Fluorescent sensors for organophosphorus nerve agent mimics

J Am Chem Soc. 2006 Apr 12;128(14):4500-1. doi: 10.1021/ja057449i.

Abstract

We present a small molecule sensor that provides an optical response to the presence of an organophosphorus (OP)-containing nerve agent mimic. The design contains three key features: a primary alcohol, a tertiary amine in close proximity to the alcohol, and a fluorescent group used as the optical readout. In the sensor's rest state, the lone pair of electrons of the basic amine quenches the fluorescence of the nearby fluorophore through photoinduced electron transfer (PET). Exposure to an OP nerve agent mimic triggers phosphorylation of the primary alcohol followed rapidly by an intramolecular substitution reaction as the amine displaces the created phosphate. The quaternized ammonium salt produced by this cyclization reaction no longer possesses a lone pair of electrons, and a fluorescence readout is observed as the nonradiative PET quenching pathway of the fluorophore is shut down.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Alcohols / chemistry
  • Amines / chemistry
  • Chemical Warfare Agents / analysis*
  • Cholinesterase Inhibitors / analysis
  • Fluorescent Dyes / chemical synthesis
  • Fluorescent Dyes / chemistry*
  • Organophosphorus Compounds / analysis*
  • Pyrenes / chemical synthesis
  • Pyrenes / chemistry*
  • Reagent Strips*
  • Spectrometry, Fluorescence

Substances

  • Alcohols
  • Amines
  • Chemical Warfare Agents
  • Cholinesterase Inhibitors
  • Fluorescent Dyes
  • Organophosphorus Compounds
  • Pyrenes
  • Reagent Strips