Solvatochromism, tautomerism and dichroism of some azoquinoline dyes in liquids and liquid crystals

Absorption and emission spectra of three hetarylazoquinoline compounds with different substituents were examined in liquids and liquid crystalline solvents for the first time. The spectral features of the hetarylazoquinoline dyes were explained according to azo/hydrazone tautomerism in conjunction with the solvatochromic characteristic of the preferred tautomer. The nature and extent of solute–solvent interactions were described using Kamlet–Taft and Katritzky multiparameter polarity scales. It was observed that solvatochromic azo/hydrazone tautomerism depend on multiple solute-solvent interactions, in particular on specific interactions and the solvent ability to transport the hydrogen atom through the media. In addition, it was concluded that anisotropic hosts prevent shift of the tautomeric equilibrium toward the hydrazone form.

Graphical abstractFigure optionsDownload full-size imageDownload as PowerPoint slideHighlights► Spectral data of three new synthesized azo dyes were studied. ► Anisotropic hosts prevent the formation of hydrazone tautomer. ► Solute–solvent interactions were described using multiparameter polarity scales.