H-bond stabilization of a tautomeric coumarin-pyrazole-pyridine triad generates a PET driven, reversible and reusable fluorescent chemosensor for anion detection

Alkis M., Pekyilmaz D., Yalcin E., AYDINER B., DEDE Y., SEFEROĞLU Z.

DYES AND PIGMENTS, cilt.141, ss.493-500, 2017 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 141
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1016/j.dyepig.2017.03.011
  • Dergi Adı: DYES AND PIGMENTS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.493-500
  • Anahtar Kelimeler: Coumarin-pyrazolone-pyridine triad, Tautomerism, Anion detection, DFT calculations, PET, ESIPT, INTRAMOLECULAR PROTON-TRANSFER, FLUORIDE-ION, ON FLUORESCENT, AQUEOUS-MEDIA, STATE, DENSITY, SENSOR, RECOGNITION, RECEPTORS, LUMINESCENT
  • Gazi Üniversitesi Adresli: Evet

Özet

A coumarin based anion sensor utilizing pyrazole both as an electron donor and hydroxyl H-bond donor and pyridine as a tautomer stabilizer is reported. The chemosensor exhibits ON-OFF-ON states and is more sensitive to F- at the stoichiometric ratio of 1:1. The OFF state is due to PET and the role of pyrazole is two fold, both stabilization of the enol tautomer via H-bonding and hosting domain of electrons enabling PET. Moreover, the absorption and emission properties of chemosensor change drastically upon acidification. (C) 2017 Elsevier Ltd. All rights reserved.