On-Surface Stepwise Double Dehydrogenation for the Formation of a para-Quinodimethane-Containing Undecacene Isomer

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dc.contributor.affiliationUniversidade de Santiago de Compostela. Centro de Investigación en Química Biolóxica e Materiais Moleculares (CiQUS)
dc.contributor.affiliationUniversidade de Santiago de Compostela. Departamento de Química Orgánica
dc.contributor.authorSarkar, Suchetana
dc.contributor.authorÁlvarez, Berta
dc.contributor.authorHo Au-Yeung, Kwan
dc.contributor.authorCobas Martínez, Agustín
dc.contributor.authorRobles, Roberto
dc.contributor.authorLorente, Nicolás
dc.contributor.authorPeña Gil, Diego
dc.contributor.authorPérez Meirás, María Dolores
dc.contributor.authorMoresco, Francesca
dc.date.accessioned2024-11-12T09:25:44Z
dc.date.available2024-11-12T09:25:44Z
dc.date.issued2024-07-20
dc.description.abstractThe on-surface synthesis of an isomer of undecacene, bearing two four-membered rings and two para-quinodimethane moieties, starting from a tetramethyl-substituted diepoxy precursor, is presented. The transformation implies a thermal double deoxygenation followed by a stepwise double dehydrogenation reaction on the Au(111) surface, locally induced by inelastic tunneling electrons. This results in the transformation of para-dimethylbenzene moieties into non-aromatic para-quinodimethanes. The structures and electronic properties of the intermediate and final products are investigated at the single molecule level with high spatial resolution, using both scanning tunneling microscopy/spectroscopy and non-contact atomic force microscopy. The experimental results are supported by density functional theory calculations.
dc.description.peerreviewedSI
dc.description.sponsorshipThis work was funded by the DFG Project 432345501, the European Innovation Council (EIC) under the project ESiM (grant agreement No 101046364), grants PD2019–110037GB−I00, PID2021–127917NB−I00, PID2022–139933NB−I00 and PID2022–140845OB−C62 funded by MICIU/AEI/ 10.13039/501100011033, QUAN-000021–01 funded by the Gipuzkoa Provincial Council and IT-1527–22 funded by the Basque Government the European Union Horizon 2020 through FET-Open Project SPRING (Grant No. 863098) and ERC Synergy Grant MolDAM (951519), the Xunta de Galicia (Centro singular de investigación de Galicia accreditation 2019–2022, ED431G 2019/03 and Oportunius Program) and the European Union (European Regional Development Fund-ERDF). Support from German Research Foundation (DFG) by the Collaborative Research Centre (CRC) 1415 is also gratefully acknowledged. We thank Alexander Tahn from the cfaed Dresden Center for Nanoanalysis (DCN), for FIB operations on the AFM tip and its SEM images. The authors thank the Centro de Supercomputación de Galicia (CESGA) for generous allocation of computer time.
dc.identifier.citationS. Sarkar, B. Álvarez, K. Ho Au-Yeung, A. Cobas, R. Robles, N. Lorente, D. Peña, D. Pérez, F. Moresco, Chem. Eur. J. 2024, 30, e202402297. https://doi.org/10.1002/chem.202402297
dc.identifier.doi10.1002/chem.202402297
dc.identifier.essn1521-3765
dc.identifier.urihttps://hdl.handle.net/10347/37673
dc.issue.number55
dc.journal.titleChemistry - A European Journal
dc.language.isoeng
dc.publisherWiley
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2017-2020/PID2019-110037GB-I00/ES/LEGO MOLECULAR BASADO EN ARINOS: APLICACION A LA SINTESIS DE HIDROCARBUROS POLICICLICOS CONJUGADOS Y MATERIALES π-FUNCIONALES/
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2021-127917NB-I00/ES/MOLECULAS COMO IMPUREZAS MAGNETICAS PARA TECNOLOGIAS CUANTICAS
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2022-139933NB-I00/ES/ARINOS Y CATALISIS METALICA: ESTRATEGIAS Y METODOS INNOVADORES PARA LA SINTESIS DE NANOESTRUCTURAS DE CARBONO NO CONVENCIONALES
dc.relation.projectIDinfo:eu-repo/grantAgreement/AEI/Plan Estatal de Investigación Científica y Técnica y de Innovación 2021-2023/PID2022-140845OB-I00/ES/SINTESIS EN SUPERFICIE DE ARQUITECTURAS MOLECULARES CON FUNCIONALIDAD OPTICA Y MAGNETICA
dc.relation.projectIDinfo:eu-repo/grantAgreement/EC/H2020/863098/EU
dc.relation.projectIDinfo:eu-repo/grantAgreement/EC/H2020/951519/EU
dc.relation.publisherversionhttps://doi.org/10.1002/chem.202402297
dc.rights© 2024 The Author(s). Chemistry - A European Journal published by Wiley-VCH GmbH
dc.rights.accessRightsopen access
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/
dc.subjectOn-Surface Synthesis
dc.subjectUndecacene isomer
dc.subjectPara-quinodimethane moieties
dc.subject.classificationInvestigación
dc.titleOn-Surface Stepwise Double Dehydrogenation for the Formation of a para-Quinodimethane-Containing Undecacene Isomer
dc.typejournal article
dc.type.hasVersionVoR
dc.volume.number30
dspace.entity.typePublication
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relation.isAuthorOfPublication.latestForDiscovery0e2473e3-afc3-4be2-90b3-21fe3613f637

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