Reaction Selectivity in On-Surface Chemistry by Surface Coverage Control-Alkyne Dimerization versus Alkyne Trimerization

被引：11

作者：

Klaasen, Henning ^{[1
]}

Liu, Lacheng ^{[2
,3
]}

Meng, Xiangzhi ^{[2
,3
]}

Held, Philipp Alexander ^{[1
]}

Gao, Hong-Ying ^{[2
,3
]}

Barton, Dennis ^{[1
,4
,5
]}

Mueck-Lichtenfeld, Christian ^{[1
,4
]}

Neugebauer, Johannes ^{[1
,4
]}

Fuchs, Harald ^{[2
,3
]}

Studer, Armido ^{[1
]}

机构：

[1] Westfalische Wilhelms Univ Munster, Organ Chem Inst, Correnstr 40, D-48149 Munster, Germany

[2] Westfalische Wilhelms Univ Munster, Phys Inst, Wilhelm Klemm Str 10, D-48149 Munster, Germany

[3] Ctr Nanotechnol CeNTech, Heisenbergstr 11, D-48149 Munster, Germany

[4] Westfalische Wilhelms Univ Munster, Ctr Multiscale Theory & Computat, Corrensstr 40, D-48149 Munster, Germany

[5] Univ Luxembourg, Phys & Mat Sci Res Unit, 162 A Ave Faiencerie, L-1511 Luxembourg, Luxembourg

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2018年 / 24卷 / 57期

关键词：

arenes; homocoupling; self assembly; silver; surface chemistry; COVALENT ORGANIC FRAMEWORKS; ULTRAHIGH-VACUUM; METAL-SURFACES; AU(111); POLYMER; ACID; CYCLOADDITION; FABRICATION; MECHANISM; NETWORKS;

D O I：

10.1002/chem.201802848

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

This work reports the influence of molecular coverage in on-surface C-C-bond formation on reaction outcome. 6-Ethynyl-2-naphthoic acid (ENA) was chosen as organic component and Ag(111) as substrate. The alkyne moiety in ENA can either react by dimerization to ENA dimers (Glaser coupling or hydroalkynylation) or cyclotrimerization to generate a benzene core as connecting moiety. Dimer formation is preferred at high surface coverage whereas trimerization is the major reaction pathway at low coverage. Mechanistic studies are provided.

引用

页码：15303 / 15308

页数：6

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