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

par Díaz Arado, Oscar;Mönig, Harry;Wagner, Hendrik;Franke, Jorn Holger ;Langewisch, Gernot;Held, Philipp Alexander;Studer, Armido;Fuchs, Harald
Référence ACS Nano, 7, 10, page (8509-8515)
Publication Publié, 2013-10

Article révisé par les pairs

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Résumé :

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. © 2013 American Chemical Society.