Publication detail

Study of the spectroscopic properties and first hyperpolarizabilities of disperse azo dyes derived from 2-amino-5-nitrothiazole

Year: 2008

Type of publication: článek v odborném periodiku

Name of source: Journal of Photochemistry and Photobiology A-Chemistry

Publisher name: Elsevier Science SA

Place: Lausanne

Page from-to: 23-33

Titles:

Language	Name	Abstract	Keywords
cze	Studium spektroscopických vlastností a prvních hyperpolarizabilit dispersních azo barviv odvozených od 2-amino-5-nitrothiazolu	Studium spektroscopických vlastností a prvních hyperpolarizabilit dispersních azo barviv odvozených od 2-amino-5-nitrothiazolu
eng	Study of the spectroscopic properties and first hyperpolarizabilities of disperse azo dyes derived from 2-amino-5-nitrothiazole	The solvatochromism and other spectroscopic and photophysical characteristics of four azo disperse dyes, derived from2-amino-5-nitrothiazole, were evaluated and interpreted with the aid of experimental data and quantum mechanical calculations. For the non-substituted compound two conformers, E and Z,were proposed for the isolated molecules, being the second one considerably less stable. The optimization of these structures in combination with a SCRF methodology (IEFPCM, simulating the molecules in a kontinuum dielectric with characteristics of methanol), suggests that the Z form is not stable in solution. This same behaviour is expected for the substituted compounds, which is corroborated by experimental data presented in previous investigations [A.E.H. Machado, L.M. Rodrigues, S. Gupta, A.M.F. Oliveira-Campos, A.M.S. Silva, J. Mol. Struct. 738 (2005) 239?245]. For the substituted compounds, two forms derived from E conformer (A and B) are possible. Quantum mechanical data suggest for the isolated molecules, that the low energy absorption band of the E conformers involve at least two close electronic states, having the low-lying excited state a 1(n,_) nature, and being the S2 state attributed to a 1(_,_) transition. The data also suggest a small energy gap between the absorption peaks of A and B, related to the easy conversion between these forms. For the structures optimized in combination with the applied SCRF methodology, an states inversion is observed for the substituted compounds, with a considerable diminish of the energy gap between A and B absorption peaks. The electronic spectra of these compounds are quite sensitive to changes in the solvent polarity. The positive solvatochromism is more evident in aprotic solvents, probably due to the polarization induced by the solute. These compounds do not fluoresce at 298K, but present a small but perceptible fluorescence at 77 K, which seems to be favoured by the nature of the group in the 2_-position of the pheny	azo dyes;2-amino-5-nitrothiazole

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