On-surface azide-alkyne cycloaddition on Cu(111): does it “click” in ultrahigh vacuum?

Bebensee F, Bombis C, Vadapoo SR, Cramer JR, Besenbacher F, Gothelf KV, Linderoth TR.

J Am Chem Soc. 2013 Feb 13;135(6):2136-9. doi: 10.1021/ja312303a. Epub 2013 Feb 1.

Sino-Danish Center for Molecular Nanostructures on Surfaces, Interdisciplinary Nanoscience Center and Department of Physics and Astronomy, Aarhus University, 8000 Aarhus C, Denmark.

Abstract

Using scanning tunneling microscopy, we demonstrate that the 1,3-dipolar cycloaddition between a terminal alkyne and an azide can be performed under solvent-free ultrahigh vacuum conditions with reactants adsorbed on a Cu(111) surface. XPS shows significant degradation of the azide upon adsorption, which is found to be the limiting factor for the reaction.

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