Substituent and solvent effects on the spectroscopic properties and dipole moments of hydroxyl benzaldehyde azo dye and related Schiff bases

Absorption and emission spectra of salicylaldehyde azo and related two Schiff bases with the same molecular skeletons and different functional groups have been studied in various solvents with different polarities. The solute's photo-physical behavior depends strongly on the solvent–solute inte...

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Bibliographic Details
Published in:Journal of molecular liquids 2013-04, Vol.180, p.225-234
Main Authors: Zakerhamidi, M.S., Nejati, K., Golghasemi Sorkhabi, Sh, Saati, M.
Format: Article
Language:English
Subjects:
Enol-imine
Excited state intramolecular proton transfer
Keto-enamine
Salicylaldehyde azo
Schiff base
Tautomerism
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Summary:Absorption and emission spectra of salicylaldehyde azo and related two Schiff bases with the same molecular skeletons and different functional groups have been studied in various solvents with different polarities. The solute's photo-physical behavior depends strongly on the solvent–solute interactions and solvent microenvironment as well as resonance structures of the salicylaldehyde azo and related Schiff bases. In order to understand the effects of intermolecular interactions on spectral behavior of these substances and to conceive nature and extent of solvent–solute interactions the spectral variations were analyzed by the linear solvation energy relationship concept. In addition, the variations of dye dipole moments, from ground to excited states, were investigated in solvent media by means of solvatochromic method. [Display omitted] ► 2-Hydroxy Schiff bases mainly interesting due to the existence of proton tautomerism ► We suggest excited state intramolecular proton transfer takes place in these matters. ► Existing some intermediate in transformation of enol to keto form.
ISSN:0167-7322
1873-3166
DOI:10.1016/j.molliq.2013.01.021