupling components, Dyes Pigm., 7, pp. 373-388, (1986)

[5]

Cheng L.B., Chen X., Hou Y.F., Griffiths J., An approach to the prediction of absorption bandwidths of dyes using the PPP-MO procedure, Dyes Pigm., 10, pp. 123-140, (1989)

[6]

Griffiths J., Practical aspects of colour prediction of organic dye molecules, Dyes Pigm., 3, pp. 211-233, (1982)

[7]

Kogo Y., Colour and constitution of thiophene and thiazole azo dyes, Dyes Pigm., 6, pp. 31-38, (1985)

[8]

Liao Y., Su Z.M., Chen Y.G., Kan Y.H., TD-DFT study on electronic spectrum property for bis(8-hydroxyquinoline) beryllium and its derivatives, Chem. J. Chinese Univers., 24, 3, pp. 477-480, (2003)

[9]

Lu R.W., Zhang Y.L., Gao K.Y., The spectrum and staining properties of some azo benzene disperse dyes, Dyestuff Industry, 30, 3, pp. 1-5, (1993)

[10]

Machado A.E.H., Miranda J.A., Guilardi S., Nicodem D.E., Severino D., Photophysics and spectroscopic properties of 3-benzoxazol-2-yl-chromen-2-one, Spectrochim. Ada., Part A, 59, pp. 345-355, (2003)

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