Fluorene-based boronic acids as fluorescent chemosensor for monosaccharides at physiological pH

Luminescence. 2015 Aug;30(5):549-55. doi: 10.1002/bio.2776. Epub 2014 Sep 29.

Abstract

Two fluorene-based boronic acids, 9,9-dimethyl-9H-fluoren-2-yl-2-boronic acid (1) and 9,9-dimethyl-9H-fluoren-2,7-diyl-2,7-diboronic acid (2), were synthesized and their sensing abilities for detection of D-monosaccharides were investigated by fluorescence at physiological pH. It was found that both boronic acids 1 and 2 have high selectivity and sensitivity for D-fructose with stability constant of 47.2 and 412.9, respectively. The sensor 2 showed a linear response toward D-fructose in the concentration range from 5 × 10(-5) to 10(-1) mol L(-1) with the detection limit of 2 × 10(-5) mol L(-1).

Keywords: boronic acid; chemosensor; fluorene; fluorescence; saccharide.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Boronic Acids / chemistry*
  • Buffers
  • Fluorenes / chemistry*
  • Fluorescence
  • Fluorescent Dyes / chemistry
  • Hydrogen-Ion Concentration
  • Limit of Detection
  • Molecular Probes / chemistry
  • Monosaccharides / analysis*
  • Monosaccharides / metabolism
  • Spectrometry, Fluorescence / methods*

Substances

  • Boronic Acids
  • Buffers
  • Fluorenes
  • Fluorescent Dyes
  • Molecular Probes
  • Monosaccharides
  • fluorene