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

被引：7

作者：

Glaser, Timo ^{[1
,2
]}

Meinecke, Jannick ^{[3
]}

Freund, Lukas ^{[1
,2
]}

Laenger, Christian ^{[1
,2
]}

Luy, Jan-Niclas ^{[3
,4
,5
]}

Tonner, Ralf ^{[3
,4
]}

Koert, Ulrich ^{[3
]}

Duerr, Michael ^{[1
,2
]}

机构：

[1] Justus Liebig Univ Giessen, Inst Angew Phys, D-35392 Giessen, Germany

[2] Justus Liebig Univ Giessen, Zentrum Mat Forsch, D-35392 Giessen, Germany

[3] Philipps Univ Marburg, Fachbereich Chem, D-35032 Marburg, Germany

[4] Univ Regensburg, Fak Chem & Pharm, D-93053 Regensburg, Germany

[5] Univ Leipzig, Wilhelm Ostwald Inst Phys & Theoret Chem, D-04103 Leipzig, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2021年 / 27卷 / 31期

关键词：

click chemistry; density functional calculations; silicon; surface chemistry; X-ray photoelectron spectroscopy; TOTAL-ENERGY CALCULATIONS; ADSORPTION; SURFACES; FUNCTIONALIZATION; CYCLOOCTYNE; REACTIVITY;

D O I：

10.1002/chem.202005371

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

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.

引用

页码：8082 / 8087

页数：6

共 40 条

[1]

[Anonymous], 2007, TURBOMOLE V72 2017

[2]

[Anonymous], 2009, ANGEW CHEM, V121, P7108

[3] On-Surface Azide-Alkyne Cycloaddition on Cu(111): Does It "Click" in Ultrahigh Vacuum? [J].

Bebensee, Fabian ;

Bombis, Christian ;

Vadapoo, Sundar-Raja ;

Cramer, Jacob R. ;

Besenbacher, Flemming ;

Gothelf, Kurt V. ;

Linderoth, Trolle R. .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2013, 135 (06) :2136-2139

[4]

Bertozzi CR, 2001, ANGEW CHEM, V112, P2056

[5] Copper catalyzed azide-alkyne cycloadditions on solid surfaces: Applications and future directions [J].

Devaraj, Neal K. ;

Collman, James P. .

QSAR & COMBINATORIAL SCIENCE, 2007, 26 (11-12) :1253-1260

[6] Solution-Based Alkyne-Azide Coupling on Functionalized Si(001) Prepared under UHV Conditions [J].

Glaser, Timo ;

Meinecke, Jannick ;

Laenger, Christian ;

Heep, Julian ;

Koert, Ulrich ;

Duerr, Michael .

JOURNAL OF PHYSICAL CHEMISTRY C, 2021, 125 (07) :4021-4026

[7] Combined XPS and DFT investigation of the adsorption modes of methyl enol ether functionalized cyclooctyne on Si(001) [J].

Glaser, Timo ;

Meinecke, Jannick ;

Laenger, Christian ;

Luy, Jan-Niclas ;

Tonner, Ralf ;

Koert, Ulrich ;

Duerr, Michael .

CHEMPHYSCHEM, 2021, 22 (04) :404-409

[8] Starting from a Fixed Geometry: Real-Time XPS Investigation of a Surface Reaction with Controlled Molecular Configurations [J].

Glaser, Timo ;

Laenger, Christian ;

Heep, Julian ;

Meinecke, Jannick ;

Silly, Mathieu G. ;

Koert, Ulrich ;

Duerr, Michael .

JOURNAL OF PHYSICAL CHEMISTRY C, 2020, 124 (41) :22619-22624

[9] Functionalization of Azide-Terminated Silicon Surfaces with Glycans Using Click Chemistry: XPS and FTIR Study [J].

Gouget-Laemmel, A. C. ;

Yang, J. ;

Lodhi, M. A. ;

Siriwardena, A. ;

Aureau, D. ;

Boukherroub, R. ;

Chazalviel, J-N. ;

Ozanam, F. ;

Szunerits, S. .

JOURNAL OF PHYSICAL CHEMISTRY C, 2013, 117 (01) :368-375

[10] A consistent and accurate ab initio parametrization of density functional dispersion correction (DFT-D) for the 94 elements H-Pu [J].

Grimme, Stefan ;

Antony, Jens ;

Ehrlich, Stephan ;

Krieg, Helge .

JOURNAL OF CHEMICAL PHYSICS, 2010, 132 (15)

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