A coumarin-pyrazolone based fluorescent probe for selective colorimetric and fluorimetric fluoride detection: Synthesis, spectroscopic properties and DFT calculations


Babur B., SEFEROĞLU N. , SEFEROĞLU Z.

JOURNAL OF MOLECULAR STRUCTURE, vol.1161, pp.218-225, 2018 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 1161
  • Publication Date: 2018
  • Doi Number: 10.1016/j.molstruc.2018.01.076
  • Title of Journal : JOURNAL OF MOLECULAR STRUCTURE
  • Page Numbers: pp.218-225
  • Keywords: Coumarin, Pyrazolone, Fluorescence chemosensor, Selective fluoride detection, DFT, ANION RECOGNITION, PROTON-TRANSFER, NAKED-EYE, RECEPTORS, CHEMOSENSOR, SENSORS, DENSITY, WATER, CO2+, PET

Abstract

A novel coumarin based fluorescence anion chemosensor (P-1) bearing pyrazolone as a receptoric part was synthesized and characterized by using FT-IR, H-1/C-13 NMR and HRMS for the purpose of recognition of anions in DMSO. P-1 has four tautomeric structures and the most stable tautomeric form of P-1 was determined experimentally and theoretically. The chemosensor P-1 consists two receptoric parts as free amide N-H and enamine N-H which is stabilized intramolecular H-bonding with coumarin carbonyl oxygen. P-1 interacts selectively with fluoride anion via amide N-H. The selectivity and sensitivity of probe to various anions were determined with spectrophotometric and H-1 NMR titration techniques as experimentally and all results were also explained by theoretical calculations. (C) 2018 Elsevier B.V. All rights reserved.