Exploring the impact of select anchor groups for norbornadiene/quadricyclane single-molecule switches
To achieve the ultimate limit of device miniaturization, it is necessary to have a comprehensive understanding of the structure-property relationship in functional molecular systems used in single-molecule electronics. This study reports the synthesis and characterization of a novel series of norbor...
| Autores: | , , , , , , , , , , , , , , |
|---|---|
| Formato: | artículo |
| Estado: | Versión publicada |
| Fecha de publicación: | 2023 |
| País: | España |
| Recursos: | Consejo Superior de Investigaciones Científicas (CSIC) |
| Repositorio: | DIGITAL.CSIC. Repositorio Institucional del CSIC |
| OAI Identifier: | oai:digital.csic.es:10261/341521 |
| Acesso em linha: | http://hdl.handle.net/10261/341521 https://api.elsevier.com/content/abstract/scopus_id/85175265367 |
| Access Level: | acceso abierto |
| Palavra-chave: | Charge-transport Conductance Norbornadiene |
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Exploring the impact of select anchor groups for norbornadiene/quadricyclane single-molecule switchesGhasemi, ShimaOrnago, LucaLiasi, ZachariasJohansen, Magnus BukhaveBuchwald, Theo Juncker vonHillers-Bendtsen, Andreas ErbsPoel, Sebastiaan van derHölzel, HelenWang, ZhihangAmombo Noa, Francoise M.Öhrström, LarsMikkelsen, Kurt V.Zant, Herre S.J. van derLara Avila, SamuelMoth-Poulsen, KasperCharge-transportConductanceNorbornadieneTo achieve the ultimate limit of device miniaturization, it is necessary to have a comprehensive understanding of the structure-property relationship in functional molecular systems used in single-molecule electronics. This study reports the synthesis and characterization of a novel series of norbornadiene derivatives capped with thioether and thioester anchor groups. Utilizing the mechanically controllable break junction technique, the impact of these capping groups on conductance across single-molecule junctions is investigated. Among the selection of anchor groups, norbornadiene capped with thioacetate and tert-butyl groups exhibits higher conductance (G ≈ 4 × 10−4 G0) compared to methyl thioether (G ≈ 2 × 10−4 G0). Electronic transmission through the considered set of single-molecule junctions has been simulated. The computational results for electron transport across these junctions align closely with the experimental findings, with the thioacetate- and tert-butyl-substituted systems outperforming the methyl thioether-capped derivative. In terms of junction stability, the methyl thioether-capped system is the most resilient, maintaining consistent conductance even after approximately 10 000 cycles. Meanwhile, the likelihood of observing molecular plateaus in both the thioacetate- and tert-butyl-substituted systems declines over time. These findings substantially advance both the design and understanding of functional molecular systems in the realm of single-molecule electronics, particularly in the context of molecular photoswitches.KMP acknowledges funding from the Catalan Institution for Research and Advanced Studies (ICREA), the European Research Council (ERC) through ERC-CoG PHOTHERM, and the European Union project ESiM 101046364. The Swedish NMR Centre at the University of Gothenburg is acknowledged for its support.With funding from the Spanish government through the ‘Severo Ochoa Centre of Excellence’ accreditation (CEX2019-000917-S).Peer reviewedRoyal Society of Chemistry (UK)ICREA AcadèmiaEuropean Research CouncilEuropean CommissionAgencia Estatal de Investigación (España)Ghasemi, Shima [0000-0001-7915-1546]Ornago, Luca [0000-0001-5293-2887]Liasi, Zacharias [0000-0001-6722-5640]Johansen, Magnus Bukhave [0000-0002-4321-4493]Buchwald, Theo Juncker von [0000-0002-4812-7073]Hillers-Bendtsen, Andreas Erbs [0000-0003-4960-8802]Poel, Sebastiaan van der [0009-0009-6323-3665]Hölzel, Helen [0000-0003-2312-9934]Wang, Zhihang [0000-0002-9961-3346]Amombo Noa, Francoise M. [0000-0001-8361-3432]Öhrström, Lars [0000-0002-6420-2141]Mikkelsen, Kurt V. [0000-0003-4090-7697]Zant, Herre S.J. van der [0000-0002-5385-0282]Lara Avila, Samuel [0000-0002-8331-718X]Moth-Poulsen, Kasper [0000-0003-4018-4927]Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72]202420242023info:eu-repo/semantics/articlehttp://purl.org/coar/resource_type/c_6501Publisher's versioninfo:eu-repo/semantics/publishedVersionhttp://hdl.handle.net/10261/341521https://api.elsevier.com/content/abstract/scopus_id/85175265367reponame: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#info:eu-repo/grantAgreement/EC/H2020/101002131info:eu-repo/grantAgreement/EC/HE/101046364info:eu-repo/grantAgreement/AEI/Plan Estatal de investigación Científica y Técnica y de Innovación 2017-2020/CEX2019-000917-SJournal of Materials Chemistry Chttp://doi.org/10.1039/d3tc02652cSíinfo:eu-repo/semantics/openAccessoai:digital.csic.es:10261/3415212026-05-22T06:33:51Z |
| dc.title.none.fl_str_mv |
Exploring the impact of select anchor groups for norbornadiene/quadricyclane single-molecule switches |
| title |
Exploring the impact of select anchor groups for norbornadiene/quadricyclane single-molecule switches |
| spellingShingle |
Exploring the impact of select anchor groups for norbornadiene/quadricyclane single-molecule switches Ghasemi, Shima Charge-transport Conductance Norbornadiene |
| title_short |
Exploring the impact of select anchor groups for norbornadiene/quadricyclane single-molecule switches |
| title_full |
Exploring the impact of select anchor groups for norbornadiene/quadricyclane single-molecule switches |
| title_fullStr |
Exploring the impact of select anchor groups for norbornadiene/quadricyclane single-molecule switches |
| title_full_unstemmed |
Exploring the impact of select anchor groups for norbornadiene/quadricyclane single-molecule switches |
| title_sort |
Exploring the impact of select anchor groups for norbornadiene/quadricyclane single-molecule switches |
| dc.creator.none.fl_str_mv |
Ghasemi, Shima Ornago, Luca Liasi, Zacharias Johansen, Magnus Bukhave Buchwald, Theo Juncker von Hillers-Bendtsen, Andreas Erbs Poel, Sebastiaan van der Hölzel, Helen Wang, Zhihang Amombo Noa, Francoise M. Öhrström, Lars Mikkelsen, Kurt V. Zant, Herre S.J. van der Lara Avila, Samuel Moth-Poulsen, Kasper |
| author |
Ghasemi, Shima |
| author_facet |
Ghasemi, Shima Ornago, Luca Liasi, Zacharias Johansen, Magnus Bukhave Buchwald, Theo Juncker von Hillers-Bendtsen, Andreas Erbs Poel, Sebastiaan van der Hölzel, Helen Wang, Zhihang Amombo Noa, Francoise M. Öhrström, Lars Mikkelsen, Kurt V. Zant, Herre S.J. van der Lara Avila, Samuel Moth-Poulsen, Kasper |
| author_role |
author |
| author2 |
Ornago, Luca Liasi, Zacharias Johansen, Magnus Bukhave Buchwald, Theo Juncker von Hillers-Bendtsen, Andreas Erbs Poel, Sebastiaan van der Hölzel, Helen Wang, Zhihang Amombo Noa, Francoise M. Öhrström, Lars Mikkelsen, Kurt V. Zant, Herre S.J. van der Lara Avila, Samuel Moth-Poulsen, Kasper |
| author2_role |
author author author author author author author author author author author author author author |
| dc.contributor.none.fl_str_mv |
ICREA Acadèmia European Research Council European Commission Agencia Estatal de Investigación (España) Ghasemi, Shima [0000-0001-7915-1546] Ornago, Luca [0000-0001-5293-2887] Liasi, Zacharias [0000-0001-6722-5640] Johansen, Magnus Bukhave [0000-0002-4321-4493] Buchwald, Theo Juncker von [0000-0002-4812-7073] Hillers-Bendtsen, Andreas Erbs [0000-0003-4960-8802] Poel, Sebastiaan van der [0009-0009-6323-3665] Hölzel, Helen [0000-0003-2312-9934] Wang, Zhihang [0000-0002-9961-3346] Amombo Noa, Francoise M. [0000-0001-8361-3432] Öhrström, Lars [0000-0002-6420-2141] Mikkelsen, Kurt V. [0000-0003-4090-7697] Zant, Herre S.J. van der [0000-0002-5385-0282] Lara Avila, Samuel [0000-0002-8331-718X] Moth-Poulsen, Kasper [0000-0003-4018-4927] Consejo Superior de Investigaciones Científicas [https://ror.org/02gfc7t72] |
