A water-soluble bithiophene with increased photoluminescence efficiency and metal recognition ability

Detalhes bibliográficos
Autor(a) principal: Delgado-Pinar, Estefanía
Data de Publicação: 2020
Outros Autores: Pineiro, Marta, Melo, J. Sérgio Seixas de
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10316/93141
https://doi.org/10.1039/d0dt01385d
Resumo: A new water-soluble tri-tert-butyl-bithiophenesulfonamide (α2-tbS) was synthesized and a comprehensive spectroscopic and photophysical study was undertaken in organic solvents and water at different pH values. In contrast to the behaviour found for the parent (and un-substituted) α,α'-bithiophene (α2), in which radiationless decay processes are the main excited-state deactivation channels, the tert-butylsulfonamide derivative presents a significant fluorescence quantum yield (φF) (ca. one order of magnitude higher than that of α2). The high φF allowed further exploring α2-tbS as a selective fluorimetric sensor for metal ions. A strong selectivity towards Cu(ii) is observed at neutral pH values, whereas at pH = 9.5 a strong quenching upon the addition of Hg(ii) is observed. An additional high sensitivity of 0.64 ± 0.02 ppm towards Cu(ii) was observed, well below 1.25 ppm (∼20 μM), the maximum value allowed in drinking water by the EPA.
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spelling A water-soluble bithiophene with increased photoluminescence efficiency and metal recognition abilityA new water-soluble tri-tert-butyl-bithiophenesulfonamide (α2-tbS) was synthesized and a comprehensive spectroscopic and photophysical study was undertaken in organic solvents and water at different pH values. In contrast to the behaviour found for the parent (and un-substituted) α,α'-bithiophene (α2), in which radiationless decay processes are the main excited-state deactivation channels, the tert-butylsulfonamide derivative presents a significant fluorescence quantum yield (φF) (ca. one order of magnitude higher than that of α2). The high φF allowed further exploring α2-tbS as a selective fluorimetric sensor for metal ions. A strong selectivity towards Cu(ii) is observed at neutral pH values, whereas at pH = 9.5 a strong quenching upon the addition of Hg(ii) is observed. An additional high sensitivity of 0.64 ± 0.02 ppm towards Cu(ii) was observed, well below 1.25 ppm (∼20 μM), the maximum value allowed in drinking water by the EPA.Royal Society of Chemistry2020-09-15info:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articlehttp://hdl.handle.net/10316/93141http://hdl.handle.net/10316/93141https://doi.org/10.1039/d0dt01385deng1477-92341477-9226https://pubs.rsc.org/en/content/articlelanding/2020/DT/D0DT01385DDelgado-Pinar, EstefaníaPineiro, MartaMelo, J. Sérgio Seixas deinfo: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:RCAAP2022-05-25T06:08:43Zoai:estudogeral.uc.pt:10316/93141Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T21:12:07.396072Repositório 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 A water-soluble bithiophene with increased photoluminescence efficiency and metal recognition ability
title A water-soluble bithiophene with increased photoluminescence efficiency and metal recognition ability
spellingShingle A water-soluble bithiophene with increased photoluminescence efficiency and metal recognition ability
Delgado-Pinar, Estefanía
title_short A water-soluble bithiophene with increased photoluminescence efficiency and metal recognition ability
title_full A water-soluble bithiophene with increased photoluminescence efficiency and metal recognition ability
title_fullStr A water-soluble bithiophene with increased photoluminescence efficiency and metal recognition ability
title_full_unstemmed A water-soluble bithiophene with increased photoluminescence efficiency and metal recognition ability
title_sort A water-soluble bithiophene with increased photoluminescence efficiency and metal recognition ability
author Delgado-Pinar, Estefanía
author_facet Delgado-Pinar, Estefanía
Pineiro, Marta
Melo, J. Sérgio Seixas de
author_role author
author2 Pineiro, Marta
Melo, J. Sérgio Seixas de
author2_role author
author
dc.contributor.author.fl_str_mv Delgado-Pinar, Estefanía
Pineiro, Marta
Melo, J. Sérgio Seixas de
description A new water-soluble tri-tert-butyl-bithiophenesulfonamide (α2-tbS) was synthesized and a comprehensive spectroscopic and photophysical study was undertaken in organic solvents and water at different pH values. In contrast to the behaviour found for the parent (and un-substituted) α,α'-bithiophene (α2), in which radiationless decay processes are the main excited-state deactivation channels, the tert-butylsulfonamide derivative presents a significant fluorescence quantum yield (φF) (ca. one order of magnitude higher than that of α2). The high φF allowed further exploring α2-tbS as a selective fluorimetric sensor for metal ions. A strong selectivity towards Cu(ii) is observed at neutral pH values, whereas at pH = 9.5 a strong quenching upon the addition of Hg(ii) is observed. An additional high sensitivity of 0.64 ± 0.02 ppm towards Cu(ii) was observed, well below 1.25 ppm (∼20 μM), the maximum value allowed in drinking water by the EPA.
publishDate 2020
dc.date.none.fl_str_mv 2020-09-15
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/10316/93141
http://hdl.handle.net/10316/93141
https://doi.org/10.1039/d0dt01385d
url http://hdl.handle.net/10316/93141
https://doi.org/10.1039/d0dt01385d
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 1477-9234
1477-9226
https://pubs.rsc.org/en/content/articlelanding/2020/DT/D0DT01385D
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
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
instname_str Agência para a Sociedade do Conhecimento (UMIC) - FCT - Sociedade da Informação
instacron_str RCAAP
institution RCAAP
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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