Substituted P-Phenylene Ethynylene trimers as fluorescent sensors for nitroaromatic explosives

Detalhes bibliográficos
Autor(a) principal: Costa, Alexandra
Data de Publicação: 2012
Outros Autores: Prata, José Virgílio
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10400.21/5125
Resumo: New sensory materials based on p-phenylene ethynylene trimers integrating calix[4]arene receptors (CALIX-PET) and tert-butylphenol (TBP-PET) moieties have been synthesized and their sensitivity and selectivity for the detection of nitroaromatic compounds (NACs) such as nitrobenzene (NB), 2,4-dinitrotoluene (2,4-DNT), 2,4,6-trinitrotoluene (TNT) and picric acid (PA) investigated in fluid phase and solid-state. It was found that both fluorophores displayed high sensitivities toward NACs detection in solution as evaluated by the Stern-Volmer formalism. For all the tested explosives, the ratio of fluorescence intensities (F-0/F) is a linear function of the quencher concentration only after appropriate correction of fluorescence quenching data for inner-filter effects. The quenching efficiencies for CALIX-PET and TBP-PET follow the order PA >> TNT > DNT > NB, which correlate well with the quenchers electron affinities as evaluated from their LUMOs energies thereby suggesting a photoinduced electron transfer as the dominant mechanism of fluorescence quenching. The selectivity of these sensors was checked against exemplar interferents possessing differentiated electronic properties (benzoic acid, 2,4-dichlorophenol and benzoquinone) and reduced quenching activity was detected. The quenching efficiencies and response times of the two fluorophores in the solid-state toward NB, 2,4-DNT and TNT vapors were evaluated through steady-state fluorescence quenching experiments with the materials dispersed in polymeric matrices or as neat films. The most significant fluorescence quenching responses were achieved for drop-casted films of TBP-PET upon exposure to nitroaromatics.
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spelling Substituted P-Phenylene Ethynylene trimers as fluorescent sensors for nitroaromatic explosivesCalixarenesFluorescenceSensorsp-Phenylene Ethynylene TrimerExplosivesPolymer-filmsConjugated polymersChemical sensorsTNT chemosensorsNew sensory materials based on p-phenylene ethynylene trimers integrating calix[4]arene receptors (CALIX-PET) and tert-butylphenol (TBP-PET) moieties have been synthesized and their sensitivity and selectivity for the detection of nitroaromatic compounds (NACs) such as nitrobenzene (NB), 2,4-dinitrotoluene (2,4-DNT), 2,4,6-trinitrotoluene (TNT) and picric acid (PA) investigated in fluid phase and solid-state. It was found that both fluorophores displayed high sensitivities toward NACs detection in solution as evaluated by the Stern-Volmer formalism. For all the tested explosives, the ratio of fluorescence intensities (F-0/F) is a linear function of the quencher concentration only after appropriate correction of fluorescence quenching data for inner-filter effects. The quenching efficiencies for CALIX-PET and TBP-PET follow the order PA >> TNT > DNT > NB, which correlate well with the quenchers electron affinities as evaluated from their LUMOs energies thereby suggesting a photoinduced electron transfer as the dominant mechanism of fluorescence quenching. The selectivity of these sensors was checked against exemplar interferents possessing differentiated electronic properties (benzoic acid, 2,4-dichlorophenol and benzoquinone) and reduced quenching activity was detected. The quenching efficiencies and response times of the two fluorophores in the solid-state toward NB, 2,4-DNT and TNT vapors were evaluated through steady-state fluorescence quenching experiments with the materials dispersed in polymeric matrices or as neat films. The most significant fluorescence quenching responses were achieved for drop-casted films of TBP-PET upon exposure to nitroaromatics.Elsevier Science SARCIPLCosta, AlexandraPrata, José Virgílio2015-09-08T15:39:54Z2012-01-032012-01-03T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfapplication/pdfhttp://hdl.handle.net/10400.21/5125engCOSTA, A. I.; PRATA, J. V. – Substituted P-Phenylene Ethynylene trimers as fluorescent sensors for nitroaromatic explosives. Sensors and Actuators B-Chemical. ISSN: 0925-4005. Vol. 161, nr. 1 (2012), pp. 251-2600925-400510.1016/j.snb.2011.10.027metadata only accessinfo:eu-repo/semantics/openAccessreponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãoinstacron:RCAAP2023-08-03T09:48:05Zoai:repositorio.ipl.pt:10400.21/5125Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T20:14:26.958529Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informaçãofalse
