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

84 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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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.",

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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

Y1 - 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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ER -

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

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