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

Kocak R., Yildiz D., BOZKAYA U., DAŞTAN A., BOZDEMİR Ö. A.

TETRAHEDRON LETTERS, vol.58, no.30, pp.2981-2985, 2017 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 58 Issue: 30
  • Publication Date: 2017
  • Doi Number: 10.1016/j.tetlet.2017.06.059
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.2981-2985
  • Hacettepe University Affiliated: Yes


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.