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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 und 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), S. 8082-8087.

Veröffentlichungsdatum dieses Volltextes: 29 Feb 2024 12:28
Artikel
DOI zum Zitieren dieses Dokuments: 10.5283/epub.56420


Zusammenfassung

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

DokumentenartArtikel
Titel eines Journals oder einer ZeitschriftChemistry – A European Journal
Verlag:Wiley
Ort der Veröffentlichung:WEINHEIM
Band:27
Nummer des Zeitschriftenheftes oder des Kapitels:31
Seitenbereich:S. 8082-8087
Datum2021
InstitutionenChemie und Pharmazie > Institut für Physikalische und Theoretische Chemie
Identifikationsnummer
WertTyp
10.1002/chem.202005371DOI
Stichwörter / KeywordsTOTAL-ENERGY CALCULATIONS; ADSORPTION; SURFACES; FUNCTIONALIZATION; CYCLOOCTYNE; REACTIVITY; click chemistry; density functional calculations; silicon; surface chemistry; X-ray photoelectron spectroscopy
Dewey-Dezimal-Klassifikation500 Naturwissenschaften und Mathematik > 540 Chemie
StatusVeröffentlicht
BegutachtetJa, diese Version wurde begutachtet
An der Universität Regensburg entstandenJa
URN der UB Regensburgurn:nbn:de:bvb:355-epub-564207
Dokumenten-ID56420

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