BINOL-based fluorescent sensor for recognition of Cu(II) and sulfide anion in water

J Org Chem. 2012 Sep 21;77(18):8350-4. doi: 10.1021/jo301196m. Epub 2012 Aug 29.

Abstract

A multifunctional fluorescent sensor based on a cyclen-appended BINOL derivative (R-1) was synthesized and characterized. It can display on-off-type fluorescence change with high selectivity toward Cu(II) among 19 metal ions in 100% aqueous solution. Furthermore, the in situ generated R-1-Cu(II) ensemble could recover the quenched fluorescence upon the addition of sulfide anion resulting in a off-on-type sensing with a detection limit of micromolar range in the same medium. No interference was observed from other biothiols and anions, including GSH, l-Cys, DTT, and sulfates, making it a highly sensitive and selective sulfide probe.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anions / chemistry*
  • Copper / chemistry*
  • Fluorescence
  • Molecular Structure
  • Naphthols / chemistry*
  • Spectrometry, Fluorescence
  • Sulfhydryl Compounds / chemistry*
  • Sulfides / chemistry*
  • Water

Substances

  • Anions
  • BINOL, naphthol
  • Naphthols
  • Sulfhydryl Compounds
  • Sulfides
  • Water
  • Copper