Click Chemistry in Ultra‐high Vacuum – Tetrazine Coupling with Methyl Enol Ether Covalently Linked to Si(001)
| Autor: | Ralf Tonner, Michael Dürr, Lukas Freund, Christian Länger, Jan-Niclas Luy, Timo Glaser, Jannick Meinecke, Ulrich Koert |
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| Rok vydání: | 2021 |
| Předmět: |
X-ray photoelectron spectroscopy
Ultra-high vacuum surface chemistry 010402 general chemistry 01 natural sciences Catalysis Tetrazine chemistry.chemical_compound Polymer chemistry Molecule chemistry.chemical_classification 010405 organic chemistry Communication Organic Chemistry silicon General Chemistry Triple bond Communications 0104 chemical sciences chemistry Covalent bond click chemistry density functional calculations Click chemistry Enol ether |
| Zdroj: | Chemistry (Weinheim an Der Bergstrasse, Germany) |
| ISSN: | 1521-3765 0947-6539 |
| DOI: | 10.1002/chem.202005371 |
| Popis: | 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. Catalyst‐free coupling of a tetrazine derivative and an enol ether group, the latter being covalently attached on a Si(001) surface via cyclooctyne, has been observed in ultra‐high vacuum by X‐ray photoelectron spectroscopy. DFT calculations identified the associated reaction meachanism. This click chemistry scheme allows the synthesis of covalently bound molecular architectures on highly reactive surfaces in a UHV environment. |
| Databáze: | OpenAIRE |
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