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Naphthalimide-Dyes Bearing Phosphine and Phosphorylamide Moieties

2023-09-15Artigo científico Acesso aberto
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dc.contributor.authorTosolini, Massimo
dc.contributor.authorAlberoni, Chiara
dc.contributor.authorOutis, Mani
dc.contributor.authorParola, António Jorge
dc.contributor.authorMilani, Barbara
dc.contributor.authorTecilla, Paolo
dc.contributor.authorAvó, João
dc.contributor.institutionLAQV@REQUIMTE
dc.contributor.institutionDQ - Departamento de Química
dc.contributor.pblWiley
dc.date.accessioned2024-02-23T23:45:46Z
dc.date.available2024-02-23T23:45:46Z
dc.date.issued2023-09-15
dc.descriptionThis 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.
dc.description.abstract1,8-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.en
dc.description.versionpublishersversion
dc.description.versionpublished
dc.format.extent13
dc.format.extent6432717
dc.identifier.doi10.1002/chem.202301597
dc.identifier.issn0947-6539
dc.identifier.otherPURE: 83886131
dc.identifier.otherPURE UUID: e35e9de3-5113-4caa-af28-94d647a2fb09
dc.identifier.otherScopus: 85166942770
dc.identifier.otherWOS: 001044600700001
dc.identifier.otherPubMed: 37377174
dc.identifier.otherORCID: /0000-0002-1333-9076/work/153922746
dc.identifier.urihttp://hdl.handle.net/10362/164072
dc.identifier.urlhttps://www.scopus.com/pages/publications/85166942770
dc.language.isoeng
dc.peerreviewedyes
dc.relationFunding Information: info:eu-repo/grantAgreement/FCT/OE/SFRH%2FBPD%2F120599%2F2016/PT
dc.relationinfo:eu-repo/grantAgreement/FCT/CEEC IND5ed/2022.01003.CEECIND%2FCP1725%2FCT0005/PT
dc.relationPhotonic Materials with Circularly Polarized Luminescence for Anti-Counterfeiting and Security Elements
dc.relationDelayed Fluorescence Nanomaterials for Imaging and Sensing
dc.relationAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
dc.relationAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
dc.relationinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F50006%2F2020/PT
dc.subjectnaphthalimide
dc.subjectNMR investigation
dc.subjectoptical properties
dc.subjectPd complexes
dc.subjectphosphorylamides
dc.subjectCatalysis
dc.subjectGeneral Chemistry
dc.subjectOrganic Chemistry
dc.titleNaphthalimide-Dyes Bearing Phosphine and Phosphorylamide Moietiesen
dc.title.subtitleSynthesis and Optical Propertiesen
dc.typejournal article
degois.publication.issue52
degois.publication.titleChemistry - A European Journal
degois.publication.volume29
dspace.entity.typePublication
oaire.awardNumber2022.01003.CEECIND/CP1725/CT0005
oaire.awardNumberPTDC/QUI-QFI/32007/2017
oaire.awardNumberUIDB/50006/2020
oaire.awardNumberUIDP/50006/2020
oaire.awardTitlePhotonic Materials with Circularly Polarized Luminescence for Anti-Counterfeiting and Security Elements
oaire.awardTitleDelayed Fluorescence Nanomaterials for Imaging and Sensing
oaire.awardTitleAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
oaire.awardTitleAssociated Laboratory for Green Chemistry - Clean Technologies and Processes
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/CEEC IND5ed/2022.01003.CEECIND%2FCP1725%2FCT0005/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/Concurso para Financiamento de Projetos de Investigação Científica e Desenvolvimento Tecnológico em Todos os Domínios Científicos - 2017/PTDC%2FQUI-QFI%2F32007%2F2017/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDB%2F50006%2F2020/PT
oaire.awardURIinfo:eu-repo/grantAgreement/FCT/6817 - DCRRNI ID/UIDP%2F50006%2F2020/PT
oaire.fundingStreamCEEC IND5ed
oaire.fundingStreamConcurso para Financiamento de Projetos de Investigação Científica e Desenvolvimento Tecnológico em Todos os Domínios Científicos - 2017
oaire.fundingStream6817 - DCRRNI ID
oaire.fundingStream6817 - DCRRNI ID
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.identifierhttp://doi.org/10.13039/501100001871
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
project.funder.nameFundação para a Ciência e a Tecnologia
rcaap.rightsopenAccess
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