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Click Chemistry in Ultra‐high Vacuum – Tetrazine Coupling with Methyl Enol Ether Covalently Linked to Si(001)
Author(s) -
Glaser Timo,
Meinecke Jannick,
Freund Lukas,
Länger Christian,
Luy JanNiclas,
Tonner Ralf,
Koert Ulrich,
Dürr Michael
Publication year - 2021
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.202005371
Subject(s) - covalent bond , tetrazine , x ray photoelectron spectroscopy , chemistry , click chemistry , molecule , coupling reaction , enol , enol ether , photochemistry , computational chemistry , crystallography , polymer chemistry , organic chemistry , nuclear magnetic resonance , physics , catalysis
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.