Red-Emitting Polymerizable Guanidinium Dyes as Fluorescent Probes in Molecularly Imprinted Polymers for Glyphosate Detection

The development of methodologies to sense glyphosate has gained momentum due to its toxicological and ecotoxicological effects. In this work, a red-emitting and polymerizable guanidinium benzoxadiazole probe was developed for the fluorescence detection of glyphosate. The interaction of the fluoresce...

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Main Authors: Martha Kimani, Víctor Pérez-Padilla, Virginia Valderrey, Kornelia Gawlitza, Knut Rurack
Format: Article
Language:English
Published: MDPI AG 2022-03-01
Series:Chemosensors
Subjects:
Online Access:https://www.mdpi.com/2227-9040/10/3/99
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author Martha Kimani
Víctor Pérez-Padilla
Virginia Valderrey
Kornelia Gawlitza
Knut Rurack
author_facet Martha Kimani
Víctor Pérez-Padilla
Virginia Valderrey
Kornelia Gawlitza
Knut Rurack
author_sort Martha Kimani
collection DOAJ
description The development of methodologies to sense glyphosate has gained momentum due to its toxicological and ecotoxicological effects. In this work, a red-emitting and polymerizable guanidinium benzoxadiazole probe was developed for the fluorescence detection of glyphosate. The interaction of the fluorescent probe and the tetrabutylammonium salt of glyphosate was studied via UV/vis absorption and fluorescence spectroscopy in chloroform and acetonitrile. The selective recognition of glyphosate was achieved by preparing molecularly imprinted polymers, able to discriminate against other common herbicides such as 2,4-dichlorophenoxyacetic acid (2,4-D) and 3,6-dichloro-2-methoxybenzoic acid (dicamba), as thin layers on submicron silica particles. The limits of detection of 4.8 µM and 0.6 µM were obtained for the sensing of glyphosate in chloroform and acetonitrile, respectively. The reported system shows promise for future application in the sensing of glyphosate through further optimization of the dye and the implementation of a biphasic assay with water/organic solvent mixtures for sensing in aqueous environmental samples.
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spelling doaj.art-ba7c1f922cfc446d92121b9e7e25a5a52023-11-24T00:45:51ZengMDPI AGChemosensors2227-90402022-03-011039910.3390/chemosensors10030099Red-Emitting Polymerizable Guanidinium Dyes as Fluorescent Probes in Molecularly Imprinted Polymers for Glyphosate DetectionMartha Kimani0Víctor Pérez-Padilla1Virginia Valderrey2Kornelia Gawlitza3Knut Rurack4Chemical and Optical Sensing Division, Bundesanstalt für Materialforschung und-prüfung (BAM), Richard-Willstätter Straße 11, 12489 Berlin, GermanyChemical and Optical Sensing Division, Bundesanstalt für Materialforschung und-prüfung (BAM), Richard-Willstätter Straße 11, 12489 Berlin, GermanyChemical and Optical Sensing Division, Bundesanstalt für Materialforschung und-prüfung (BAM), Richard-Willstätter Straße 11, 12489 Berlin, GermanyChemical and Optical Sensing Division, Bundesanstalt für Materialforschung und-prüfung (BAM), Richard-Willstätter Straße 11, 12489 Berlin, GermanyChemical and Optical Sensing Division, Bundesanstalt für Materialforschung und-prüfung (BAM), Richard-Willstätter Straße 11, 12489 Berlin, GermanyThe development of methodologies to sense glyphosate has gained momentum due to its toxicological and ecotoxicological effects. In this work, a red-emitting and polymerizable guanidinium benzoxadiazole probe was developed for the fluorescence detection of glyphosate. The interaction of the fluorescent probe and the tetrabutylammonium salt of glyphosate was studied via UV/vis absorption and fluorescence spectroscopy in chloroform and acetonitrile. The selective recognition of glyphosate was achieved by preparing molecularly imprinted polymers, able to discriminate against other common herbicides such as 2,4-dichlorophenoxyacetic acid (2,4-D) and 3,6-dichloro-2-methoxybenzoic acid (dicamba), as thin layers on submicron silica particles. The limits of detection of 4.8 µM and 0.6 µM were obtained for the sensing of glyphosate in chloroform and acetonitrile, respectively. The reported system shows promise for future application in the sensing of glyphosate through further optimization of the dye and the implementation of a biphasic assay with water/organic solvent mixtures for sensing in aqueous environmental samples.https://www.mdpi.com/2227-9040/10/3/99glyphosateguanidinium receptorsfluorescent probesmolecularly imprinted polymerscore-shell particles
spellingShingle Martha Kimani
Víctor Pérez-Padilla
Virginia Valderrey
Kornelia Gawlitza
Knut Rurack
Red-Emitting Polymerizable Guanidinium Dyes as Fluorescent Probes in Molecularly Imprinted Polymers for Glyphosate Detection
Chemosensors
glyphosate
guanidinium receptors
fluorescent probes
molecularly imprinted polymers
core-shell particles
title Red-Emitting Polymerizable Guanidinium Dyes as Fluorescent Probes in Molecularly Imprinted Polymers for Glyphosate Detection
title_full Red-Emitting Polymerizable Guanidinium Dyes as Fluorescent Probes in Molecularly Imprinted Polymers for Glyphosate Detection
title_fullStr Red-Emitting Polymerizable Guanidinium Dyes as Fluorescent Probes in Molecularly Imprinted Polymers for Glyphosate Detection
title_full_unstemmed Red-Emitting Polymerizable Guanidinium Dyes as Fluorescent Probes in Molecularly Imprinted Polymers for Glyphosate Detection
title_short Red-Emitting Polymerizable Guanidinium Dyes as Fluorescent Probes in Molecularly Imprinted Polymers for Glyphosate Detection
title_sort red emitting polymerizable guanidinium dyes as fluorescent probes in molecularly imprinted polymers for glyphosate detection
topic glyphosate
guanidinium receptors
fluorescent probes
molecularly imprinted polymers
core-shell particles
url https://www.mdpi.com/2227-9040/10/3/99
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AT victorperezpadilla redemittingpolymerizableguanidiniumdyesasfluorescentprobesinmolecularlyimprintedpolymersforglyphosatedetection
AT virginiavalderrey redemittingpolymerizableguanidiniumdyesasfluorescentprobesinmolecularlyimprintedpolymersforglyphosatedetection
AT korneliagawlitza redemittingpolymerizableguanidiniumdyesasfluorescentprobesinmolecularlyimprintedpolymersforglyphosatedetection
AT knutrurack redemittingpolymerizableguanidiniumdyesasfluorescentprobesinmolecularlyimprintedpolymersforglyphosatedetection