Solvent Effects and Metal Ion Recognition in Several Azulenyl-Vinyl-Oxazolones

Abstract

The spectral properties of several azulene-oxazolone derivatives containing a phenyloxazolone moiety linked to a substituted azulene ring via a C=C double bond were studied in different solvents of varying polarity. The solvatochromism and the ability of azulene-oxazolone derivatives to recognize heavy metal ions were investigated. In order to estimate the contribution of the non-specific and specific solute–solvent interactions, multiple linear regression analysis using Kamlet–Taft, Catalan and Laurence parameters was applied. These azulene derivatives demonstrate positive solvatochromism. The methyl and isopropyl substituents at the seven-membered azulene ring determine the highest red shifts of the absorption maxima of these azulenyl-vinyl-oxazolones. According to Catalan and Laurence models, the solvent polarizability is a more significant parameter in describing the solvatochromic properties of the azulene-oxazolone derivatives. The azulene-oxazolone compounds under study showed a good response to heavy metal cations (Cd2+, Hg2+, Cu2+ and Pb2+).

Keywords

• azulene-oxazolone derivatives
• electronic absorption spectra
• solvatochromism
• solvent polarity scales
• response to heavy metal cations