Synthesis and Photophysical Characterization of Proton Transfer-Based Thiourea Derivatives: Potential Application as Colorimetric Naked-Eye Chemosensor for Fluoride Detection in Solution

Detalhes bibliográficos
Autor(a) principal: Silva,Cláudia B. da
Data de Publicação: 2017
Outros Autores: Kroetz,Thais, Santos,Fabiano S., Rodembusch,Fabiano S.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Journal of the Brazilian Chemical Society (Online)
Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017000901830
Resumo: Two new thiourea derivatives were synthesized through the reaction of photoactive aminohydroxybenzazoles and p-isothiocyanate benzoic acid via nucleophilic addition reaction. The compounds were characterized using high resolution mass spectrometry with eletrospray ionization (HRMS-ESI), Fourier transform infrared (FTIR), 13C and 1H nuclear magnetic resonance (NMR) spectroscopies. UV-Vis and steady-state fluorescence in solution were also applied to characterize their photophysical behavior. The compounds present absorption in the ultraviolet region (ca. 300 nm) and fluorescence emission with a large Stokes' shift in the UV-A and green region, with the longer wavelength related to phototautomerism in the excited state (ESIPT). Both compounds were investigated as optical sensors for the detection of anions in solution, presenting a potential application for fluoride ion detection by naked-eye and UV-Vis spectroscopy. The continuous variation method plot gave a 1:1 stoichiometric ratio between the chemosensors and F- for the new formed species. The UV-Vis and 1H NMR titration experiments reflect the establishment of a hydrogen bond interaction between the thiourea moiety of the chemosensors and fluoride. In addition, the presence of fluoride in solution tailored the fluorescence emission of one compound favoring the ESIPT emission.
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spelling Synthesis and Photophysical Characterization of Proton Transfer-Based Thiourea Derivatives: Potential Application as Colorimetric Naked-Eye Chemosensor for Fluoride Detection in SolutionESIPToptical sensorsbenzazolesfluoride ionfluorescenceTwo new thiourea derivatives were synthesized through the reaction of photoactive aminohydroxybenzazoles and p-isothiocyanate benzoic acid via nucleophilic addition reaction. The compounds were characterized using high resolution mass spectrometry with eletrospray ionization (HRMS-ESI), Fourier transform infrared (FTIR), 13C and 1H nuclear magnetic resonance (NMR) spectroscopies. UV-Vis and steady-state fluorescence in solution were also applied to characterize their photophysical behavior. The compounds present absorption in the ultraviolet region (ca. 300 nm) and fluorescence emission with a large Stokes' shift in the UV-A and green region, with the longer wavelength related to phototautomerism in the excited state (ESIPT). Both compounds were investigated as optical sensors for the detection of anions in solution, presenting a potential application for fluoride ion detection by naked-eye and UV-Vis spectroscopy. The continuous variation method plot gave a 1:1 stoichiometric ratio between the chemosensors and F- for the new formed species. The UV-Vis and 1H NMR titration experiments reflect the establishment of a hydrogen bond interaction between the thiourea moiety of the chemosensors and fluoride. In addition, the presence of fluoride in solution tailored the fluorescence emission of one compound favoring the ESIPT emission.Sociedade Brasileira de Química2017-09-01info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersiontext/htmlhttp://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017000901830Journal of the Brazilian Chemical Society v.28 n.9 2017reponame:Journal of the Brazilian Chemical Society (Online)instname:Sociedade Brasileira de Química (SBQ)instacron:SBQ10.21577/0103-5053.20170098info:eu-repo/semantics/openAccessSilva,Cláudia B. daKroetz,ThaisSantos,Fabiano S.Rodembusch,Fabiano S.eng2017-07-28T00:00:00Zoai:scielo:S0103-50532017000901830Revistahttp://jbcs.sbq.org.brONGhttps://old.scielo.br/oai/scielo-oai.php||office@jbcs.sbq.org.br1678-47900103-5053opendoar:2017-07-28T00:00Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)false
dc.title.none.fl_str_mv Synthesis and Photophysical Characterization of Proton Transfer-Based Thiourea Derivatives: Potential Application as Colorimetric Naked-Eye Chemosensor for Fluoride Detection in Solution
