A Fluorescent Dipyrrinone Oxime for the Detection of Pesticides and Other Organophosphates

Ian Walton; Marauo Davis; Lyndsay Munro; Vincent J. Catalano; Peter J. Cragg; Michael T. Huggins; Karl J. Wallace

doi:10.1021/ol300799f

A Fluorescent Dipyrrinone Oxime for the Detection of Pesticides and Other Organophosphates

Ian Walton, Marauo Davis, Lyndsay Munro, Vincent J. Catalano, Peter J. Cragg, Michael T. Huggins, Karl J. Wallace

Biochemistry, Chemistry & Physics

Research output: Contribution to journal › Article › peer-review

80 Scopus citations

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.

Original language	English
Pages (from-to)	2686-2689
Number of pages	4
Journal	Organic Letters
Volume	14
Issue number	11
DOIs	https://doi.org/10.1021/ol300799f
State	Published - Jun 1 2012

Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

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10.1021/ol300799f

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AU - Walton, Ian

AU - Davis, Marauo

AU - Munro, Lyndsay

AU - Catalano, Vincent J.

AU - Cragg, Peter J.

AU - Huggins, Michael T.

AU - Wallace, Karl J.

PY - 2012/6/1

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AB - 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.

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A Fluorescent Dipyrrinone Oxime for the Detection of Pesticides and Other Organophosphates

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