Copper(II) complexes of bis(aryl-imino)acenaphthene ligands: synthesis, structure, DFT studies and evaluation in reverse ATRP of styrene

Autores
Fliedel, Christophe; Rosa, Vitor; Santos, Carla I. M.; González, Pablo Javier; Almeida, Rui M.; Gomes, Clara S. B.; Gomes, Pedro T.; Lemos, M. Amélia N. D. A.; Aullón, Gabriel; Welter, Richard; Avilés, Teresa
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Two new Ar-BIAN Cu(II) complexes (where Ar-BIAN = bis(aryl-imino)acenaphthene) of formulations [CuCl2(Mes-BIAN)] (1) (Mes = 2,4,6-Me3C6H2) and [CuCl2(Dipp-BIAN)] (2) (Dipp = 2,6-iPr2C6H3) were synthesised by direct reaction of CuCl2 suspended in dichloromethane with the respective ligands Mes-BIAN (L1) and Dipp-BIAN (L2), dissolved in dichloromethane, under an argon atmosphere. Attempts to obtain these compounds by solubilising CuCl2 in methanol and adding a dichloromethane solution of the corresponding ligand, under aerobic conditions, gave also compound 1, but, in the case of L2, the Cu(I) dimer [CuCl(Dipp-BIAN)]2 (3) was obtained instead of compound 2. The compounds were fully characterised by elemental analyses, MALDI-TOF mass spectrometry, FT-IR, 1H NMR and EPR spectroscopic techniques. The solid-state molecular structures of compounds 1?3 were determined by single crystal X-ray diffraction, showing the expected chelation of the Ar-BIAN ligands and two chloride ligands completing the coordination sphere of the Cu(II) centre. In the case of the complex 1, an intermediate coordination geometry around the Cu(II) centre, between square planar and tetrahedral, was revealed, while the complex 2 showed an almost square planar geometry. The structural differences and evaluation of energetic changes were rationalised by DFT calculations. Analysis of the electrochemical behaviour of complexes 1?3 was performed by cyclic voltammetry and the experimental redox potentials for Cu(II)/Cu(I) pairs have been compared with theoretical values calculated by DFT in the gas phase and in dichloromethane and methanol solutions. The complex 1 exhibited good activity in the reverse atom transfer radical polymerisation (ATRP) of styrene.
Fil: Fliedel, Christophe. Universidade Nova de Lisboa. Faculdade de Ciências e Tecnologia. Departamento de Química; Portugal
Fil: Rosa, Vitor. Universidade Nova de Lisboa. Faculdade de Ciências e Tecnologia. Departamento de Química; Portugal
Fil: Santos, Carla I. M.. Universidade Nova de Lisboa. Faculdade de Ciências e Tecnologia. Departamento de Química; Portugal
Fil: González, Pablo Javier. Universidade Nova de Lisboa. Faculdade de Ciências e Tecnologia. Departamento de Química; Portugal. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Almeida, Rui M.. Universidade Nova de Lisboa. Faculdade de Ciências e Tecnologia. Departamento de Química; Portugal
Fil: Gomes, Clara S. B.. Universidade de Lisboa. Instituto Superior Técnico. Departamento de Engenharia Química. Centro de Química Estrutural; Portugal
Fil: Gomes, Pedro T.. Universidade de Lisboa. Instituto Superior Técnico. Departamento de Engenharia Química. Centro de Química Estrutural; Portugal
Fil: Lemos, M. Amélia N. D. A.. Universidade de Lisboa. Instituto Superior Técnico. IBB/CERENA ; Portugal
Fil: Aullón, Gabriel. Departament de Química Inorgànica and Institut de Química Teòrica i Computacional de Barcelona; España
Fil: Welter, Richard. University of Strasbourg. Institute of Plant Molecular Biology; Francia
Fil: Avilés, Teresa. Universidade Nova de Lisboa. Faculdade de Ciências e Tecnologia. Departamento de Química; Portugal
Materia
Copper
Epr
Nmr
Dft
Electrochemistry
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/16311
Acceder
id CONICETDig_24acb0920967d820a19bc7770bbb35c7
oai_identifier_str oai:ri.conicet.gov.ar:11336/16311
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Copper(II) complexes of bis(aryl-imino)acenaphthene ligands: synthesis, structure, DFT studies and evaluation in reverse ATRP of styreneFliedel, ChristopheRosa, VitorSantos, Carla I. M.González, Pablo JavierAlmeida, Rui M.Gomes, Clara S. B.Gomes, Pedro T.Lemos, M. Amélia N. D. A.Aullón, GabrielWelter, RichardAvilés, TeresaCopperEprNmrDftElectrochemistryhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Two new Ar-BIAN Cu(II) complexes (where Ar-BIAN = bis(aryl-imino)acenaphthene) of formulations [CuCl2(Mes-BIAN)] (1) (Mes = 2,4,6-Me3C6H2) and [CuCl2(Dipp-BIAN)] (2) (Dipp = 2,6-iPr2C6H3) were synthesised by direct reaction of CuCl2 suspended in dichloromethane with the respective ligands Mes-BIAN (L1) and Dipp-BIAN (L2), dissolved in dichloromethane, under an argon atmosphere. Attempts to obtain these compounds by solubilising CuCl2 in methanol and adding a dichloromethane solution of the corresponding