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Fluorescent sensors for organophosphorus nerve agent mimics

Academic Article
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Overview

related to degree

  • Dale, Trevor, Ph.D. in Chemistry, Scripps Research 2003 - 2008

authors

  • Dale, Trevor
  • Rebek Jr., Julius

publication date

  • April 2006

journal

  • Journal of the American Chemical Society  Journal

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.

subject areas

  • Alcohols
  • Amines
  • Chemical Warfare Agents
  • Cholinesterase Inhibitors
  • Fluorescent Dyes
  • Organophosphorus Compounds
  • Pyrenes
  • Reagent Strips
  • Spectrometry, Fluorescence
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Identity

International Standard Serial Number (ISSN)

  • 0002-7863

Digital Object Identifier (DOI)

  • 10.1021/ja057449i

PubMed ID

  • 16594648
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Additional Document Info

start page

  • 4500

end page

  • 4501

volume

  • 128

issue

  • 14

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