Chiral-at-Metal BODIPY-Based Iridium(III) Complexes: Synthesis and Luminescence Properties

The synthesis of enantiomerically pure Ir(III) complexes with one or two BODIPY moieties has been achieved through the enantioselective C–H insertion from homochiral triazolium salts, containing a sulfoxide functionality in their structures. These homochiral salts were prepared by the sequential Cu-...

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Autores: Avello, Marta G., Torre, María C. de la, Guerrero-Martínez, A., Sierra, M. A., Gornitzka, H., Hemmert, Catherine
Tipo de recurso: artículo
Fecha de publicación:2020
País:España
Institución:Consejo Superior de Investigaciones Científicas (CSIC)
Repositorio:DIGITAL.CSIC. Repositorio Institucional del CSIC
OAI Identifier:oai:digital.csic.es:10261/229017
Acceso en línea:http://hdl.handle.net/10261/229017
Access Level:acceso abierto
Palabra clave:Chirality
Iridium
BODIPYs
Luminescence
7 MIC-ligands
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spelling Chiral-at-Metal BODIPY-Based Iridium(III) Complexes: Synthesis and Luminescence PropertiesAvello, Marta G.Torre, María C. de laGuerrero-Martínez, A.Sierra, M. A.Gornitzka, H.Hemmert, CatherineChiralityIridiumBODIPYsLuminescence7 MIC-ligandsThe synthesis of enantiomerically pure Ir(III) complexes with one or two BODIPY moieties has been achieved through the enantioselective C–H insertion from homochiral triazolium salts, containing a sulfoxide functionality in their structures. These homochiral salts were prepared by the sequential Cu-catalyzed alkyne-azide cycloaddition (CuAAC) of an azide and one alkynyl sulfoxide, followed by a Suzuki coupling in the preformed triazole with a BODIPY containing aryl boronic acid, followed by methylation of the N3-triazole nitrogen. The configuration at the metal in these chiral complexes was established by using a combination of CD and X-ray diffraction techniques. The optical properties of these complexes were thoroughly studied using spectroscopic (absorption and fluorescence) and computational (TD-DFT and DFT) methods. The fluorescence of complexes with the BODIPY attached to the sulfoxide moiety (including the two BODIPYs-based complex) was quenched upon introduction of the Ir(III) fragment, most likely due to an a-PET mechanism. On the contrary, the fluorescence of Ir(III) complexes with the BODIPY attached to the triazolium ring remains unquenched.Support for this work under grants CTQ2016-77555-C2-1-R to M. A. S., CTQ2016-77555-C2-2-R to M. C. T. and CTQ2016-81797- REDC Programa Redes Consolider from the AEI (Spain) is gratefully acknowledged. M. A. S. thanks the Fundación Ramón Areces for a grant from the XVII Concurso Nacional de Ayudas a la Investigación en Ciencias de la Vida y de la Materia (CIVP18A3938). Dr. Marta García-Avello thanks the AEI for one FPI predoctoral grant.Wiley-VCHMinisterio de Economía y Competitividad (España)Fundación Ramón ArecesConsejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]2021202120202021info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501http://hdl.handle.net/10261/229017reponame: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/CTQ2016-77555-C2-1-Rinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-81797-REDChttp://dx.doi.org/10.1002/ejic.202000745Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2290172026-05-22T06:33:51Z
dc.title.none.fl_str_mv Chiral-at-Metal BODIPY-Based Iridium(III) Complexes: Synthesis and Luminescence Properties
title Chiral-at-Metal BODIPY-Based Iridium(III) Complexes: Synthesis and Luminescence Properties
spellingShingle Chiral-at-Metal BODIPY-Based Iridium(III) Complexes: Synthesis and Luminescence Properties
Avello, Marta G.
Chirality
Iridium
BODIPYs
Luminescence
7 MIC-ligands
title_short Chiral-at-Metal BODIPY-Based Iridium(III) Complexes: Synthesis and Luminescence Properties
title_full Chiral-at-Metal BODIPY-Based Iridium(III) Complexes: Synthesis and Luminescence Properties
title_fullStr Chiral-at-Metal BODIPY-Based Iridium(III) Complexes: Synthesis and Luminescence Properties
title_full_unstemmed Chiral-at-Metal BODIPY-Based Iridium(III) Complexes: Synthesis and Luminescence Properties
title_sort Chiral-at-Metal BODIPY-Based Iridium(III) Complexes: Synthesis and Luminescence Properties
dc.creator.none.fl_str_mv Avello, Marta G.
Torre, María C. de la
Guerrero-Martínez, A.
Sierra, M. A.
Gornitzka, H.
Hemmert, Catherine
author Avello, Marta G.
author_facet Avello, Marta G.
Torre, María C. de la
Guerrero-Martínez, A.
Sierra, M. A.
Gornitzka, H.
Hemmert, Catherine
author_role author
author2 Torre, María C. de la
Guerrero-Martínez, A.
Sierra, M. A.
Gornitzka, H.
Hemmert, Catherine
author2_role author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
Fundación Ramón Areces
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Chirality
Iridium
BODIPYs
Luminescence
7 MIC-ligands
topic Chirality
Iridium
BODIPYs
Luminescence
7 MIC-ligands
description The synthesis of enantiomerically pure Ir(III) complexes with one or two BODIPY moieties has been achieved through the enantioselective C–H insertion from homochiral triazolium salts, containing a sulfoxide functionality in their structures. These homochiral salts were prepared by the sequential Cu-catalyzed alkyne-azide cycloaddition (CuAAC) of an azide and one alkynyl sulfoxide, followed by a Suzuki coupling in the preformed triazole with a BODIPY containing aryl boronic acid, followed by methylation of the N3-triazole nitrogen. The configuration at the metal in these chiral complexes was established by using a combination of CD and X-ray diffraction techniques. The optical properties of these complexes were thoroughly studied using spectroscopic (absorption and fluorescence) and computational (TD-DFT and DFT) methods. The fluorescence of complexes with the BODIPY attached to the sulfoxide moiety (including the two BODIPYs-based complex) was quenched upon introduction of the Ir(III) fragment, most likely due to an a-PET mechanism. On the contrary, the fluorescence of Ir(III) complexes with the BODIPY attached to the triazolium ring remains unquenched.
publishDate 2020
dc.date.none.fl_str_mv 2020
2021
2021
2021
dc.type.none.fl_str_mv info:eu-repo/semantics/article
http://purl.org/coar/resource_type/c_6501
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10261/229017
url http://hdl.handle.net/10261/229017
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/CTQ2016-77555-C2-1-R
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/CTQ2016-81797-REDC
http://dx.doi.org/10.1002/ejic.202000745
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
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score 15,81155

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