title Synthesis and Photophysical Characterization of Proton Transfer-Based Thiourea Derivatives: Potential Application as Colorimetric Naked-Eye Chemosensor for Fluoride Detection in Solution
spellingShingle Synthesis and Photophysical Characterization of Proton Transfer-Based Thiourea Derivatives: Potential Application as Colorimetric Naked-Eye Chemosensor for Fluoride Detection in Solution
Silva,Cláudia B. da
ESIPT
optical sensors
benzazoles
fluoride ion
fluorescence
title_short Synthesis and Photophysical Characterization of Proton Transfer-Based Thiourea Derivatives: Potential Application as Colorimetric Naked-Eye Chemosensor for Fluoride Detection in Solution
title_full Synthesis and Photophysical Characterization of Proton Transfer-Based Thiourea Derivatives: Potential Application as Colorimetric Naked-Eye Chemosensor for Fluoride Detection in Solution
title_fullStr Synthesis and Photophysical Characterization of Proton Transfer-Based Thiourea Derivatives: Potential Application as Colorimetric Naked-Eye Chemosensor for Fluoride Detection in Solution
title_full_unstemmed Synthesis and Photophysical Characterization of Proton Transfer-Based Thiourea Derivatives: Potential Application as Colorimetric Naked-Eye Chemosensor for Fluoride Detection in Solution
title_sort Synthesis and Photophysical Characterization of Proton Transfer-Based Thiourea Derivatives: Potential Application as Colorimetric Naked-Eye Chemosensor for Fluoride Detection in Solution
author Silva,Cláudia B. da
author_facet Silva,Cláudia B. da
Kroetz,Thais
Santos,Fabiano S.
Rodembusch,Fabiano S.
author_role author
author2 Kroetz,Thais
Santos,Fabiano S.
Rodembusch,Fabiano S.
author2_role author
author
author
dc.contributor.author.fl_str_mv Silva,Cláudia B. da
Kroetz,Thais
Santos,Fabiano S.
Rodembusch,Fabiano S.
dc.subject.por.fl_str_mv ESIPT
optical sensors
benzazoles
fluoride ion
fluorescence
topic ESIPT
optical sensors
benzazoles
fluoride ion
fluorescence
description Two new thiourea derivatives were synthesized through the reaction of photoactive aminohydroxybenzazoles and p-isothiocyanate benzoic acid via nucleophilic addition reaction. The compounds were characterized using high resolution mass spectrometry with eletrospray ionization (HRMS-ESI), Fourier transform infrared (FTIR), 13C and 1H nuclear magnetic resonance (NMR) spectroscopies. UV-Vis and steady-state fluorescence in solution were also applied to characterize their photophysical behavior. The compounds present absorption in the ultraviolet region (ca. 300 nm) and fluorescence emission with a large Stokes' shift in the UV-A and green region, with the longer wavelength related to phototautomerism in the excited state (ESIPT). Both compounds were investigated as optical sensors for the detection of anions in solution, presenting a potential application for fluoride ion detection by naked-eye and UV-Vis spectroscopy. The continuous variation method plot gave a 1:1 stoichiometric ratio between the chemosensors and F- for the new formed species. The UV-Vis and 1H NMR titration experiments reflect the establishment of a hydrogen bond interaction between the thiourea moiety of the chemosensors and fluoride. In addition, the presence of fluoride in solution tailored the fluorescence emission of one compound favoring the ESIPT emission.
publishDate 2017
dc.date.none.fl_str_mv 2017-09-01
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
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dc.identifier.uri.fl_str_mv http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017000901830
url http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017000901830
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 10.21577/0103-5053.20170098
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
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dc.format.none.fl_str_mv text/html
dc.publisher.none.fl_str_mv Sociedade Brasileira de Química
publisher.none.fl_str_mv Sociedade Brasileira de Química
dc.source.none.fl_str_mv Journal of the Brazilian Chemical Society v.28 n.9 2017
reponame:Journal of the Brazilian Chemical Society (Online)
instname:Sociedade Brasileira de Química (SBQ)
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instname_str Sociedade Brasileira de Química (SBQ)
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reponame_str Journal of the Brazilian Chemical Society (Online)
collection Journal of the Brazilian Chemical Society (Online)
repository.name.fl_str_mv Journal of the Brazilian Chemical Society (Online) - Sociedade Brasileira de Química (SBQ)
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