η1-arene complexes as intermediates in the preparation of molecular phosphorescent iridium(III) complexes

Molecular phosphorescent heteroleptic bis-tridentate iridium(III) emitters have been prepared via η1-arene intermediates. In the presence of 4.0 mol of AgOTf, the complex [(IrCl{κ3-N,C,N-(pyC6HMe2py)})(μ-Cl)]2 (1; pyC6H2Me2py=1,3-di(2-pyridyl)-4,6-dimethylbenzene) reacted with 9-(6-phenylpyridin-2-y...

Descripción completa

Detalles Bibliográficos
Autores: Esteruelas, Miguel A., Gómez-Bautista, Daniel, López, Ana M., Oñate, Enrique, Tsai, Jui-Yi, Xia, Chuanjun
Tipo de recurso: artículo
Estado:Versión aceptada para publicación
Fecha de publicación:2017
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/157080
Acceso en línea:http://hdl.handle.net/10261/157080
Access Level:acceso abierto
Palabra clave:C−H activation
Heteroleptic complexes
Iridium
Luminescence
Tridentate ligands
Arene ligands
id ES_d3909dfd3ad96ff8f8d4375492794a55
oai_identifier_str oai:digital.csic.es:10261/157080
network_acronym_str ES
network_name_str España
repository_id_str
spelling η1-arene complexes as intermediates in the preparation of molecular phosphorescent iridium(III) complexesEsteruelas, Miguel A.Gómez-Bautista, DanielLópez, Ana M.Oñate, EnriqueTsai, Jui-YiXia, ChuanjunC−H activationHeteroleptic complexesIridiumLuminescenceTridentate ligandsArene ligandsMolecular phosphorescent heteroleptic bis-tridentate iridium(III) emitters have been prepared via η1-arene intermediates. In the presence of 4.0 mol of AgOTf, the complex [(IrCl{κ3-N,C,N-(pyC6HMe2py)})(μ-Cl)]2 (1; pyC6H2Me2py=1,3-di(2-pyridyl)-4,6-dimethylbenzene) reacted with 9-(6-phenylpyridin-2-yl)-9H-carbazole (PhpyCzH) and 2-phenoxy-6-phenylpyridine (PhpyOPh) to give [Ir{κ3-N,C,N-(pyC6HMe2py)}{κ3-C,N,C′-(C6H4pyCzH)}]OTf (2) and [Ir{κ3-N,C,N-(pyC6HMe2py)}{κ3-C,N,C′-(C6H4pyOPh)}]OTf (3). The X-ray diffraction structures of 2 and 3 reveal that the carbazolyl and phenoxy substituents of the C,N,C′ ligand coordinate to the metal center to form an η1-arene π bond. Treatment of 2 and 3 with KOtBu led to the deprotonation of the coordinated carbon atom of the η1-arene group to afford the molecular phosphorescent [5t+4t′] heteroleptic iridium(III) complexes [Ir{κ3-N,C,N-(pyC6HMe2py)}{κ3-C,N,C′-(C6H4pyCz)}] (4) and [Ir{κ3-N,C,N-(pyC6HMe2py)}{κ3-C,N,C′-(C6H4pyOC6H4)}] (5). These complexes are green emitters that display short lifetimes and high quantum yields of 0.73 (4) and 0.87 (5) in the solid state.Financial support from the Spanish Ministerio de Economía y Competitividad (MINECO) (Projects CTQ2014-52799-P, Red de Excelencia Consolider CTQ2016-81797-REDC), the Gobierno deAragón (E35), Fondo Europeo de Desarrollo Regional (FEDER), and the European Social Fund (FSE) is acknowledged.Peer reviewedWiley-VCHMinisterio de Economía y Competitividad (España)Gobierno de AragónEuropean CommissionConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]201720172017info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Postprintinfo:eu-repo/semantics/acceptedVersionhttp://hdl.handle.net/10261/157080reponame:DIGITAL.CSIC. Repositorio Institucional del CSICinstname:Consejo Superior de Investigaciones Científicas (CSIC)Inglés#PLACEHOLDER_PARENT_METADATA_VALUE##PLACEHOLDER_PARENT_METADATA_VALUE#info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-52799-Pinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-81797-REDChttps://doi.org/10.1002/chem.201703252Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/1570802026-05-22T06:33:51Z
dc.title.none.fl_str_mv η1-arene complexes as intermediates in the preparation of molecular phosphorescent iridium(III) complexes
