On-Surface Driven Formal Michael AdditionProduces m-PolyanilineOligomers on Pt (111)

[EN] On-surface synthesis is emerging as a highly rational bottom-up methodology for the synthesis of molecular structures that are unattainable or complex to obtain by wet chemistry. Here, oligomers of meta-polyaniline, a known ferromagnetic polymer, were synthesized from para-aminophenol building-...

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Autores: Ruiz del Árbol, Nerea, Sánchez-Sánchez, Carlos, Otero, Gonzalo, Martínez, José I., Andrés, Pedro L. de, Gómez-Herrero, Ana C., Merino, Pablo, Piantek, Marten, Serrate Donoso, David, Lacovig, Paolo, Lizzit, Silvano, Alemán, José, Ellis, Gary James, López, María Francisca, Martín-Gago, José A.
Tipo de recurso: artículo
Estado:Versión publicada
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:10261/227159
Acceso en línea:http://hdl.handle.net/10261/227159
Access Level:acceso abierto
Palabra clave:Coupling reactions
DFT
NC-AFM/STM
On-surface synthesis
Polyaniline
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spelling On-Surface Driven Formal Michael AdditionProduces m-PolyanilineOligomers on Pt (111)Ruiz del Árbol, NereaSánchez-Sánchez, CarlosOtero, GonzaloMartínez, José I.Andrés, Pedro L. deGómez-Herrero, Ana C.Merino, PabloPiantek, MartenSerrate Donoso, DavidLacovig, PaoloLizzit, SilvanoAlemán, JoséEllis, Gary JamesLópez, María FranciscaMartín-Gago, José A.Coupling reactionsDFTNC-AFM/STMOn-surface synthesisPolyaniline[EN] On-surface synthesis is emerging as a highly rational bottom-up methodology for the synthesis of molecular structures that are unattainable or complex to obtain by wet chemistry. Here, oligomers of meta-polyaniline, a known ferromagnetic polymer, were synthesized from para-aminophenol building-blocks via an unexpected and highly specific on-surface formal 1, 4 Michael-type addition at the meta position, driven by the reduction of the aminophenol molecule. We rationalize this dehydrogenation and coupling reaction mechanism with a combination of in situ scanning tunneling and non-contact atomic force microscopies, high-resolution synchrotron-based X-ray photoemission spectroscopy and first-principles calculations. This study demonstrates the capability of surfaces to selectively modify local molecular conditions to redirect well-established synthetic routes, such as Michael coupling, towards the rational synthesis of new covalent nanostructures.Spanish MINECO(MAT2017-85089-C2-1-R, RYC-2015–17730), European Research Council (ERC) under contract (ERC-2013-SYG-610256 NANOCOSMOS), Comunidad de Madrid via Programa de InvestigaciónTecnologías 2018 (FOTOART-CMS2018/NMT-4367), and the innovation program under grantagreements 785219 and 881603 (GrapheneCore2 and Gra-pheneCore3-Graphene-based disruptive technologies,re-spectively). CSS acknowledges MCIU for the “RamnyCajal” contract (RYC2018-024364-I). NRdA is grateful tothe Spanish MINECO for support from the FPI program(BES-2015–072642)Peer reviewedWiley-VCHMinisterio de Economía y Competitividad (España)European Research CouncilComunidad de MadridMinisterio de Ciencia, Innovación y Universidades (España)Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202120212020info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/227159reponame: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##PLACEHOLDER_PARENT_METADATA_VALUE##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/BES-2015–072642info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/MAT2017-85089-C2-1-Rinfo:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/RYC-2015–17730info:eu-repo/grantAgreement/EC/FP7/610256info:eu-repo/grantAgreement/EC/H2020/785219info:eu-repo/grantAgreement/EC/H2020/881603S2018/NMT-4367/FOTOARTinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/RYC2018-024364-Idoi.org/10.1002/anie.202009863doi.org/10.1002/ange.20200986323220Síinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/2271592026-05-22T06:33:51Z
dc.title.none.fl_str_mv On-Surface Driven Formal Michael AdditionProduces m-PolyanilineOligomers on Pt (111)
title On-Surface Driven Formal Michael AdditionProduces m-PolyanilineOligomers on Pt (111)
spellingShingle On-Surface Driven Formal Michael AdditionProduces m-PolyanilineOligomers on Pt (111)
Ruiz del Árbol, Nerea
Coupling reactions
DFT
NC-AFM/STM
On-surface synthesis
Polyaniline
title_short On-Surface Driven Formal Michael AdditionProduces m-PolyanilineOligomers on Pt (111)
title_full On-Surface Driven Formal Michael AdditionProduces m-PolyanilineOligomers on Pt (111)
title_fullStr On-Surface Driven Formal Michael AdditionProduces m-PolyanilineOligomers on Pt (111)
title_full_unstemmed On-Surface Driven Formal Michael AdditionProduces m-PolyanilineOligomers on Pt (111)
title_sort On-Surface Driven Formal Michael AdditionProduces m-PolyanilineOligomers on Pt (111)
dc.creator.none.fl_str_mv Ruiz del Árbol, Nerea
Sánchez-Sánchez, Carlos
Otero, Gonzalo
Martínez, José I.
