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The additive-free tetrazine/enol ether click reaction was performed inultra-high vacuum (UHV) with an enol ether group covalently linked to a siliconsurface: Dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate molecules were coupled tothe enol ether group of a functionalized cyclooctyne which was adsorbed on thesilicon (001) surface via the strained triple bond of cyclooctyne. The reactionwas observed at a surface temperature of 380 K by means of X-ray photoelectronspectroscopy (XPS). No indications for tetrazine molecules which bind directlyto the Si(001) surface via the nitrogen atoms were detected. A moderate energybarrier was deduced for this click reaction in vacuum by means of densityfunctional theory based calculations, in good agreement with the experimentalresults. This UHV-compatible click reaction thus opens a new, flexible routefor synthesizing covalently bound organic architectures.

Click chemistry in ultra-high vacuum - tetrazine coupling with methyl enol ether covalently linked to Si(001)