A fluorescent dipyrrinone oxime for the detection of pesticides and other organophosphates

Org Lett. 2012 Jun 1;14(11):2686-9. doi: 10.1021/ol300799f. Epub 2012 May 18.

Abstract

An N,N-carbonyl-bridged dipyrrinone oxime has been synthesized and studied as a potential sensor for organophosphates. The molecular sensor underwent a drastic colorimetric response upon formation of the adduct. The pesticide dimethoate was found to produce the biggest spectral response, with a limit of detection equal to 4.0 ppm using UV-visible spectroscopy. Minimal fluorescence "turn on" via a PET mechanism was seen, and molecular modeling studies were used to explain the lower than expected PET response. The X-ray crystal structure of the fluorescent dipyrrinone oxime was also obtained.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Coloring Agents
  • Fluorescent Dyes / chemical synthesis*
  • Fluorescent Dyes / chemistry
  • Models, Molecular*
  • Molecular Structure
  • Organophosphates / analysis
  • Organophosphates / chemistry*
  • Oximes / chemical synthesis*
  • Oximes / chemistry
  • Pesticides / analysis
  • Pesticides / chemistry*
  • Positron-Emission Tomography

Substances

  • Coloring Agents
  • Fluorescent Dyes
  • Organophosphates
  • Oximes
  • Pesticides