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Glaser, Timo ; Meinecke, Jannick ; Freund, Lukas ; Länger, Christian ; Luy, Jan‐Niclas ; Tonner, Ralf ; Koert, Ulrich ; Dürr, Michael

Click Chemistry in Ultra‐high Vacuum – Tetrazine Coupling with Methyl Enol Ether Covalently Linked to Si(001)

Glaser, Timo, Meinecke, Jannick, Freund, Lukas, Länger, Christian, Luy, Jan‐Niclas, Tonner, Ralf, Koert, Ulrich and Dürr, Michael (2021) Click Chemistry in Ultra‐high Vacuum – Tetrazine Coupling with Methyl Enol Ether Covalently Linked to Si(001). Chemistry – A European Journal 27 (31), pp. 8082-8087.

Date of publication of this fulltext: 29 Feb 2024 12:28
Article
DOI to cite this document: 10.5283/epub.56420


Abstract

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 ...

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.



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Details

Item typeArticle
Journal or Publication TitleChemistry – A European Journal
Publisher:Wiley
Place of Publication:WEINHEIM
Volume:27
Number of Issue or Book Chapter:31
Page Range:pp. 8082-8087
Date2021
InstitutionsChemistry and Pharmacy > Institut für Physikalische und Theoretische Chemie
Identification Number
ValueType
10.1002/chem.202005371DOI
KeywordsTOTAL-ENERGY CALCULATIONS; ADSORPTION; SURFACES; FUNCTIONALIZATION; CYCLOOCTYNE; REACTIVITY; click chemistry; density functional calculations; silicon; surface chemistry; X-ray photoelectron spectroscopy
Dewey Decimal Classification500 Science > 540 Chemistry & allied sciences
StatusPublished
RefereedYes, this version has been refereed
Created at the University of RegensburgYes
URN of the UB Regensburgurn:nbn:de:bvb:355-epub-564207
Item ID56420

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