title η1-arene complexes as intermediates in the preparation of molecular phosphorescent iridium(III) complexes
spellingShingle η1-arene complexes as intermediates in the preparation of molecular phosphorescent iridium(III) complexes
Esteruelas, Miguel A.
C−H activation
Heteroleptic complexes
Iridium
Luminescence
Tridentate ligands
Arene ligands
title_short η1-arene complexes as intermediates in the preparation of molecular phosphorescent iridium(III) complexes
title_full η1-arene complexes as intermediates in the preparation of molecular phosphorescent iridium(III) complexes
title_fullStr η1-arene complexes as intermediates in the preparation of molecular phosphorescent iridium(III) complexes
title_full_unstemmed η1-arene complexes as intermediates in the preparation of molecular phosphorescent iridium(III) complexes
title_sort η1-arene complexes as intermediates in the preparation of molecular phosphorescent iridium(III) complexes
dc.creator.none.fl_str_mv Esteruelas, Miguel A.
Gómez-Bautista, Daniel
López, Ana M.
Oñate, Enrique
Tsai, Jui-Yi
Xia, Chuanjun
author Esteruelas, Miguel A.
author_facet Esteruelas, Miguel A.
Gómez-Bautista, Daniel
López, Ana M.
Oñate, Enrique
Tsai, Jui-Yi
Xia, Chuanjun
author_role author
author2 Gómez-Bautista, Daniel
López, Ana M.
Oñate, Enrique
Tsai, Jui-Yi
Xia, Chuanjun
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
Gobierno de Aragón
European Commission
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv C−H activation
Heteroleptic complexes
Iridium
Luminescence
Tridentate ligands
Arene ligands
topic C−H activation
Heteroleptic complexes
Iridium
Luminescence
Tridentate ligands
Arene ligands
description Molecular phosphorescent heteroleptic bis-tridentate iridium(III) emitters have been prepared via η1-arene intermediates. In the presence of 4.0 mol of AgOTf, the complex [(IrCl{κ3-N,C,N-(pyC6HMe2py)})(μ-Cl)]2 (1; pyC6H2Me2py=1,3-di(2-pyridyl)-4,6-dimethylbenzene) reacted with 9-(6-phenylpyridin-2-yl)-9H-carbazole (PhpyCzH) and 2-phenoxy-6-phenylpyridine (PhpyOPh) to give [Ir{κ3-N,C,N-(pyC6HMe2py)}{κ3-C,N,C′-(C6H4pyCzH)}]OTf (2) and [Ir{κ3-N,C,N-(pyC6HMe2py)}{κ3-C,N,C′-(C6H4pyOPh)}]OTf (3). The X-ray diffraction structures of 2 and 3 reveal that the carbazolyl and phenoxy substituents of the C,N,C′ ligand coordinate to the metal center to form an η1-arene π bond. Treatment of 2 and 3 with KOtBu led to the deprotonation of the coordinated carbon atom of the η1-arene group to afford the molecular phosphorescent [5t+4t′] heteroleptic iridium(III) complexes [Ir{κ3-N,C,N-(pyC6HMe2py)}{κ3-C,N,C′-(C6H4pyCz)}] (4) and [Ir{κ3-N,C,N-(pyC6HMe2py)}{κ3-C,N,C′-(C6H4pyOC6H4)}] (5). These complexes are green emitters that display short lifetimes and high quantum yields of 0.73 (4) and 0.87 (5) in the solid state.
publishDate 2017
dc.date.none.fl_str_mv 2017
2017
2017
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
Postprint
info:eu-repo/semantics/acceptedVersion
format article
status_str acceptedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/157080
url http://hdl.handle.net/10261/157080
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#
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2014-52799-P
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-81797-REDC
https://doi.org/10.1002/chem.201703252
Sí
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
eu_rights_str_mv openAccess
dc.publisher.none.fl_str_mv Wiley-VCH
publisher.none.fl_str_mv Wiley-VCH
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
_version_ 1869420470445539328
score 15,81155

Similares en LA Referencia