N,N-Diphenylanilino-heterocyclic aldehyde-based chemosensors for UV-vis/NIR and fluorescence Cu(II) detection
Autor(a) principal: | |
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Data de Publicação: | 2019 |
Outros Autores: | , , , , , , |
Tipo de documento: | Artigo |
Idioma: | eng |
Título da fonte: | Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
Texto Completo: | http://hdl.handle.net/1822/63928 |
Resumo: | Herein, three N,N-diphenylanilino-heterocyclic aldehyde probes (5, 6 and 7) are synthesized, characterized and their sensing behaviour against metal cations tested. Acetonitrile solutions of the three probes show an intramolecular charge-transfer band in the 360-420 nm range due to the presence of an electron donor N,N-diphenylanilino group and an electron acceptor aldehyde moiety. Besides, all three probes are moderately emissive with bands in the 540-580 nm range in acetronitrile. The chromo-fluorogenic behaviour of the three probes in acetonitrile in the presence of selected metal cations is assessed. Of all the metal cations tested only Cu(ii) induces marked colour and emission changes. In this respect, addition of Cu(ii) cations to solutions of the probes induces the appearance of NIR absorptions at 756 nm for 5, at 852 nm for 6 and at 527, 625 and 1072 nm for 7. Besides, Cu(ii) induces a marked quenching of the emission of the three probes. The observed spectral changes are ascribed to the formation of 1:1 probe-Cu(ii) complexes in which the metal cation interacts with the acceptor part of the chemosensors. In addition, the limits of detection determined using UV-visible and fluorescence titrations are in the 0.21-5.12 M range, which are values lower than the minimum concentration prescribed by the World Health Organization (WHO) guideline for drinking water for copper (30 mM). Besides, probe 7 is used for the detection of Cu(ii) in aqueous environments using SDS anionic surfactant. |
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N,N-Diphenylanilino-heterocyclic aldehyde-based chemosensors for UV-vis/NIR and fluorescence Cu(II) detectionScience & TechnologyHerein, three N,N-diphenylanilino-heterocyclic aldehyde probes (5, 6 and 7) are synthesized, characterized and their sensing behaviour against metal cations tested. Acetonitrile solutions of the three probes show an intramolecular charge-transfer band in the 360-420 nm range due to the presence of an electron donor N,N-diphenylanilino group and an electron acceptor aldehyde moiety. Besides, all three probes are moderately emissive with bands in the 540-580 nm range in acetronitrile. The chromo-fluorogenic behaviour of the three probes in acetonitrile in the presence of selected metal cations is assessed. Of all the metal cations tested only Cu(ii) induces marked colour and emission changes. In this respect, addition of Cu(ii) cations to solutions of the probes induces the appearance of NIR absorptions at 756 nm for 5, at 852 nm for 6 and at 527, 625 and 1072 nm for 7. Besides, Cu(ii) induces a marked quenching of the emission of the three probes. The observed spectral changes are ascribed to the formation of 1:1 probe-Cu(ii) complexes in which the metal cation interacts with the acceptor part of the chemosensors. In addition, the limits of detection determined using UV-visible and fluorescence titrations are in the 0.21-5.12 M range, which are values lower than the minimum concentration prescribed by the World Health Organization (WHO) guideline for drinking water for copper (30 mM). Besides, probe 7 is used for the detection of Cu(ii) in aqueous environments using SDS anionic surfactant.We thank the Spanish Government (MAT2015-64139-C4-1-R) and Generalitat Valenciana (PROMETEO2018/024). H. E. O. thanks Generalitat Valenciana for his Grisolia fellowship. Thanks are due to Fundação para a Ciência e Tecnologia (FCT) for a PhD grant to R. C. M. Ferreira (SFRH/BD/86408/2012), and FEDER (European Fund for Regional Development)-COMPETE-QREN-EU for financial support through the Chemistry Research Centre of the University of Minho (Ref. PEst-C/QUI/UI0686/2016 and PEst-C/QUI/UI0686/2018). The NMR spectrometer Bruker Avance III 400 is part of the National NMR Network and was purchased within the framework of the National Program for Scientific Re-equipment, contract REDE/1517/RMN/2005 with funds from POCI 2010 (FEDER) and FCT.Royal Society of ChemistryUniversidade do MinhoOkda, Hazem EssamEl Sayed, SamehFerreira, Rosa Cristina MoutinhoGonçalves, Raquel Costa RaínhaCosta, Susana P. G.Raposo, M. Manuela M.Martínez-Máñez, RamónSancenón, Félix2019-05-212019-05-21T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfapplication/pdfhttp://hdl.handle.net/1822/63928eng1144-05461369-926110.1039/c9nj00880binfo: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:RCAAP2023-07-21T12:45:45Zoai:repositorium.sdum.uminho.pt:1822/63928Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:43:38.940722Repositório 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 |
