Test-strip-based fluorometric detection of fluoride in aqueous media with a BODIPY-linked hydrogen-bonding receptor

Angew Chem Int Ed Engl. 2014 Feb 17;53(8):2225-9. doi: 10.1002/anie.201307848. Epub 2014 Jan 23.

Abstract

The measurement of biologically relevant anions, such as fluoride, is an important task in analytical chemistry, in particular, for dental health and osteoporosis. Although a large number of fluoride probes are known, the applicability under relevant conditions is limited to a few examples. To improve this situation, BODIPY-amidothiourea dyes with varying hydrogen-bond donating strengths were developed, the most H-acidic of which (1 c) could detect F(-) from an inorganic source (NaF) in 50 % aqueous solution (DMSO/water 1:1, v/v) with 0.01 ppm sensitivity through selective fluorescence quenching by a photoinduced electron-transfer (PET) process. Use of the probe and a reference dye with a test-strip assay and a portable and rapidly recording lateral-flow fluorescence reader made determination of F(-) in neat aqueous solutions, such as spiked water samples and toothpaste extracts, possible in a self-referenced manner, achieving a detection limit of 0.2 ppm.

Keywords: amidothiourea; fluorescent probes; fluoride; hydrogen bonds; photoinduced electron transfer.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boron Compounds / chemistry*
  • Chemistry Techniques, Analytical / instrumentation*
  • Fluorescent Dyes / chemistry
  • Fluorides / analysis*
  • Fluorometry*
  • Hydrogen Bonding
  • Thiourea / chemistry
  • Water / chemistry

Substances

  • 4,4-difluoro-4-bora-3a,4a-diaza-s-indacene
  • Boron Compounds
  • Fluorescent Dyes
  • Water
  • Thiourea
  • Fluorides