3-Hydroxybenzo[ g]quinolones: dyes with red-shifted absorption and highly resolved dual emission

Abstract

New derivatives of 3-hydroxyquinolone (3HQ) with a fused benzene ring (3-hydroxybenzo[ g]quinolones) have been synthesized. They display a remarkable red shift of their absorption spectrum in comparison with other 3HQ analogs allowing their excitation by common He/Cd and Ar–ion lasers. As a result of their irreversible excited-state intramolecular proton transfer (ESIPT) reaction, they display a dual fluorescence in a series of solvents of varying polarities, starting from toluene to methanol. The dual emission of these dyes correlates well with solvent H-bond basicity, which is connected with the effect of this solvent property on the kinetics of the ESIPT reaction. In addition to their red-shifted absorption and fluorescence, these new derivatives show a larger separation of their two emission bands and a more appropriate range of their intensity ratio than the previously synthesized 3HQs. These properties allow an improved ratiometric evaluation of the local H-bond basicity of unknown environments, which will favor future applications of the new dyes in polymer and biological sciences.