Novel functionalised imidazo-benzocrown ethers bearing a thiophene spacer as fluorimetric chemosensors for metal ion detection
Autor(a) principal: | |
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Data de Publicação: | 2016 |
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/1822/49071 |
Resumo: | Novel phenylalanine derivatives bearing benzimidazole and crown ethers as coordinating/reporting units and thiophene as a spacer unit were synthesized for the first time, and their evaluation as fluorimetric chemosensors was carried out in acetonitrile and acetonitrile/water solutions. 15-Crown-5 benzimidazolyl phenylalanine methyl ester, 15-crown-5 thienylbenzimidazolyl phenylalanine methyl ester and 18-crown-6 thienylbenzimidazolyl phenylalanine methyl ester were tested for alkaline, alkaline-earth and transition metal ions (such as Na+, Ca2+, Cd2+, Co2+, Cr3+, Cu2+, Fe2+, Fe3+, Hg2+, Ni2+, Pd2+ and Zn2+). The different crown ether binding moieties as well as the electronic nature and the length of the π-bridge linked to the benzimidazole heterocycle allowed the fine tuning of the sensory properties as seen by spectrofluorimetric titrations. Therefore, 15-crown-5 benzimidazolyl phenylalanine methyl ester is a fluorimetric chemosensor, being selective and sensitive for Cu2+ and Pd2+ in aqueous solutions (ACN/H2O; 80:20). On the other hand, the metal cation sensing properties displayed by 15-crown-5 thienylbenzimidazolyl phenylalanine methyl ester bearing an arylthienyl spacer showed that this is a promising candidate as fluorimetric chemosensor for Fe3+, Pb2+ and Pd2+ in acetonitrile solution. |
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Novel functionalised imidazo-benzocrown ethers bearing a thiophene spacer as fluorimetric chemosensors for metal ion detectionPhenylalanineImidazo-benzocrown etherThiopheneFluorescenceMetal ion detectionAqueous solutionCiências Naturais::Ciências QuímicasScience & TechnologyNovel phenylalanine derivatives bearing benzimidazole and crown ethers as coordinating/reporting units and thiophene as a spacer unit were synthesized for the first time, and their evaluation as fluorimetric chemosensors was carried out in acetonitrile and acetonitrile/water solutions. 15-Crown-5 benzimidazolyl phenylalanine methyl ester, 15-crown-5 thienylbenzimidazolyl phenylalanine methyl ester and 18-crown-6 thienylbenzimidazolyl phenylalanine methyl ester were tested for alkaline, alkaline-earth and transition metal ions (such as Na+, Ca2+, Cd2+, Co2+, Cr3+, Cu2+, Fe2+, Fe3+, Hg2+, Ni2+, Pd2+ and Zn2+). The different crown ether binding moieties as well as the electronic nature and the length of the π-bridge linked to the benzimidazole heterocycle allowed the fine tuning of the sensory properties as seen by spectrofluorimetric titrations. Therefore, 15-crown-5 benzimidazolyl phenylalanine methyl ester is a fluorimetric chemosensor, being selective and sensitive for Cu2+ and Pd2+ in aqueous solutions (ACN/H2O; 80:20). On the other hand, the metal cation sensing properties displayed by 15-crown-5 thienylbenzimidazolyl phenylalanine methyl ester bearing an arylthienyl spacer showed that this is a promising candidate as fluorimetric chemosensor for Fe3+, Pb2+ and Pd2+ in acetonitrile solution.Thanks are due to Fundação para a Ciência e Tecnologia (Portugal) for financial support to the Portuguese NMR network (PTNMR, Bruker Avance III 400-Univ. Minho), FCT and FEDER (European Fund for Regional Development)-COMPETEQREN-EU for financial support to the research centre CQ/UM [PEst-C/QUI/UI0686/2013 (FCOMP-01-0124-FEDER-037302], a PhD grant to C.I.C. Esteves (SFRH/BD/68360/2010) and a post-doctoral grant to R.M.F. Batista (SFRH/BPD/79333/2011).info:eu-repo/semantics/publishedVersionElsevierUniversidade do MinhoEsteves, Cátia Isabel CanavezesBatista, Rosa Maria FerreiraRaposo, M. Manuela M.Costa, Susana P. G.2016-042016-04-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/1822/49071engDyes and Pigments, 2016, 135, 134-1420143-72081873-374310.1016/j.dyepig.2016.04.037https://doi.org/10.1016/j.dyepig.2016.04.037info: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:RCAAP2023-07-21T12:03:39ZPortal AgregadorONG |
dc.title.none.fl_str_mv |
