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Sulfonamide-imines as selective fluorescent chemosensors for the fluoride anion

Two new sulfonamide-type fluorescent chemosensors in organic media are reported. The two receptors, [ N , N ′-bis(2-tosylaminobenzylidene)-1,2-diaminoethane and N , N ′-bis(2-tosylaminobenzylidene)-1,3-diamino-2-propanol], display marked changes in the fluorescence emission intensities as a result o... Full description

Journal Title: Organic & Biomolecular Chemistry 2009, Vol.8(2), pp.357-362
Main Author: López, Miguel Vázquez
Other Authors: Bermejo, Manuel R. , Vázquez, M. Eugenio , Taglietti, Angelo , Zaragoza, Guillermo , Pedrido, Rosa , Martínez-calvo, Miguel
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ID: ISSN: 1477-0520 ; E-ISSN: 1477-0539 ; DOI: 10.1039/b916040j
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recordid: rscb916040j
title: Sulfonamide-imines as selective fluorescent chemosensors for the fluoride anion
format: Article
creator:
  • López, Miguel Vázquez
  • Bermejo, Manuel R.
  • Vázquez, M. Eugenio
  • Taglietti, Angelo
  • Zaragoza, Guillermo
  • Pedrido, Rosa
  • Martínez-calvo, Miguel
subjects:
  • Fluorescent Dyes -- Chemistry
  • Fluorides -- Analysis
  • Imines -- Chemistry
  • Sulfonamides -- Chemistry
ispartof: Organic & Biomolecular Chemistry, 2009, Vol.8(2), pp.357-362
description: Two new sulfonamide-type fluorescent chemosensors in organic media are reported. The two receptors, [ N , N ′-bis(2-tosylaminobenzylidene)-1,2-diaminoethane and N , N ′-bis(2-tosylaminobenzylidene)-1,3-diamino-2-propanol], display marked changes in the fluorescence emission intensities as a result of deprotonation by basic anions, and show high selectivity for fluoride over other inorganic anions, such as acetate or dihydrogenphosphate. These results suggest that the presence of the imine group as an intramolecular H-bond acceptor enhances the selectivity of these sensors compared to previous examples in the literature. The deprotonation mechanism has been demonstrated by spectrophotometric and spectrofluorimetric titrations as well as by NMR spectroscopy. The X-ray structures of both receptors are also discussed.
language:
source:
identifier: ISSN: 1477-0520 ; E-ISSN: 1477-0539 ; DOI: 10.1039/b916040j
fulltext: fulltext
issn:
  • 14770539
  • 1477-0539
  • 14770520
  • 1477-0520
url: Link


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titleSulfonamide-imines as selective fluorescent chemosensors for the fluoride anion
creatorLópez, Miguel Vázquez ; Bermejo, Manuel R. ; Vázquez, M. Eugenio ; Taglietti, Angelo ; Zaragoza, Guillermo ; Pedrido, Rosa ; Martínez-calvo, Miguel
ispartofOrganic & Biomolecular Chemistry, 2009, Vol.8(2), pp.357-362
identifier
descriptionTwo new sulfonamide-type fluorescent chemosensors in organic media are reported. The two receptors, [ N , N ′-bis(2-tosylaminobenzylidene)-1,2-diaminoethane and N , N ′-bis(2-tosylaminobenzylidene)-1,3-diamino-2-propanol], display marked changes in the fluorescence emission intensities as a result of deprotonation by basic anions, and show high selectivity for fluoride over other inorganic anions, such as acetate or dihydrogenphosphate. These results suggest that the presence of the imine group as an intramolecular H-bond acceptor enhances the selectivity of these sensors compared to previous examples in the literature. The deprotonation mechanism has been demonstrated by spectrophotometric and spectrofluorimetric titrations as well as by NMR spectroscopy. The X-ray structures of both receptors are also discussed.
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subjectFluorescent Dyes -- Chemistry ; Fluorides -- Analysis ; Imines -- Chemistry ; Sulfonamides -- Chemistry;
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titleSulfonamide-imines as selective fluorescent chemosensors for the fluoride anion
descriptionTwo new sulfonamide-type fluorescent chemosensors in organic media are reported. The two receptors, [ N , N ′-bis(2-tosylaminobenzylidene)-1,2-diaminoethane and N , N ′-bis(2-tosylaminobenzylidene)-1,3-diamino-2-propanol], display marked changes in the fluorescence emission intensities as a result of deprotonation by basic anions, and show high selectivity for fluoride over other inorganic anions, such as acetate or dihydrogenphosphate. These results suggest that the presence of the imine group as an intramolecular H-bond acceptor enhances the selectivity of these sensors compared to previous examples in the literature. The deprotonation mechanism has been demonstrated by spectrophotometric and spectrofluorimetric titrations as well as by NMR spectroscopy. The X-ray structures of both receptors are also discussed.
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abstractTwo new sulfonamide-type fluorescent chemosensors in organic media are reported. The two receptors, [ N , N ′-bis(2-tosylaminobenzylidene)-1,2-diaminoethane and N , N ′-bis(2-tosylaminobenzylidene)-1,3-diamino-2-propanol], display marked changes in the fluorescence emission intensities as a result of deprotonation by basic anions, and show high selectivity for fluoride over other inorganic anions, such as acetate or dihydrogenphosphate. These results suggest that the presence of the imine group as an intramolecular H-bond acceptor enhances the selectivity of these sensors compared to previous examples in the literature. The deprotonation mechanism has been demonstrated by spectrophotometric and spectrofluorimetric titrations as well as by NMR spectroscopy. The X-ray structures of both receptors are also discussed.
doi10.1039/b916040j
pages357-362
date2009-12-23