ligand, under aerobic conditions, gave also compound 1, but, in the case of L2, the Cu(I) dimer [CuCl(Dipp-BIAN)]2 (3) was obtained instead of compound 2. The compounds were fully characterised by elemental analyses, MALDI-TOF mass spectrometry, FT-IR, 1H NMR and EPR spectroscopic techniques. The solid-state molecular structures of compounds 1?3 were determined by single crystal X-ray diffraction, showing the expected chelation of the Ar-BIAN ligands and two chloride ligands completing the coordination sphere of the Cu(II) centre. In the case of the complex 1, an intermediate coordination geometry around the Cu(II) centre, between square planar and tetrahedral, was revealed, while the complex 2 showed an almost square planar geometry. The structural differences and evaluation of energetic changes were rationalised by DFT calculations. Analysis of the electrochemical behaviour of complexes 1?3 was performed by cyclic voltammetry and the experimental redox potentials for Cu(II)/Cu(I) pairs have been compared with theoretical values calculated by DFT in the gas phase and in dichloromethane and methanol solutions. The complex 1 exhibited good activity in the reverse atom transfer radical polymerisation (ATRP) of styrene.Fil: Fliedel, Christophe. Universidade Nova de Lisboa. Faculdade de Ciências e Tecnologia. Departamento de Química; PortugalFil: Rosa, Vitor. Universidade Nova de Lisboa. Faculdade de Ciências e Tecnologia. Departamento de Química; PortugalFil: Santos, Carla I. M.. Universidade Nova de Lisboa. Faculdade de Ciências e Tecnologia. Departamento de Química; PortugalFil: González, Pablo Javier. Universidade Nova de Lisboa. Faculdade de Ciências e Tecnologia. Departamento de Química; Portugal. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Almeida, Rui M.. Universidade Nova de Lisboa. Faculdade de Ciências e Tecnologia. Departamento de Química; PortugalFil: Gomes, Clara S. B.. Universidade de Lisboa. Instituto Superior Técnico. Departamento de Engenharia Química. Centro de Química Estrutural; PortugalFil: Gomes, Pedro T.. Universidade de Lisboa. Instituto Superior Técnico. Departamento de Engenharia Química. Centro de Química Estrutural; PortugalFil: Lemos, M. Amélia N. D. A.. Universidade de Lisboa. Instituto Superior Técnico. IBB/CERENA ; PortugalFil: Aullón, Gabriel. Departament de Química Inorgànica and Institut de Química Teòrica i Computacional de Barcelona; EspañaFil: Welter, Richard. University of Strasbourg. Institute of Plant Molecular Biology; FranciaFil: Avilés, Teresa. Universidade Nova de Lisboa. Faculdade de Ciências e Tecnologia. Departamento de Química; PortugalRoyal Society Of Chemistry2014-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/16311Fliedel, Christophe; Rosa, Vitor; Santos, Carla I. M.; González, Pablo Javier; Almeida, Rui M.; et al.; Copper(II) complexes of bis(aryl-imino)acenaphthene ligands: synthesis, structure, DFT studies and evaluation in reverse ATRP of styrene; Royal Society Of Chemistry; Dalton Transactions; 43; 34; 6-2014; 13041-130541477-9226enginfo:eu-repo/semantics/altIdentifier/doi/10.1039/c4dt01069hinfo:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2014/DT/C4DT01069H#!divAbstractinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:51:22Zoai:ri.conicet.gov.ar:11336/16311instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-09-29 09:51:22.333CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Copper(II) complexes of bis(aryl-imino)acenaphthene ligands: synthesis, structure, DFT studies and evaluation in reverse ATRP of styrene
title Copper(II) complexes of bis(aryl-imino)acenaphthene ligands: synthesis, structure, DFT studies and evaluation in reverse ATRP of styrene
spellingShingle Copper(II) complexes of bis(aryl-imino)acenaphthene ligands: synthesis, structure, DFT studies and evaluation in reverse ATRP of styrene
Fliedel, Christophe
Copper
Epr
Nmr
Dft
Electrochemistry
title_short Copper(II) complexes of bis(aryl-imino)acenaphthene ligands: synthesis, structure, DFT studies and evaluation in reverse ATRP of styrene
title_full Copper(II) complexes of bis(aryl-imino)acenaphthene ligands: synthesis, structure, DFT studies and evaluation in reverse ATRP of styrene
title_fullStr Copper(II) complexes of bis(aryl-imino)acenaphthene ligands: synthesis, structure, DFT studies and evaluation in reverse ATRP of styrene
title_full_unstemmed Copper(II) complexes of bis(aryl-imino)acenaphthene ligands: synthesis, structure, DFT studies and evaluation in reverse ATRP of styrene
title_sort Copper(II) complexes of bis(aryl-imino)acenaphthene ligands: synthesis, structure, DFT studies and evaluation in reverse ATRP of styrene
dc.creator.none.fl_str_mv Fliedel, Christophe
Rosa, Vitor
Santos, Carla I. M.
