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Highly Stereospecific On‐Surface Dimerization into Bishelicenes: Topochemical Ullmann Coupling of Bromohelicene on Au(111)


Voigt, Jan; Martin, Kévin; Neziri, Egzona; Baljozović, Miloš; Wäckerlin, Christian; Avarvari, Narcis; Ernst, Karl‐Heinz (2023). Highly Stereospecific On‐Surface Dimerization into Bishelicenes: Topochemical Ullmann Coupling of Bromohelicene on Au(111). Chemistry, 29(28):e202300134.

Abstract

The on‐surface dimerization into bis(hexahelicene) on a gold(111) surface has been studied by means of scanning tunneling microscopy and time‐of‐flight secondary mass spectrometry. C−C Ullmann coupling of (rac)‐2‐bromo‐hexahelicene leads to formation of the (M,M)‐ and (P,P)‐diastereomers of 2,2’‐bis(hexahelicene), whilst formation of the (M,P)‐diastereomer is not observed. Upon cooling, the bis(hexahelicene) aggregates into an ordered two‐dimensional lattice with partly randomly distributed enantiomers. The highly specific diastereomeric coupling is explained by the surface alignment of educt in combination with the strong steric overcrowding in a possible surface‐confined (M,P)‐product.

Abstract

The on‐surface dimerization into bis(hexahelicene) on a gold(111) surface has been studied by means of scanning tunneling microscopy and time‐of‐flight secondary mass spectrometry. C−C Ullmann coupling of (rac)‐2‐bromo‐hexahelicene leads to formation of the (M,M)‐ and (P,P)‐diastereomers of 2,2’‐bis(hexahelicene), whilst formation of the (M,P)‐diastereomer is not observed. Upon cooling, the bis(hexahelicene) aggregates into an ordered two‐dimensional lattice with partly randomly distributed enantiomers. The highly specific diastereomeric coupling is explained by the surface alignment of educt in combination with the strong steric overcrowding in a possible surface‐confined (M,P)‐product.

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Additional indexing

Item Type:Journal Article, refereed, original work
Communities & Collections:07 Faculty of Science > Department of Chemistry
Dewey Decimal Classification:540 Chemistry
Scopus Subject Areas:Physical Sciences > Catalysis
Physical Sciences > General Chemistry
Physical Sciences > Organic Chemistry
Uncontrolled Keywords:General Chemistry, Catalysis, Organic Chemistry
Language:English
Date:16 May 2023
Deposited On:18 Feb 2024 15:13
Last Modified:30 Jun 2024 03:32
Publisher:Wiley-Blackwell Publishing, Inc.
ISSN:0947-6539
OA Status:Hybrid
Publisher DOI:https://doi.org/10.1002/chem.202300134
PubMed ID:36856040
Project Information:
  • : FunderSNSF
  • : Grant ID182082
  • : Project TitleAdvanced Molecular Chiral Surface Systems
  • Content: Published Version
  • Language: English
  • Licence: Creative Commons: Attribution 4.0 International (CC BY 4.0)