The additive-free tetrazine/enol ether click reaction was performed in ultra-high vacuum (UHV) with an enol ether group covalently linked to a silicon surface: Dimethyl 1,2,4,5-tetrazine-3,6-dicarboxylate molecules were coupled to the enol ether group of a functionalized cyclooctyne which was adsorbed on the silicon (001) surface via the strained triple bond of cyclooctyne. The reaction was observed at a substrate temperature of 380 K by means of X-ray photoelectron spectroscopy (XPS). A moderate energy barrier was deduced for this click reaction in vacuum by means of density functional theory based calculations, in good agreement with the experimental results. This UHV-compatible click reaction thus opens a new, flexible route for synthesizing covalently bound organic architectures.
The additive-free tetrazine/enol ether click reaction was performed in ultra-high vacuum (UHV) with an enol ether group covalently linked to a silicon surface: Dimethyl 1,2,4,5-tetrazine-3,6dicarboxylate molecules were coupled to the enol ether group of a functionalized cyclooctyne which was adsorbed on the silicon (001) surface via the strained triple bond of cyclooctyne. The reaction was observed at a surface temperature of 380 K by means of X-ray photoelectron spectroscopy (XPS). No indications for tetrazine molecules which bind directly to the Si(001) surface via the nitrogen atoms were detected. A moderate energy barrier was deduced for this click reaction in vacuum by means of density functional theory based calculations, in good agreement with the experimental results. This UHV-compatible click reaction thus opens a new, flexible route for synthesizing covalently bound organic architectures.
Let it click in UHV: a click chemistry reaction suitable for application under ultra‐high vacuum (UHV) conditions was developed based on enolether/tetrazine coupling. It is orthogonal to the strain‐promoted cycloaddition of cyclooctynes to azides and allows for tailored layer‐by‐layer synthesis on highly reactive semiconductor surfaces such as Si(001) seen through the window of a UHV apparatus. More information can be found in the Communication by M. Dürr et al. (DOI: 10.1002/chem.202005371).
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