González, Pablo Javier
Almeida, Rui M.
Gomes, Clara S. B.
Gomes, Pedro T.
Lemos, M. Amélia N. D. A.
Aullón, Gabriel
Welter, Richard
Avilés, Teresa
author Fliedel, Christophe
author_facet Fliedel, Christophe
Rosa, Vitor
Santos, Carla I. M.
González, Pablo Javier
Almeida, Rui M.
Gomes, Clara S. B.
Gomes, Pedro T.
Lemos, M. Amélia N. D. A.
Aullón, Gabriel
Welter, Richard
Avilés, Teresa
author_role author
author2 Rosa, Vitor
Santos, Carla I. M.
González, Pablo Javier
Almeida, Rui M.
Gomes, Clara S. B.
Gomes, Pedro T.
Lemos, M. Amélia N. D. A.
Aullón, Gabriel
Welter, Richard
Avilés, Teresa
author2_role author
author
author
author
author
author
author
author
author
author
dc.subject.none.fl_str_mv Copper
Epr
Nmr
Dft
Electrochemistry
topic Copper
Epr
Nmr
Dft
Electrochemistry
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Two new Ar-BIAN Cu(II) complexes (where Ar-BIAN = bis(aryl-imino)acenaphthene) of formulations [CuCl2(Mes-BIAN)] (1) (Mes = 2,4,6-Me3C6H2) and [CuCl2(Dipp-BIAN)] (2) (Dipp = 2,6-iPr2C6H3) were synthesised by direct reaction of CuCl2 suspended in dichloromethane with the respective ligands Mes-BIAN (L1) and Dipp-BIAN (L2), dissolved in dichloromethane, under an argon atmosphere. Attempts to obtain these compounds by solubilising CuCl2 in methanol and adding a dichloromethane solution of the corresponding ligand, under aerobic conditions, gave also compound 1, but, in the case of L2, the Cu(I) dimer [CuCl(Dipp-BIAN)]2 (3) was obtained instead of compound 2. The compounds were fully characterised by elemental analyses, MALDI-TOF mass spectrometry, FT-IR, 1H NMR and EPR spectroscopic techniques. The solid-state molecular structures of compounds 1?3 were determined by single crystal X-ray diffraction, showing the expected chelation of the Ar-BIAN ligands and two chloride ligands completing the coordination sphere of the Cu(II) centre. In the case of the complex 1, an intermediate coordination geometry around the Cu(II) centre, between square planar and tetrahedral, was revealed, while the complex 2 showed an almost square planar geometry. The structural differences and evaluation of energetic changes were rationalised by DFT calculations. Analysis of the electrochemical behaviour of complexes 1?3 was performed by cyclic voltammetry and the experimental redox potentials for Cu(II)/Cu(I) pairs have been compared with theoretical values calculated by DFT in the gas phase and in dichloromethane and methanol solutions. The complex 1 exhibited good activity in the reverse atom transfer radical polymerisation (ATRP) of styrene.
