Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence

Four new dyes that derive from borylated arylisoquinolines were prepared, containing a third aryl residue (naphthyl, 4-methoxynaphthyl, pyrenyl or anthryl) that is linked via an additional stereogenic axis. The triaryl cores were synthesized by Suzuki couplings and then transformed into boronic acid...

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Detalles Bibliográficos
Autores: Pais, Vânia F., Neumann, Tristan, Vayá, Ignacio, Jiménez, M. Consuelo, Ros, Abel, Pischel, Uwe
Tipo de recurso: artículo
Estado:Versión publicada
Fecha de publicación:2019
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/196778
Acceso en línea:http://hdl.handle.net/10261/196778
Access Level:acceso abierto
Palabra clave:Anions
Dyes
Fluorescence
Laser-flash photolysis
Orhanoboron
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repository_id_str
spelling Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescencePais, Vânia F.Neumann, TristanVayá, IgnacioJiménez, M. ConsueloRos, AbelPischel, UweAnionsDyesFluorescenceLaser-flash photolysisOrhanoboronFour new dyes that derive from borylated arylisoquinolines were prepared, containing a third aryl residue (naphthyl, 4-methoxynaphthyl, pyrenyl or anthryl) that is linked via an additional stereogenic axis. The triaryl cores were synthesized by Suzuki couplings and then transformed into boronic acid esters by employing an Ir(I)-catalyzed reaction. The chromophores show dual emission behavior, where the long-wavelength emission band can reach maxima close to 600 nm in polar solvents. The fluorescence quantum yields of the dyes are generally in the range of 0.2–0.4, reaching in some cases values as high as 0.5–0.6. Laserflash photolysis provided evidence for the existence of excited triplet states. The dyes form fluoroboronate complexes with fluoride anions, leading to the observation of the quenching of the long-wavelength emission band and ratiometric response by the build-up of a hypsochromically shifted emission signalPeer reviewedBeilstein InstitutMinisterio de Economía, Industria y Competitividad (España)Agencia Estatal de Investigación (España)Agencia Estatal de Investigación (España)Agencia Estatal de Investigación (España)Ministerio de Ciencia, Innovación y Universidades (España)Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]201920192019info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/196778reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#CTQ2017-89416-R/AEI/10.13039/501100011033CTQ2017-89832-P/AEI/10.13039/501100011033info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-89832-Pinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016- 78875-Pinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-89416-Rhttp://dx.doi.org/10.3762/bjoc.15.254Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1967782026-05-22T06:33:51Z
dc.title.none.fl_str_mv Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence
title Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence
spellingShingle Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence
Pais, Vânia F.
Anions
Dyes
Fluorescence
Laser-flash photolysis
Orhanoboron
title_short Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence
title_full Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence
title_fullStr Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence
title_full_unstemmed Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence
title_sort Arylisoquinoline-derived organoboron dyes with a triaryl skeleton show dual fluorescence
dc.creator.none.fl_str_mv Pais, Vânia F.
Neumann, Tristan
Vayá, Ignacio
Jiménez, M. Consuelo
Ros, Abel
Pischel, Uwe
author Pais, Vânia F.
author_facet Pais, Vânia F.
Neumann, Tristan
Vayá, Ignacio
Jiménez, M. Consuelo
Ros, Abel
Pischel, Uwe
author_role author
author2 Neumann, Tristan
Vayá, Ignacio
Jiménez, M. Consuelo
Ros, Abel
Pischel, Uwe
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía, Industria y Competitividad (España)
Agencia Estatal de Investigación (España)
Agencia Estatal de Investigación (España)
Agencia Estatal de Investigación (España)
Ministerio de Ciencia, Innovación y Universidades (España)
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Anions
Dyes
Fluorescence
Laser-flash photolysis
Orhanoboron
topic Anions
Dyes
Fluorescence
Laser-flash photolysis
Orhanoboron
description Four new dyes that derive from borylated arylisoquinolines were prepared, containing a third aryl residue (naphthyl, 4-methoxynaphthyl, pyrenyl or anthryl) that is linked via an additional stereogenic axis. The triaryl cores were synthesized by Suzuki couplings and then transformed into boronic acid esters by employing an Ir(I)-catalyzed reaction. The chromophores show dual emission behavior, where the long-wavelength emission band can reach maxima close to 600 nm in polar solvents. The fluorescence quantum yields of the dyes are generally in the range of 0.2–0.4, reaching in some cases values as high as 0.5–0.6. Laserflash photolysis provided evidence for the existence of excited triplet states. The dyes form fluoroboronate complexes with fluoride anions, leading to the observation of the quenching of the long-wavelength emission band and ratiometric response by the build-up of a hypsochromically shifted emission signal
publishDate 2019
dc.date.none.fl_str_mv 2019
2019
2019
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Publisher's version
info:eu-repo/semantics/publishedVersion
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/196778
url http://hdl.handle.net/10261/196778
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
CTQ2017-89416-R/AEI/10.13039/501100011033
CTQ2017-89832-P/AEI/10.13039/501100011033
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-89832-P
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016- 78875-P
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/CTQ2017-89416-R
http://dx.doi.org/10.3762/bjoc.15.254
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Beilstein Institut
publisher.none.fl_str_mv Beilstein Institut
dc.source.none.fl_str_mv reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC
instname:Consejo Superior de Investigaciones Científicas (CSIC)
instname_str Consejo Superior de Investigaciones Científicas (CSIC)
reponame_str DIGITAL.CSIC. Repositorio Institucional del CSIC
collection DIGITAL.CSIC. Repositorio Institucional del CSIC
repository.name.fl_str_mv
repository.mail.fl_str_mv
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score 15,812429

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