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Int. J. Mol. Sci. 2011, 12(12), 8895-8912; doi:10.3390/ijms12128895

Spectroscopic Study of Solvent Effects on the Electronic Absorption Spectra of Flavone and 7-Hydroxyflavone in Neat and Binary Solvent Mixtures

1
Physical Chemistry Laboratory, Faculty of Chemistry, Biochemistry and Pharmacy, San Luis National University, 5700 San Luis, Argentina
2
Multidisciplinary Institute of Biological Investigations (IMIBIO-SL) CONICET, 5700 San Luis, Argentina
3
INIFTA, Chemistry Department, Faculty of Exact Sciences, La Plata National University, 1900 Buenos Aires, Argentina
*
Author to whom correspondence should be addressed.
Received: 6 September 2011 / Revised: 5 November 2011 / Accepted: 14 November 2011 / Published: 5 December 2011
(This article belongs to the Special Issue Advances in Molecular Electronic Structure Calculations)
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Abstract

The solvatochromic characteristics of flavone and 7-hydroxyflavone were investigated in neat and binary solvent mixtures. The spectral shifts of these solutes were correlated with the Kamlet and Taft parameters (α, β and π*) using linear solvation energy relationships. The multiparametric analysis indicates that both specific hydrogen bond donor ability and non-specific dipolar interactions of the solvents play an important role in absorption maxima of flavone in pure solvents. The hydrogen bond acceptor ability of the solvent was the main parameter affecting the absorption maxima of 7-hydroxyflavone. The simulated absorption spectra using a TD-DFT method were in good agreement with the experimental ones for both flavones. Index of preferential solvation was calculated as a function of solvent composition. Preferential solvation by ethanol was detected in cyclohexane-ethanol and acetonitrile-ethanol mixtures for flavone and in acetonitrile-ethanol mixtures for 7-hydroxyflavone. These results indicate that intermolecular hydrogen bonds between solute and solvent are responsible for the non-linear variation of the solvatochromic shifts on the mole fraction of ethanol in the analyzed binary mixtures.
Keywords: flavones; solvatochromism; LSER; preferential solvation; TD-DFT calculations flavones; solvatochromism; LSER; preferential solvation; TD-DFT calculations
This is an open access article distributed under the Creative Commons Attribution License (CC BY 3.0).

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Sancho, M.I.; Almandoz, M.C.; Blanco, S.E.; Castro, E.A. Spectroscopic Study of Solvent Effects on the Electronic Absorption Spectra of Flavone and 7-Hydroxyflavone in Neat and Binary Solvent Mixtures. Int. J. Mol. Sci. 2011, 12, 8895-8912.

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