Fil: Fliedel, Christophe. Universidade Nova de Lisboa. Faculdade de Ciências e Tecnologia. Departamento de Química; Portugal
Fil: Rosa, Vitor. Universidade Nova de Lisboa. Faculdade de Ciências e Tecnologia. Departamento de Química; Portugal
Fil: Santos, Carla I. M.. Universidade Nova de Lisboa. Faculdade de Ciências e Tecnologia. Departamento de Química; Portugal
Fil: González, Pablo Javier. Universidade Nova de Lisboa. Faculdade de Ciências e Tecnologia. Departamento de Química; Portugal. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Almeida, Rui M.. Universidade Nova de Lisboa. Faculdade de Ciências e Tecnologia. Departamento de Química; Portugal
Fil: Gomes, Clara S. B.. Universidade de Lisboa. Instituto Superior Técnico. Departamento de Engenharia Química. Centro de Química Estrutural; Portugal
Fil: Gomes, Pedro T.. Universidade de Lisboa. Instituto Superior Técnico. Departamento de Engenharia Química. Centro de Química Estrutural; Portugal
Fil: Lemos, M. Amélia N. D. A.. Universidade de Lisboa. Instituto Superior Técnico. IBB/CERENA ; Portugal
Fil: Aullón, Gabriel. Departament de Química Inorgànica and Institut de Química Teòrica i Computacional de Barcelona; España
Fil: Welter, Richard. University of Strasbourg. Institute of Plant Molecular Biology; Francia
Fil: Avilés, Teresa. Universidade Nova de Lisboa. Faculdade de Ciências e Tecnologia. Departamento de Química; Portugal
description Two new Ar-BIAN Cu(II) complexes (where Ar-BIAN = bis(aryl-imino)acenaphthene) of formulations [CuCl2(Mes-BIAN)] (1) (Mes = 2,4,6-Me3C6H2) and [CuCl2(Dipp-BIAN)] (2) (Dipp = 2,6-iPr2C6H3) were synthesised by direct reaction of CuCl2 suspended in dichloromethane with the respective ligands Mes-BIAN (L1) and Dipp-BIAN (L2), dissolved in dichloromethane, under an argon atmosphere. Attempts to obtain these compounds by solubilising CuCl2 in methanol and adding a dichloromethane solution of the corresponding ligand, under aerobic conditions, gave also compound 1, but, in the case of L2, the Cu(I) dimer [CuCl(Dipp-BIAN)]2 (3) was obtained instead of compound 2. The compounds were fully characterised by elemental analyses, MALDI-TOF mass spectrometry, FT-IR, 1H NMR and EPR spectroscopic techniques. The solid-state molecular structures of compounds 1?3 were determined by single crystal X-ray diffraction, showing the expected chelation of the Ar-BIAN ligands and two chloride ligands completing the coordination sphere of the Cu(II) centre. In the case of the complex 1, an intermediate coordination geometry around the Cu(II) centre, between square planar and tetrahedral, was revealed, while the complex 2 showed an almost square planar geometry. The structural differences and evaluation of energetic changes were rationalised by DFT calculations. Analysis of the electrochemical behaviour of complexes 1?3 was performed by cyclic voltammetry and the experimental redox potentials for Cu(II)/Cu(I) pairs have been compared with theoretical values calculated by DFT in the gas phase and in dichloromethane and methanol solutions. The complex 1 exhibited good activity in the reverse atom transfer radical polymerisation (ATRP) of styrene.
publishDate 2014
dc.date.none.fl_str_mv 2014-06
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/16311
Fliedel, Christophe; Rosa, Vitor; Santos, Carla I. M.; González, Pablo Javier; Almeida, Rui M.; et al.; Copper(II) complexes of bis(aryl-imino)acenaphthene ligands: synthesis, structure, DFT studies and evaluation in reverse ATRP of styrene; Royal Society Of Chemistry; Dalton Transactions; 43; 34; 6-2014; 13041-13054
1477-9226
url http://hdl.handle.net/11336/16311
identifier_str_mv Fliedel, Christophe; Rosa, Vitor; Santos, Carla I. M.; González, Pablo Javier; Almeida, Rui M.; et al.; Copper(II) complexes of bis(aryl-imino)acenaphthene ligands: synthesis, structure, DFT studies and evaluation in reverse ATRP of styrene; Royal Society Of Chemistry; Dalton Transactions; 43; 34; 6-2014; 13041-13054
1477-9226
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1039/c4dt01069h
info:eu-repo/semantics/altIdentifier/url/http://pubs.rsc.org/en/Content/ArticleLanding/2014/DT/C4DT01069H#!divAbstract
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Royal Society Of Chemistry
publisher.none.fl_str_mv Royal Society Of Chemistry
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 13.070432

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