Polycyclic aromatic chains on metals and insulating layers by repetitive [3+2] cycloadditions

The vast potential of organic materials for electronic, optoelectronic and spintronic devices entails substantial interest in the fabrication of -conjugated systems with tailored functionality directly at insulating interfaces. On-surface fabrication of such materials on non-metal surfaces remains t...

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Autores: Riss, Alexander, Richter, Marcus, Pérez Paz, Alejandro, Wang, Xiao-Ye, Raju, Rajesh, He, Yuanqin, Ducke, Jacob, Corral, Eduardo, Wuttke, Michael, Seufert, Knud, Garnica, Manuela, Rubio Secades, Angel, Barth, Johannes V., Narita, Akimitsu, Muellen, Klaus, Berger, Reinhard, Feng, Xinliang, Palma, Carlos Andres, Auwärter, Willi
Formato: artículo
Fecha de publicación:2020
País:España
Recursos:Universidad del País Vasco
Repositorio:Addi. Archivo Digital para la Docencia y la Investigación
OAI Identifier:oai:addi.ehu.eus:10810/42719
Acesso em linha:http://hdl.handle.net/10810/42719
Access Level:acceso abierto
Palavra-chave:azide-alkyne cycloaddition
total-energy calculations
on-surface synthesis
boron-nitride
1,3-dipolar cycloadditions
azomethine ylides
graphene
dehalogenation
algorithm
CU(111)
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oai_identifier_str oai:addi.ehu.eus:10810/42719
network_acronym_str ES
network_name_str España
repository_id_str
spelling Polycyclic aromatic chains on metals and insulating layers by repetitive [3+2] cycloadditionsRiss, AlexanderRichter, MarcusPérez Paz, AlejandroWang, Xiao-YeRaju, RajeshHe, YuanqinDucke, JacobCorral, EduardoWuttke, MichaelSeufert, KnudGarnica, ManuelaRubio Secades, AngelBarth, Johannes V.Narita, AkimitsuMuellen, KlausBerger, ReinhardFeng, XinliangPalma, Carlos AndresAuwärter, Williazide-alkyne cycloadditiontotal-energy calculationson-surface synthesisboron-nitride1,3-dipolar cycloadditionsazomethine ylidesgraphenedehalogenationalgorithmCU(111)The vast potential of organic materials for electronic, optoelectronic and spintronic devices entails substantial interest in the fabrication of -conjugated systems with tailored functionality directly at insulating interfaces. On-surface fabrication of such materials on non-metal surfaces remains to be demonstrated with high yield and selectivity. Here we present the synthesis of polyaromatic chains on metallic substrates, insulating layers, and in the solid state. Scanning probe microscopy shows the formation of azaullazine repeating units on Au(111), Ag(111), and h-BN/Cu(111), stemming from intermolecular homo-coupling via cycloaddition reactions of CN-substituted polycyclic aromatic azomethine ylide (PAMY) intermediates followed by subsequent dehydrogenation. Matrix-assisted laser desorption/ionization (MALDI) mass spectrometry demonstrates that the reaction also takes place in the solid state in the absence of any catalyst. Such intermolecular cycloaddition reactions are promising methods for direct synthesis of regioregular polyaromatic polymers on arbitrary insulating surfaces. p id=Par A critical milestone for the advancement of nanoscale organic circuitry is the fabrication of well-defined conjugated polymers on non-metal substrates. Here, the authors demonstrate extended polycyclic aromatic chains from repetitive cycloadditions which form not only on metals, but also on boron nitride layers and in the solid state.This work was financially supported by the European Research Council Consolidator Grant NanoSurfs (no. 615233), the Horizon 2020 research and innovation program 2D ink (no. 664878) and the National Science Foundation of China (no. 11974403 and SinoGerman Project no. 51761135130). W.A. acknowledges funding by the DFG via a Heisenberg professorship. M.R., R.B., and X.F. thank the German Research Foundation (DFG) within the Cluster of Excellence "Center for Advancing Electronics Dresden (cfaed)" and EnhanceNano (No. 391979941). M.G. acknowledges funding by the H2020MSCA-IF-2014 program under GA no. 658070 (2DNano).Nature PublishingEuropean Commission202020202020info:eu-repo/semantics/articleapplication/pdfhttp://hdl.handle.net/10810/42719reponame:Addi. Archivo Digital para la Docencia y la Investigacióninstname:Universidad del País VascoInglésinfo:eu-repo/grantAgreement/EC/FP7/615233info:eu-repo/grantAgreement/EC/H2020/664878info:eu-repo/grantAgreement/EC/H2020/658070https://www.nature.com/articles/s41467-020-15210-2info:eu-repo/semantics/openAccesshttp://creativecommons.org/licenses/by/3.0/es/This article is licensed under a Creative Commons Attribution 4.0 International License. (CC BY 4.0)Atribución 3.0 Españaoai:addi.ehu.eus:10810/427192026-06-18T09:23:17Z
dc.title.none.fl_str_mv Polycyclic aromatic chains on metals and insulating layers by repetitive [3+2] cycloadditions
title Polycyclic aromatic chains on metals and insulating layers by repetitive [3+2] cycloadditions
spellingShingle Polycyclic aromatic chains on metals and insulating layers by repetitive [3+2] cycloadditions
Riss, Alexander
