Dihydropyridazine-appended dibenzosuberenones as a new class of fluorophores: Application to fluoride sensing

Highly fluorescent, novel dihydropyridazine-appended dibenzosuberenone type dye molecules were obtained in a single step from simple compounds using Diels-Alder chemistry. This new fluorophore structure can be used for the construction of fluorescent chemosensors, as exemplified by selective and sensitive fluoride ion sensing. The -N-H protons in these structures are acidic enough to allow for fluoride-induced deprotonation, leading to a significant color change as well as a concomitant fluorescence quenching. These fluorophores possess large Stokes shifts, high quantum yields, and long fluorescence lifetimes; therefore, this study potentially paves the way for the construction of novel dye molecules for use in fluorescent dye applications. (C) 2017 Elsevier Ltd. All rights reserved.