An NIR Emissive Donor-π-Acceptor Dicyanomethylene-4H-Pyran Derivative as a Fluorescent Chemosensor System towards Copper (II) Detection

Detalhes bibliográficos
Autor(a) principal: Karkosik, Agata
Data de Publicação: 2022
Outros Autores: Moro, Artur J.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10362/144743
Resumo: A.K. thanks the Erasmus+ Programme of the European Union for a student mobility fellowship. Publisher Copyright: © 2022 by the authors.
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spelling An NIR Emissive Donor-π-Acceptor Dicyanomethylene-4H-Pyran Derivative as a Fluorescent Chemosensor System towards Copper (II) Detection3,5-diphenyl-dicyanomethylene-4H-pyran (DCM)charge transfer (CT)copper (II)Di-(2-picolyl)amine (DPA)fluorescent sensornear-infrared (NIR)Analytical ChemistryPhysical and Theoretical ChemistryA.K. thanks the Erasmus+ Programme of the European Union for a student mobility fellowship. Publisher Copyright: © 2022 by the authors.A novel donor-π-acceptor fluorescent dye as a chemosensor for Cu2+ ions is herein presented. The fluorophoric core consists of a 3,5-diphenyl-dicyanomethylene-4H-pyran (DCM), with extended styryl chains on positions 2 and 6, bearing terminal di-(2-picolyl)amine (DPA) groups for metal coordination. Optical characterization of the chemosensor dye reveals an absorption maximum at ca. 500 nm and a strong bathochromic shift in the emission, reaching ca. 750 nm in polar solvents. This solvatochromic behavior, which yields very large Stokes shifts (up to ~6700 cm−1), is characteristic of the strong intramolecular Charge Transfer (CT) nature of this chromophoric system. While the chemosensor has demonstrated no changes in its optical properties over a wide pH range (2–12), a strong quenching effect was observed upon Cu2+ coordination, with a 1:1 binding stoichiometry, indicating that only one DPA unit is capable of effectively chelating Cu2+, rendering the second DPA motif inactive. The binding constant was determined to be 7.5 × 107 M−1, indicating a very high sensitivity, and an LOD of 90.1 nM. Competition assays have demonstrated that the chemosensor is highly selective towards Cu2+, even in the presence of excesses of other mono- and di-valent cations. Co2+ and Ni2+ proved to be the strongest interferents, particularly in the luminescent response. Paper test-strips prepared with the embedded sensor showed a fluorometric response in the presence of different copper (II) concentrations, which attested to the potential of this chemosensor to be used in the determination of Cu2+ content in aqueous media, for in-field applications.LAQV@REQUIMTEDQ - Departamento de QuímicaRUNKarkosik, AgataMoro, Artur J.2022-10-14T22:15:07Z2022-08-222022-08-22T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article12application/pdfhttp://hdl.handle.net/10362/144743eng2227-9040PURE: 46667715https://doi.org/10.3390/chemosensors10080343info: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:RCAAP2024-03-11T05:24:36Zoai:run.unl.pt:10362/144743Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T03:51:43.873380Repositório 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 An NIR Emissive Donor-π-Acceptor Dicyanomethylene-4H-Pyran Derivative as a Fluorescent Chemosensor System towards Copper (II) Detection
title An NIR Emissive Donor-π-Acceptor Dicyanomethylene-4H-Pyran Derivative as a Fluorescent Chemosensor System towards Copper (II) Detection
spellingShingle An NIR Emissive Donor-π-Acceptor Dicyanomethylene-4H-Pyran Derivative as a Fluorescent Chemosensor System towards Copper (II) Detection
Karkosik, Agata
3,5-diphenyl-dicyanomethylene-4H-pyran (DCM)
charge transfer (CT)
copper (II)
Di-(2-picolyl)amine (DPA)
fluorescent sensor
near-infrared (NIR)
Analytical Chemistry
Physical and Theoretical Chemistry
title_short An NIR Emissive Donor-π-Acceptor Dicyanomethylene-4H-Pyran Derivative as a Fluorescent Chemosensor System towards Copper (II) Detection
title_full An NIR Emissive Donor-π-Acceptor Dicyanomethylene-4H-Pyran Derivative as a Fluorescent Chemosensor System towards Copper (II) Detection
title_fullStr An NIR Emissive Donor-π-Acceptor Dicyanomethylene-4H-Pyran Derivative as a Fluorescent Chemosensor System towards Copper (II) Detection
title_full_unstemmed An NIR Emissive Donor-π-Acceptor Dicyanomethylene-4H-Pyran Derivative as a Fluorescent Chemosensor System towards Copper (II) Detection
title_sort An NIR Emissive Donor-π-Acceptor Dicyanomethylene-4H-Pyran Derivative as a Fluorescent Chemosensor System towards Copper (II) Detection
author Karkosik, Agata
author_facet Karkosik, Agata
Moro, Artur J.
author_role author
author2 Moro, Artur J.
author2_role author
dc.contributor.none.fl_str_mv LAQV@REQUIMTE
DQ - Departamento de Química
RUN
dc.contributor.author.fl_str_mv Karkosik, Agata
Moro, Artur J.
dc.subject.por.fl_str_mv 3,5-diphenyl-dicyanomethylene-4H-pyran (DCM)
charge transfer (CT)
copper (II)
Di-(2-picolyl)amine (DPA)
fluorescent sensor
near-infrared (NIR)
Analytical Chemistry
Physical and Theoretical Chemistry
topic 3,5-diphenyl-dicyanomethylene-4H-pyran (DCM)
charge transfer (CT)
copper (II)
Di-(2-picolyl)amine (DPA)
fluorescent sensor
near-infrared (NIR)
Analytical Chemistry
Physical and Theoretical Chemistry
description A.K. thanks the Erasmus+ Programme of the European Union for a student mobility fellowship. Publisher Copyright: © 2022 by the authors.
publishDate 2022
dc.date.none.fl_str_mv 2022-10-14T22:15:07Z
2022-08-22
2022-08-22T00:00:00Z
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/10362/144743
url http://hdl.handle.net/10362/144743
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 2227-9040
PURE: 46667715
https://doi.org/10.3390/chemosensors10080343
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 12
application/pdf
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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