azide-alkyne cycloaddition
total-energy calculations
on-surface synthesis
boron-nitride
1,3-dipolar cycloadditions
azomethine ylides
graphene
dehalogenation
algorithm
CU(111)
title_short Polycyclic aromatic chains on metals and insulating layers by repetitive [3+2] cycloadditions
title_full Polycyclic aromatic chains on metals and insulating layers by repetitive [3+2] cycloadditions
title_fullStr Polycyclic aromatic chains on metals and insulating layers by repetitive [3+2] cycloadditions
title_full_unstemmed Polycyclic aromatic chains on metals and insulating layers by repetitive [3+2] cycloadditions
title_sort Polycyclic aromatic chains on metals and insulating layers by repetitive [3+2] cycloadditions
dc.creator.none.fl_str_mv Riss, Alexander
Richter, Marcus
Pérez Paz, Alejandro
Wang, Xiao-Ye
Raju, Rajesh
He, Yuanqin
Ducke, Jacob
Corral, Eduardo
Wuttke, Michael
Seufert, Knud
Garnica, Manuela
Rubio Secades, Angel
Barth, Johannes V.
Narita, Akimitsu
Muellen, Klaus
Berger, Reinhard
Feng, Xinliang
Palma, Carlos Andres
Auwärter, Willi
author Riss, Alexander
author_facet Riss, Alexander
Richter, Marcus
Pérez Paz, Alejandro
Wang, Xiao-Ye
Raju, Rajesh
He, Yuanqin
Ducke, Jacob
Corral, Eduardo
Wuttke, Michael
Seufert, Knud
Garnica, Manuela
Rubio Secades, Angel
Barth, Johannes V.
Narita, Akimitsu
Muellen, Klaus
Berger, Reinhard
Feng, Xinliang
Palma, Carlos Andres
Auwärter, Willi
author_role author
author2 Richter, Marcus
Pérez Paz, Alejandro
Wang, Xiao-Ye
Raju, Rajesh
He, Yuanqin
Ducke, Jacob
Corral, Eduardo
Wuttke, Michael
Seufert, Knud
Garnica, Manuela
Rubio Secades, Angel
Barth, Johannes V.
Narita, Akimitsu
Muellen, Klaus
Berger, Reinhard
Feng, Xinliang
Palma, Carlos Andres
Auwärter, Willi
author2_role author
author
author
author
author
author
author
author
author
author
author
author
author
author
author
author
author
author
dc.contributor.none.fl_str_mv European Commission
dc.subject.none.fl_str_mv azide-alkyne cycloaddition
total-energy calculations
on-surface synthesis
boron-nitride
1,3-dipolar cycloadditions
azomethine ylides
graphene
dehalogenation
algorithm
CU(111)
topic azide-alkyne cycloaddition
total-energy calculations
on-surface synthesis
boron-nitride
1,3-dipolar cycloadditions
azomethine ylides
graphene
dehalogenation
algorithm
CU(111)
description The vast potential of organic materials for electronic, optoelectronic and spintronic devices entails substantial interest in the fabrication of -conjugated systems with tailored functionality directly at insulating interfaces. On-surface fabrication of such materials on non-metal surfaces remains to be demonstrated with high yield and selectivity. Here we present the synthesis of polyaromatic chains on metallic substrates, insulating layers, and in the solid state. Scanning probe microscopy shows the formation of azaullazine repeating units on Au(111), Ag(111), and h-BN/Cu(111), stemming from intermolecular homo-coupling via cycloaddition reactions of CN-substituted polycyclic aromatic azomethine ylide (PAMY) intermediates followed by subsequent dehydrogenation. Matrix-assisted laser desorption/ionization (MALDI) mass spectrometry demonstrates that the reaction also takes place in the solid state in the absence of any catalyst. Such intermolecular cycloaddition reactions are promising methods for direct synthesis of regioregular polyaromatic polymers on arbitrary insulating surfaces. p id=Par A critical milestone for the advancement of nanoscale organic circuitry is the fabrication of well-defined conjugated polymers on non-metal substrates. Here, the authors demonstrate extended polycyclic aromatic chains from repetitive cycloadditions which form not only on metals, but also on boron nitride layers and in the solid state.
publishDate 2020
dc.date.none.fl_str_mv 2020
2020
2020
dc.type.none.fl_str_mv info:eu-repo/semantics/article
format article
dc.identifier.none.fl_str_mv http://hdl.handle.net/10810/42719
url http://hdl.handle.net/10810/42719
dc.language.none.fl_str_mv Inglés
language_invalid_str_mv Inglés
dc.relation.none.fl_str_mv info:eu-repo/grantAgreement/EC/FP7/615233
info:eu-repo/grantAgreement/EC/H2020/664878
info:eu-repo/grantAgreement/EC/H2020/658070
https://www.nature.com/articles/s41467-020-15210-2
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
http://creativecommons.org/licenses/by/3.0/es/
Atribución 3.0 España
eu_rights_str_mv openAccess
rights_invalid_str_mv http://creativecommons.org/licenses/by/3.0/es/
Atribución 3.0 España
dc.format.none.fl_str_mv application/pdf
dc.publisher.none.fl_str_mv Nature Publishing
publisher.none.fl_str_mv Nature Publishing
dc.source.none.fl_str_mv reponame:Addi. Archivo Digital para la Docencia y la Investigación
instname:Universidad del País Vasco
instname_str Universidad del País Vasco
reponame_str Addi. Archivo Digital para la Docencia y la Investigación
collection Addi. Archivo Digital para la Docencia y la Investigación
repository.name.fl_str_mv
repository.mail.fl_str_mv
_version_ 1869403708052209664
score 15,198674

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