Andrés, Pedro L. de
Gómez-Herrero, Ana C.
Merino, Pablo
Piantek, Marten
Serrate Donoso, David
Lacovig, Paolo
Lizzit, Silvano
Alemán, José
Ellis, Gary James
López, María Francisca
Martín-Gago, José A.
author Ruiz del Árbol, Nerea
author_facet Ruiz del Árbol, Nerea
Sánchez-Sánchez, Carlos
Otero, Gonzalo
Martínez, José I.
Andrés, Pedro L. de
Gómez-Herrero, Ana C.
Merino, Pablo
Piantek, Marten
Serrate Donoso, David
Lacovig, Paolo
Lizzit, Silvano
Alemán, José
Ellis, Gary James
López, María Francisca
Martín-Gago, José A.
author_role author
author2 Sánchez-Sánchez, Carlos
Otero, Gonzalo
Martínez, José I.
Andrés, Pedro L. de
Gómez-Herrero, Ana C.
Merino, Pablo
Piantek, Marten
Serrate Donoso, David
Lacovig, Paolo
Lizzit, Silvano
Alemán, José
Ellis, Gary James
López, María Francisca
Martín-Gago, José A.
author2_role author
author
author
author
author
author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv Ministerio de Economía y Competitividad (España)
European Research Council
Comunidad de Madrid
Ministerio de Ciencia, Innovación y Universidades (España)
Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]
dc.subject.none.fl_str_mv Coupling reactions
DFT
NC-AFM/STM
On-surface synthesis
Polyaniline
topic Coupling reactions
DFT
NC-AFM/STM
On-surface synthesis
Polyaniline
description [EN] On-surface synthesis is emerging as a highly rational bottom-up methodology for the synthesis of molecular structures that are unattainable or complex to obtain by wet chemistry. Here, oligomers of meta-polyaniline, a known ferromagnetic polymer, were synthesized from para-aminophenol building-blocks via an unexpected and highly specific on-surface formal 1, 4 Michael-type addition at the meta position, driven by the reduction of the aminophenol molecule. We rationalize this dehydrogenation and coupling reaction mechanism with a combination of in situ scanning tunneling and non-contact atomic force microscopies, high-resolution synchrotron-based X-ray photoemission spectroscopy and first-principles calculations. This study demonstrates the capability of surfaces to selectively modify local molecular conditions to redirect well-established synthetic routes, such as Michael coupling, towards the rational synthesis of new covalent nanostructures.
publishDate 2020
dc.date.none.fl_str_mv 2020
2021
2021
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/10261/227159
url http://hdl.handle.net/10261/227159
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv #PLACEHOLDER_PARENT_METADATA_VALUE#
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#PLACEHOLDER_PARENT_METADATA_VALUE#
#PLACEHOLDER_PARENT_METADATA_VALUE#
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#PLACEHOLDER_PARENT_METADATA_VALUE#
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/BES-2015–072642
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/MAT2017-85089-C2-1-R
info:eu-repo/grantAgreement/MINECO/Plan Estatal de Investigación Científica y Técnica y de Innovación 2013-2016/RYC-2015–17730
info:eu-repo/grantAgreement/EC/FP7/610256
info:eu-repo/grantAgreement/EC/H2020/785219
info:eu-repo/grantAgreement/EC/H2020/881603
S2018/NMT-4367/FOTOART
info:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/RYC2018-024364-I
doi.org/10.1002/anie.202009863
doi.org/10.1002/ange.20200986323220
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
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