dc.title.none.fl_str_mv Substituted P-Phenylene Ethynylene trimers as fluorescent sensors for nitroaromatic explosives
title Substituted P-Phenylene Ethynylene trimers as fluorescent sensors for nitroaromatic explosives
spellingShingle Substituted P-Phenylene Ethynylene trimers as fluorescent sensors for nitroaromatic explosives
Costa, Alexandra
Calixarenes
Fluorescence
Sensors
p-Phenylene Ethynylene Trimer
Explosives
Polymer-films
Conjugated polymers
Chemical sensors
TNT chemosensors
title_short Substituted P-Phenylene Ethynylene trimers as fluorescent sensors for nitroaromatic explosives
title_full Substituted P-Phenylene Ethynylene trimers as fluorescent sensors for nitroaromatic explosives
title_fullStr Substituted P-Phenylene Ethynylene trimers as fluorescent sensors for nitroaromatic explosives
title_full_unstemmed Substituted P-Phenylene Ethynylene trimers as fluorescent sensors for nitroaromatic explosives
title_sort Substituted P-Phenylene Ethynylene trimers as fluorescent sensors for nitroaromatic explosives
author Costa, Alexandra
author_facet Costa, Alexandra
Prata, José Virgílio
author_role author
author2 Prata, José Virgílio
author2_role author
dc.contributor.none.fl_str_mv RCIPL
dc.contributor.author.fl_str_mv Costa, Alexandra
Prata, José Virgílio
dc.subject.por.fl_str_mv Calixarenes
Fluorescence
Sensors
p-Phenylene Ethynylene Trimer
Explosives
Polymer-films
Conjugated polymers
Chemical sensors
TNT chemosensors
topic Calixarenes
Fluorescence
Sensors
p-Phenylene Ethynylene Trimer
Explosives
Polymer-films
Conjugated polymers
Chemical sensors
TNT chemosensors
description New sensory materials based on p-phenylene ethynylene trimers integrating calix[4]arene receptors (CALIX-PET) and tert-butylphenol (TBP-PET) moieties have been synthesized and their sensitivity and selectivity for the detection of nitroaromatic compounds (NACs) such as nitrobenzene (NB), 2,4-dinitrotoluene (2,4-DNT), 2,4,6-trinitrotoluene (TNT) and picric acid (PA) investigated in fluid phase and solid-state. It was found that both fluorophores displayed high sensitivities toward NACs detection in solution as evaluated by the Stern-Volmer formalism. For all the tested explosives, the ratio of fluorescence intensities (F-0/F) is a linear function of the quencher concentration only after appropriate correction of fluorescence quenching data for inner-filter effects. The quenching efficiencies for CALIX-PET and TBP-PET follow the order PA >> TNT > DNT > NB, which correlate well with the quenchers electron affinities as evaluated from their LUMOs energies thereby suggesting a photoinduced electron transfer as the dominant mechanism of fluorescence quenching. The selectivity of these sensors was checked against exemplar interferents possessing differentiated electronic properties (benzoic acid, 2,4-dichlorophenol and benzoquinone) and reduced quenching activity was detected. The quenching efficiencies and response times of the two fluorophores in the solid-state toward NB, 2,4-DNT and TNT vapors were evaluated through steady-state fluorescence quenching experiments with the materials dispersed in polymeric matrices or as neat films. The most significant fluorescence quenching responses were achieved for drop-casted films of TBP-PET upon exposure to nitroaromatics.
publishDate 2012
dc.date.none.fl_str_mv 2012-01-03
2012-01-03T00:00:00Z
2015-09-08T15:39:54Z
dc.type.status.fl_str_mv info:eu-repo/semantics/publishedVersion
dc.type.driver.fl_str_mv info:eu-repo/semantics/article
format article
status_str publishedVersion
dc.identifier.uri.fl_str_mv http://hdl.handle.net/10400.21/5125
url http://hdl.handle.net/10400.21/5125
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv COSTA, A. I.; PRATA, J. V. – Substituted P-Phenylene Ethynylene trimers as fluorescent sensors for nitroaromatic explosives. Sensors and Actuators B-Chemical. ISSN: 0925-4005. Vol. 161, nr. 1 (2012), pp. 251-260
0925-4005
10.1016/j.snb.2011.10.027
dc.rights.driver.fl_str_mv metadata only access
info:eu-repo/semantics/openAccess
rights_invalid_str_mv metadata only access
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier Science SA
publisher.none.fl_str_mv Elsevier Science SA
dc.source.none.fl_str_mv reponame:Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
instname:Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron:RCAAP
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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reponame_str Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
collection Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
repository.name.fl_str_mv Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
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