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超高真空中的点击化学——四嗪与共价连接到Si(001)的甲基烯醇醚的偶联

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

作者信息

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

机构信息

Institut für Angewandte Physik and Zentrum für Materialforschung, Justus-Liebig-Universität Giessen, 35392, Giessen, Germany.

Fachbereich Chemie, Philipps-Universität Marburg, 35032, Marburg, Germany.

出版信息

Chemistry. 2021 Jun 1;27(31):8082-8087. doi: 10.1002/chem.202005371. Epub 2021 May 7.

DOI:10.1002/chem.202005371
PMID:33848381
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC8252806/
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 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.

摘要

无添加剂的四嗪/烯醇醚点击反应在超高真空（UHV）中进行，烯醇醚基团共价连接到硅表面：1,2,4,5-四嗪-3,6-二甲酸二甲酯分子与功能化环辛炔的烯醇醚基团偶联，该环辛炔通过环辛炔的张力三键吸附在硅（001）表面。通过X射线光电子能谱（XPS）在380 K的底物温度下观察到该反应。通过基于密度泛函理论的计算推断出该点击反应在真空中存在适度的能垒，这与实验结果高度吻合。这种与超高真空兼容的点击反应因此为合成共价结合的有机结构开辟了一条新的、灵活的途径。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b12b/8252806/039643d6d20b/CHEM-27-8082-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b12b/8252806/438765f23daa/CHEM-27-8082-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b12b/8252806/63906df601e1/CHEM-27-8082-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b12b/8252806/f695caf2c4ee/CHEM-27-8082-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b12b/8252806/9d1e09566e1a/CHEM-27-8082-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b12b/8252806/d69b791c94df/CHEM-27-8082-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b12b/8252806/039643d6d20b/CHEM-27-8082-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b12b/8252806/438765f23daa/CHEM-27-8082-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b12b/8252806/63906df601e1/CHEM-27-8082-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b12b/8252806/f695caf2c4ee/CHEM-27-8082-g001.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b12b/8252806/9d1e09566e1a/CHEM-27-8082-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b12b/8252806/d69b791c94df/CHEM-27-8082-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/b12b/8252806/039643d6d20b/CHEM-27-8082-g005.jpg

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