New dinitrophenyl hydrazones as colorimetric probes for anions

Detalhes bibliográficos
Autor(a) principal: Sousa, Rui P. C. L.
Data de Publicação: 2022
Outros Autores: Costa, Susana P. G., Figueira, Rita B., Raposo, M. Manuela M.
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: https://hdl.handle.net/1822/80385
Resumo: Anion sensing is a dynamic research field due to biological and environmental importance of some organic or inorganic anions. Hydrazones show promising properties in the design of anion chemosensors due to the presence of proton donor and acceptor sites in their structure. In this work, two novel dinitrophenyl hydrazones, functionalized with a quinoline moiety were synthesized and characterized by spectroscopic and spectrometric techniques. The interaction between the new compounds 3a-b with different organic and inorganic anions was assessed. The two compounds showed a change of color from light yellow to magenta in the presence of H2PO4-, CH3COO-, BzO-, CN-, and F-. The interactions were analyzed by spectrophotometric titrations and the stoichiometry of the interaction was assessed by the method of continuous variation. Compound 3b showed a remarkable sensitivity to CN- with a limit of detection of 0.35 µM. The interaction of compound 3b with CN- and F- was also analyzed by 1H NMR titrations showing that increasing concentration of anion induces a deprotonation of NH and OH groups.
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spelling New dinitrophenyl hydrazones as colorimetric probes for anionssynthesisheterocyclesColorimetric probeanionshydrazonequinolinecolorimetric chemosensorCiências Naturais::Ciências QuímicasScience & TechnologySaúde de qualidadeAnion sensing is a dynamic research field due to biological and environmental importance of some organic or inorganic anions. Hydrazones show promising properties in the design of anion chemosensors due to the presence of proton donor and acceptor sites in their structure. In this work, two novel dinitrophenyl hydrazones, functionalized with a quinoline moiety were synthesized and characterized by spectroscopic and spectrometric techniques. The interaction between the new compounds 3a-b with different organic and inorganic anions was assessed. The two compounds showed a change of color from light yellow to magenta in the presence of H2PO4-, CH3COO-, BzO-, CN-, and F-. The interactions were analyzed by spectrophotometric titrations and the stoichiometry of the interaction was assessed by the method of continuous variation. Compound 3b showed a remarkable sensitivity to CN- with a limit of detection of 0.35 µM. The interaction of compound 3b with CN- and F- was also analyzed by 1H NMR titrations showing that increasing concentration of anion induces a deprotonation of NH and OH groups.Thanks are due to Fundação para a Ciência e Tecnologia (FCT) and FEDER (European Fund for Regional Development)-COMPETE-QRENEU for financial support through the Chemistry Research Centre of the University of Minho (Ref. CQ/UM (UID/QUI/00686/2020)), and a PhD grant to R.P.C.L.S. (SFRH/BD/145639/2019). The NMR spectrometer Bruker Avance III 400 is part of the National NMR Network (PTNMR) and was financially partially supported by Infrastructure Project No. 022161 (co-financed by FEDER through COMPETE 2020, POCI and PORL, and FCT through PIDDAC).MDPIUniversidade do MinhoSousa, Rui P. C. L.Costa, Susana P. G.Figueira, Rita B.Raposo, M. Manuela M.20222022-01-01T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/articleapplication/pdfhttps://hdl.handle.net/1822/80385engSousa, R.P.C.L.; Costa, S.P.G.; Figueira, R.B.; Raposo, M.M.M. New Dinitrophenyl Hydrazones as Colorimetric Probes for Anions. Chemosensors 2022, 10, 384. https://doi.org/10.3390/chemosensors101003842227-904010.3390/chemosensors10100384https://www.mdpi.com/2227-9040/10/10/384info: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:RCAAP2023-07-21T12:39:43Zoai:repositorium.sdum.uminho.pt:1822/80385Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-19T19:36:22.032352Repositório 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 New dinitrophenyl hydrazones as colorimetric probes for anions
title New dinitrophenyl hydrazones as colorimetric probes for anions
spellingShingle New dinitrophenyl hydrazones as colorimetric probes for anions
Sousa, Rui P. C. L.
synthesis
heterocycles
Colorimetric probe
anions
hydrazone
quinoline
colorimetric chemosensor
Ciências Naturais::Ciências Químicas
Science & Technology
Saúde de qualidade
title_short New dinitrophenyl hydrazones as colorimetric probes for anions
title_full New dinitrophenyl hydrazones as colorimetric probes for anions
title_fullStr New dinitrophenyl hydrazones as colorimetric probes for anions
title_full_unstemmed New dinitrophenyl hydrazones as colorimetric probes for anions
title_sort New dinitrophenyl hydrazones as colorimetric probes for anions
author Sousa, Rui P. C. L.
author_facet Sousa, Rui P. C. L.
Costa, Susana P. G.
Figueira, Rita B.
Raposo, M. Manuela M.
author_role author
author2 Costa, Susana P. G.
Figueira, Rita B.
Raposo, M. Manuela M.
author2_role author
author
author
dc.contributor.none.fl_str_mv Universidade do Minho
dc.contributor.author.fl_str_mv Sousa, Rui P. C. L.
Costa, Susana P. G.
Figueira, Rita B.
Raposo, M. Manuela M.
dc.subject.por.fl_str_mv synthesis
heterocycles
Colorimetric probe
anions
hydrazone
quinoline
colorimetric chemosensor
Ciências Naturais::Ciências Químicas
Science & Technology
Saúde de qualidade
topic synthesis
heterocycles
Colorimetric probe
anions
hydrazone
quinoline
colorimetric chemosensor
Ciências Naturais::Ciências Químicas
Science & Technology
Saúde de qualidade
description Anion sensing is a dynamic research field due to biological and environmental importance of some organic or inorganic anions. Hydrazones show promising properties in the design of anion chemosensors due to the presence of proton donor and acceptor sites in their structure. In this work, two novel dinitrophenyl hydrazones, functionalized with a quinoline moiety were synthesized and characterized by spectroscopic and spectrometric techniques. The interaction between the new compounds 3a-b with different organic and inorganic anions was assessed. The two compounds showed a change of color from light yellow to magenta in the presence of H2PO4-, CH3COO-, BzO-, CN-, and F-. The interactions were analyzed by spectrophotometric titrations and the stoichiometry of the interaction was assessed by the method of continuous variation. Compound 3b showed a remarkable sensitivity to CN- with a limit of detection of 0.35 µM. The interaction of compound 3b with CN- and F- was also analyzed by 1H NMR titrations showing that increasing concentration of anion induces a deprotonation of NH and OH groups.
publishDate 2022
dc.date.none.fl_str_mv 2022
2022-01-01T00:00:00Z
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 https://hdl.handle.net/1822/80385
url https://hdl.handle.net/1822/80385
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv Sousa, R.P.C.L.; Costa, S.P.G.; Figueira, R.B.; Raposo, M.M.M. New Dinitrophenyl Hydrazones as Colorimetric Probes for Anions. Chemosensors 2022, 10, 384. https://doi.org/10.3390/chemosensors10100384
2227-9040
10.3390/chemosensors10100384
https://www.mdpi.com/2227-9040/10/10/384
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 MDPI
publisher.none.fl_str_mv MDPI
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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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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