Hierarchy in the Halogen Activation During Surface-Promoted Ullmann Coupling.
Ullmann coupling
density functional calculations
graphene nanoribbons
hierarchical synthesis
scanning probe microscopy
Journal
Chemphyschem : a European journal of chemical physics and physical chemistry
ISSN: 1439-7641
Titre abrégé: Chemphyschem
Pays: Germany
ID NLM: 100954211
Informations de publication
Date de publication:
17 09 2019
17 09 2019
Historique:
received:
27
06
2019
pubmed:
23
7
2019
medline:
23
7
2019
entrez:
23
7
2019
Statut:
ppublish
Résumé
Within the collection of surface-supported reactions currently accessible for the production of extended molecular nanostructures under ultra-high vacuum, Ullmann coupling has been the most successful in the controlled formation of covalent single C-C bonds. Particularly advanced control of this synthetic tool has been obtained by means of hierarchical reactivity, commonly achieved by the use of different halogen atoms that consequently display distinct activation temperatures. Here we report on the site-selective reactivity of certain carbon-halogen bonds. We use precursor molecules halogenated with bromine atoms at two non-equivalent carbon atoms and found that the Ullmann coupling occurs on Au(111) with a remarkable predilection for one of the positions. Experimental evidence is provided by means of scanning tunneling microscopy and core level photoemission spectroscopy, and a rationalized understanding of the observed preference is obtained from density functional theory calculations.
Identifiants
pubmed: 31328365
doi: 10.1002/cphc.201900633
doi:
Types de publication
Journal Article
Research Support, Non-U.S. Gov't
Langues
eng
Sous-ensembles de citation
IM
Pagination
2305-2310Subventions
Organisme : European Research Council (ERC)
Pays : International
Organisme : European Union's Horizon 2020 research and innovation programme
ID : 635919
Pays : International
Organisme : Spanish Ministry of Economy, Industry and Competitiveness
ID : MAT2016-78293-C6-R
Pays : International
Organisme : Xunta de Galicia
ID : ED431G/09
Pays : International
Organisme : Fondo Europeo de Desarrollo Regional (FEDER)
Pays : International
Organisme : "Imbabura" computer cluster of Yachay Tech University
ID : 2017-024 (SIE-UITEY-007-2017)
Pays : International
Informations de copyright
© 2019 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.
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