Naphthalimide-Dyes Bearing Phosphine and Phosphorylamide Moieties

Detalhes bibliográficos
Autor(a) principal: Tosolini, Massimo
Data de Publicação: 2023
Outros Autores: Alberoni, Chiara, Outis, Mani, Parola, António Jorge, Milani, Barbara, Tecilla, Paolo, Avó, João
Tipo de documento: Artigo
Idioma: eng
Título da fonte: Repositório Científico de Acesso Aberto de Portugal (Repositórios Cientìficos)
Texto Completo: http://hdl.handle.net/10362/164072
Resumo: This work was supported by MUR-PRIN BacHounds project N° 2017E44 A9P_005. Publisher Copyright: © 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
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spelling Naphthalimide-Dyes Bearing Phosphine and Phosphorylamide MoietiesSynthesis and Optical PropertiesnaphthalimideNMR investigationoptical propertiesPd complexesphosphorylamidesCatalysisChemistry(all)Organic ChemistryThis work was supported by MUR-PRIN BacHounds project N° 2017E44 A9P_005. Publisher Copyright: © 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.1,8-Naphthalimides (NIs) represent a class of organic dyes with interesting optical properties that has been extensively explored in the last decades in lighting devices, chemosensors, optical probes or medicinal chemistry. However, despite their remarkable potential, reports on organometallic dyes bearing NIs are scarce and virtually inexistent regarding palladium(II) complexes. Herein, we report the synthesis of NIs bearing phosphine and amine chelating moieties and the characterization of their optical properties both as single molecules and when complexed on Pd(II) ions. It is shown that the introduction of phosphine moieties in the naphthalimide core results in a marked increase in non-radiative processes, leading to a significant reduction of the emission efficiency and lifetime of these dyes, compared to amine-bearing counterparts. The complexation to Pd(II) sequesters the electronic contribution of chelating moieties, with complexes assuming an optical behavior similar to that of unsubstituted 1,8-naphthalimide. The complexation significantly increases the acidity of chelating secondary amines, giving rise to an unexpected intramolecular reaction that results in the formation of a novel 1,8-naphthalimide dye bearing a cyclic phosphorylamide moiety. The new dye exhibits good emission quantum yield, long fluorescence lifetime and sensitivity to basic media, evidencing potential for application in optical imaging and sensing scenarios.LAQV@REQUIMTEDQ - Departamento de QuímicaRUNTosolini, MassimoAlberoni, ChiaraOutis, ManiParola, António JorgeMilani, BarbaraTecilla, PaoloAvó, João2024-02-23T23:45:46Z2023-09-152023-09-15T00:00:00Zinfo:eu-repo/semantics/publishedVersioninfo:eu-repo/semantics/article13application/pdfhttp://hdl.handle.net/10362/164072eng0947-6539PURE: 83886131https://doi.org/10.1002/chem.202301597info: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:RCAAP2024-03-11T05:50:39Zoai:run.unl.pt:10362/164072Portal AgregadorONGhttps://www.rcaap.pt/oai/openaireopendoar:71602024-03-20T04:00:01.853761Repositório 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 Naphthalimide-Dyes Bearing Phosphine and Phosphorylamide Moieties
Synthesis and Optical Properties
title Naphthalimide-Dyes Bearing Phosphine and Phosphorylamide Moieties
spellingShingle Naphthalimide-Dyes Bearing Phosphine and Phosphorylamide Moieties
Tosolini, Massimo
naphthalimide
NMR investigation
optical properties
Pd complexes
phosphorylamides
Catalysis
Chemistry(all)
Organic Chemistry
title_short Naphthalimide-Dyes Bearing Phosphine and Phosphorylamide Moieties
title_full Naphthalimide-Dyes Bearing Phosphine and Phosphorylamide Moieties
title_fullStr Naphthalimide-Dyes Bearing Phosphine and Phosphorylamide Moieties
title_full_unstemmed Naphthalimide-Dyes Bearing Phosphine and Phosphorylamide Moieties
title_sort Naphthalimide-Dyes Bearing Phosphine and Phosphorylamide Moieties
author Tosolini, Massimo
author_facet Tosolini, Massimo
Alberoni, Chiara
Outis, Mani
Parola, António Jorge
Milani, Barbara
Tecilla, Paolo
Avó, João
author_role author
author2 Alberoni, Chiara
Outis, Mani
Parola, António Jorge
Milani, Barbara
Tecilla, Paolo
Avó, João
author2_role author
author
author
author
author
author
dc.contributor.none.fl_str_mv LAQV@REQUIMTE
DQ - Departamento de Química
RUN
dc.contributor.author.fl_str_mv Tosolini, Massimo
Alberoni, Chiara
Outis, Mani
Parola, António Jorge
Milani, Barbara
Tecilla, Paolo
Avó, João
dc.subject.por.fl_str_mv naphthalimide
NMR investigation
optical properties
Pd complexes
phosphorylamides
Catalysis
Chemistry(all)
Organic Chemistry
topic naphthalimide
NMR investigation
optical properties
Pd complexes
phosphorylamides
Catalysis
Chemistry(all)
Organic Chemistry
description This work was supported by MUR-PRIN BacHounds project N° 2017E44 A9P_005. Publisher Copyright: © 2023 The Authors. Chemistry - A European Journal published by Wiley-VCH GmbH.
publishDate 2023
dc.date.none.fl_str_mv 2023-09-15
2023-09-15T00:00:00Z
2024-02-23T23:45:46Z
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/10362/164072
url http://hdl.handle.net/10362/164072
dc.language.iso.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv 0947-6539
PURE: 83886131
https://doi.org/10.1002/chem.202301597
dc.rights.driver.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.format.none.fl_str_mv 13
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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)
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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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