Novel functionalised imidazo-benzocrown ethers bearing a thiophene spacer as fluorimetric chemosensors for metal ion detection |
title |
Novel functionalised imidazo-benzocrown ethers bearing a thiophene spacer as fluorimetric chemosensors for metal ion detection |
spellingShingle |
Novel functionalised imidazo-benzocrown ethers bearing a thiophene spacer as fluorimetric chemosensors for metal ion detection Esteves, Cátia Isabel Canavezes Phenylalanine Imidazo-benzocrown ether Thiophene Fluorescence Metal ion detection Aqueous solution Ciências Naturais::Ciências Químicas Science & Technology |
title_short |
Novel functionalised imidazo-benzocrown ethers bearing a thiophene spacer as fluorimetric chemosensors for metal ion detection |
title_full |
Novel functionalised imidazo-benzocrown ethers bearing a thiophene spacer as fluorimetric chemosensors for metal ion detection |
title_fullStr |
Novel functionalised imidazo-benzocrown ethers bearing a thiophene spacer as fluorimetric chemosensors for metal ion detection |
title_full_unstemmed |
Novel functionalised imidazo-benzocrown ethers bearing a thiophene spacer as fluorimetric chemosensors for metal ion detection |
title_sort |
Novel functionalised imidazo-benzocrown ethers bearing a thiophene spacer as fluorimetric chemosensors for metal ion detection |
author |
Esteves, Cátia Isabel Canavezes |
author_facet |
Esteves, Cátia Isabel Canavezes Batista, Rosa Maria Ferreira Raposo, M. Manuela M. Costa, Susana P. G. |
author_role |
author |
author2 |
Batista, Rosa Maria Ferreira Raposo, M. Manuela M. Costa, Susana P. G. |
author2_role |
author author author |
dc.contributor.none.fl_str_mv |
Universidade do Minho |
dc.contributor.author.fl_str_mv |
Esteves, Cátia Isabel Canavezes Batista, Rosa Maria Ferreira Raposo, M. Manuela M. Costa, Susana P. G. |
dc.subject.por.fl_str_mv |
Phenylalanine Imidazo-benzocrown ether Thiophene Fluorescence Metal ion detection Aqueous solution Ciências Naturais::Ciências Químicas Science & Technology |
topic |
Phenylalanine Imidazo-benzocrown ether Thiophene Fluorescence Metal ion detection Aqueous solution Ciências Naturais::Ciências Químicas Science & Technology |
description |
Novel phenylalanine derivatives bearing benzimidazole and crown ethers as coordinating/reporting units and thiophene as a spacer unit were synthesized for the first time, and their evaluation as fluorimetric chemosensors was carried out in acetonitrile and acetonitrile/water solutions. 15-Crown-5 benzimidazolyl phenylalanine methyl ester, 15-crown-5 thienylbenzimidazolyl phenylalanine methyl ester and 18-crown-6 thienylbenzimidazolyl phenylalanine methyl ester were tested for alkaline, alkaline-earth and transition metal ions (such as Na+, Ca2+, Cd2+, Co2+, Cr3+, Cu2+, Fe2+, Fe3+, Hg2+, Ni2+, Pd2+ and Zn2+). The different crown ether binding moieties as well as the electronic nature and the length of the π-bridge linked to the benzimidazole heterocycle allowed the fine tuning of the sensory properties as seen by spectrofluorimetric titrations. Therefore, 15-crown-5 benzimidazolyl phenylalanine methyl ester is a fluorimetric chemosensor, being selective and sensitive for Cu2+ and Pd2+ in aqueous solutions (ACN/H2O; 80:20). On the other hand, the metal cation sensing properties displayed by 15-crown-5 thienylbenzimidazolyl phenylalanine methyl ester bearing an arylthienyl spacer showed that this is a promising candidate as fluorimetric chemosensor for Fe3+, Pb2+ and Pd2+ in acetonitrile solution. |
publishDate |
2016 |
dc.date.none.fl_str_mv |
2016-04 2016-04-01T00:00:00Z |
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/1822/49071 |
url |
http://hdl.handle.net/1822/49071 |
dc.language.iso.fl_str_mv |
eng |
language |
eng |
dc.relation.none.fl_str_mv |
Dyes and Pigments, 2016, 135, 134-142 0143-7208 1873-3743 10.1016/j.dyepig.2016.04.037 https://doi.org/10.1016/j.dyepig.2016.04.037 |
dc.rights.driver.fl_str_mv |
info:eu-repo/semantics/openAccess |
eu_rights_str_mv |
openAccess |
dc.format.none.fl_str_mv |
application/pdf |
dc.publisher.none.fl_str_mv |
Elsevier |
publisher.none.fl_str_mv |
Elsevier |
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 |
instacron_str |
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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