N,N-Diphenylanilino-heterocyclic aldehyde-based chemosensors for UV-vis/NIR and fluorescence Cu(II) detection |
title |
N,N-Diphenylanilino-heterocyclic aldehyde-based chemosensors for UV-vis/NIR and fluorescence Cu(II) detection |
spellingShingle |
N,N-Diphenylanilino-heterocyclic aldehyde-based chemosensors for UV-vis/NIR and fluorescence Cu(II) detection Okda, Hazem Essam Science & Technology |
title_short |
N,N-Diphenylanilino-heterocyclic aldehyde-based chemosensors for UV-vis/NIR and fluorescence Cu(II) detection |
title_full |
N,N-Diphenylanilino-heterocyclic aldehyde-based chemosensors for UV-vis/NIR and fluorescence Cu(II) detection |
title_fullStr |
N,N-Diphenylanilino-heterocyclic aldehyde-based chemosensors for UV-vis/NIR and fluorescence Cu(II) detection |
title_full_unstemmed |
N,N-Diphenylanilino-heterocyclic aldehyde-based chemosensors for UV-vis/NIR and fluorescence Cu(II) detection |
title_sort |
N,N-Diphenylanilino-heterocyclic aldehyde-based chemosensors for UV-vis/NIR and fluorescence Cu(II) detection |
author |
Okda, Hazem Essam |
author_facet |
Okda, Hazem Essam El Sayed, Sameh Ferreira, Rosa Cristina Moutinho Gonçalves, Raquel Costa Raínha Costa, Susana P. G. Raposo, M. Manuela M. Martínez-Máñez, Ramón Sancenón, Félix |
author_role |
author |
author2 |
El Sayed, Sameh Ferreira, Rosa Cristina Moutinho Gonçalves, Raquel Costa Raínha Costa, Susana P. G. Raposo, M. Manuela M. Martínez-Máñez, Ramón Sancenón, Félix |
author2_role |
author author author author author author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Okda, Hazem Essam El Sayed, Sameh Ferreira, Rosa Cristina Moutinho Gonçalves, Raquel Costa Raínha Costa, Susana P. G. Raposo, M. Manuela M. Martínez-Máñez, Ramón Sancenón, Félix |
dc.subject.por.fl_str_mv |
Science & Technology |
topic |
Science & Technology |
description |
Herein, three N,N-diphenylanilino-heterocyclic aldehyde probes (5, 6 and 7) are synthesized, characterized and their sensing behaviour against metal cations tested. Acetonitrile solutions of the three probes show an intramolecular charge-transfer band in the 360-420 nm range due to the presence of an electron donor N,N-diphenylanilino group and an electron acceptor aldehyde moiety. Besides, all three probes are moderately emissive with bands in the 540-580 nm range in acetronitrile. The chromo-fluorogenic behaviour of the three probes in acetonitrile in the presence of selected metal cations is assessed. Of all the metal cations tested only Cu(ii) induces marked colour and emission changes. In this respect, addition of Cu(ii) cations to solutions of the probes induces the appearance of NIR absorptions at 756 nm for 5, at 852 nm for 6 and at 527, 625 and 1072 nm for 7. Besides, Cu(ii) induces a marked quenching of the emission of the three probes. The observed spectral changes are ascribed to the formation of 1:1 probe-Cu(ii) complexes in which the metal cation interacts with the acceptor part of the chemosensors. In addition, the limits of detection determined using UV-visible and fluorescence titrations are in the 0.21-5.12 M range, which are values lower than the minimum concentration prescribed by the World Health Organization (WHO) guideline for drinking water for copper (30 mM). Besides, probe 7 is used for the detection of Cu(ii) in aqueous environments using SDS anionic surfactant. |
publishDate |
2019 |
dc.date.none.fl_str_mv |
2019-05-21 2019-05-21T00:00:00Z |
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/1822/63928 |
url |
http://hdl.handle.net/1822/63928 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
1144-0546 1369-9261 10.1039/c9nj00880b |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf application/pdf |
dc.publisher.none.fl_str_mv |
Royal Society of Chemistry |
publisher.none.fl_str_mv |
Royal Society of Chemistry |
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 |
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Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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RCAAP |
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RCAAP |
reponame_str |
Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) |
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Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos) - Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação |
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1799132994424799232 |