On-surface azide-alkyne cycloaddition on Au(111).

Díaz Arado, Oscar; Mönig, Harry; Wagner, Hendrik; Franke, Jörn-Holger; Langewisch, Gernot; Held, Philipp Alexander; Studer, Armido; Fuchs, Harald · ACS Nano · 2013

basic_science · Level V

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Abstract

We present [3 + 2] cycloaddition reactions between azides and alkynes on a Au(111) surface at room temperature and under ultrahigh vacuum conditions. High-resolution scanning tunneling microscopy images reveal that these on-surface cycloadditions occur highly regioselectively to form the corresponding 1,4-triazoles. Density functional theory simulations confirm that the reactions can occur at room temperature, where the Au(111) surface does not participate as a catalytic agent in alkyne C-H activation but acts solely as a two-dimensional constraint for the positioning of the two reaction partners. The on-surface azide-alkyne cycloaddition offers great potential toward the development and fabrication of functional organic nanomaterials on surfaces.