| dc.subject.none.fl_str_mv |
Charge-transport Conductance Norbornadiene |
| topic |
Charge-transport Conductance Norbornadiene |
| description |
To achieve the ultimate limit of device miniaturization, it is necessary to have a comprehensive understanding of the structure-property relationship in functional molecular systems used in single-molecule electronics. This study reports the synthesis and characterization of a novel series of norbornadiene derivatives capped with thioether and thioester anchor groups. Utilizing the mechanically controllable break junction technique, the impact of these capping groups on conductance across single-molecule junctions is investigated. Among the selection of anchor groups, norbornadiene capped with thioacetate and tert-butyl groups exhibits higher conductance (G ≈ 4 × 10−4 G0) compared to methyl thioether (G ≈ 2 × 10−4 G0). Electronic transmission through the considered set of single-molecule junctions has been simulated. The computational results for electron transport across these junctions align closely with the experimental findings, with the thioacetate- and tert-butyl-substituted systems outperforming the methyl thioether-capped derivative. In terms of junction stability, the methyl thioether-capped system is the most resilient, maintaining consistent conductance even after approximately 10 000 cycles. Meanwhile, the likelihood of observing molecular plateaus in both the thioacetate- and tert-butyl-substituted systems declines over time. These findings substantially advance both the design and understanding of functional molecular systems in the realm of single-molecule electronics, particularly in the context of molecular photoswitches. |
| publishDate |
2023 |
| dc.date.none.fl_str_mv |
2023 2024 2024 |
| 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 |
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publishedVersion |
| dc.identifier.none.fl_str_mv |
http://hdl.handle.net/10261/341521 https://api.elsevier.com/content/abstract/scopus_id/85175265367 |
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http://hdl.handle.net/10261/341521 https://api.elsevier.com/content/abstract/scopus_id/85175265367 |
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Inglés |
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Inglés |
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#PLACEHOLDER_PARENT_METADATA_VALUE# #PLACEHOLDER_PARENT_METADATA_VALUE# #PLACEHOLDER_PARENT_METADATA_VALUE# info:eu-repo/grantAgreement/EC/H2020/101002131 info:eu-repo/grantAgreement/EC/HE/101046364 info:eu-repo/grantAgreement/AEI/Plan Estatal de investigación Científica y Técnica y de Innovación 2017-2020/CEX2019-000917-S Journal of Materials Chemistry C http://doi.org/10.1039/d3tc02652c Sí |
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info:eu-repo/semantics/openAccess |
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openAccess |
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Royal Society of Chemistry (UK) |
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Royal Society of Chemistry (UK) |
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reponame:DIGITAL.CSIC. Repositorio Institucional del CSIC instname:Consejo Superior de Investigaciones Científicas (CSIC) |
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Consejo Superior de Investigaciones Científicas (CSIC) |
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DIGITAL.CSIC. Repositorio Institucional del CSIC |
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DIGITAL.CSIC. Repositorio Institucional del CSIC |
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