Highly selective "turn-on" fluorescent and colorimetric sensing of fluoride ion using 2-(2-hydroxyphenyl)-2,3-dihydroquinolin-4(1H)-one based on excited-state proton transfer

Chem Asian J. 2014 Jan;9(1):146-52. doi: 10.1002/asia.201300816. Epub 2013 Oct 15.

Abstract

A simple, highly selective and sensitive colorimetric system for the detection of fluoride ion in an aqueous medium has been developed using 2-(2-hydroxyphenyl)-2,3-dihydroquinolin-4(1H)-one. This system allows selective "turn-on" fluorescence detection of fluoride ion, which is found to be dependent upon guest basicity. An excited-state proton transfer is proposed to be the signaling mechanism, which is rationalized by DFT and TD-DFT calculations. The present sensor can also be applied to detect fluoride levels in real water samples.

Keywords: chemosensors; excited-state proton transfer; fluorescence; fluoride ions; sensors.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Colorimetry
  • Fluorescence*
  • Fluorides / analysis*
  • Ions / analysis
  • Protons*
  • Quantum Theory
  • Quinolones / chemistry*
  • Water Pollutants, Chemical / analysis*

Substances

  • 2-(2-hydroxyphenyl)-2,3-dihydroquinolin-4(1H)-one
  • Ions
  • Protons
  • Quinolones
  • Water Pollutants, Chemical
  • Fluorides