Highly Stereospecific On-Surface Dimerization into Bishelicenes: Topochemical Ullmann Coupling of Bromohelicene on Au(111) - Université d'Angers Accéder directement au contenu
Article Dans Une Revue Chemistry - A European Journal Année : 2023

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

Résumé

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. Supporting information for this article is given via a link at the end of the document.

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Chimie
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Dates et versions

hal-04306034 , version 1 (24-11-2023)

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Jan Voigt, Kévin Martin, Egzona Neziri, Miloš Baljozović, Christian Wäckerlin, et al.. Highly Stereospecific On-Surface Dimerization into Bishelicenes: Topochemical Ullmann Coupling of Bromohelicene on Au(111). Chemistry - A European Journal, 2023, 29 (28), ⟨10.1002/chem.202300134⟩. ⟨hal-04306034⟩
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