Homo-coupling of terminal alkynes on a noble metal surface

Yi-Qi Zhang, Nenad Kepčija, Martin Kleinschrodt, Katharina Diller, Sybille Fischer, Anthoula C. Papageorgiou, Francesco Allegretti, Jonas Björk, Svetlana Klyatskaya, Florian Klappenberger (), Mario Ruben () and Johannes V. Barth
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Yi-Qi Zhang: Technische Universität München
Nenad Kepčija: Technische Universität München
Martin Kleinschrodt: Technische Universität München
Katharina Diller: Technische Universität München
Sybille Fischer: Technische Universität München
Anthoula C. Papageorgiou: Technische Universität München
Francesco Allegretti: Technische Universität München
Jonas Björk: Chemistry and Biology (IFM), Linköping University
Svetlana Klyatskaya: Institute of Nanotechnology (INT), Karlsruhe Institute of Technology (KIT)
Florian Klappenberger: Technische Universität München
Mario Ruben: Institute of Nanotechnology (INT), Karlsruhe Institute of Technology (KIT)
Johannes V. Barth: Technische Universität München

Nature Communications, 2012, vol. 3, issue 1, 1-8

Abstract: Abstract The covalent linking of acetylenes presents an important route for the fabrication of novel carbon-based scaffolds and two-dimensional materials distinct from graphene. To date few attempts have been reported to implement this strategy at well-defined interfaces or monolayer templates. Here we demonstrate through real space direct visualization and manipulation in combination with X-ray photoelectron spectroscopy and density functional theory calculations the Ag surface-mediated terminal alkyne Csp−H bond activation and concomitant homo-coupling in a process formally reminiscent of the classical Glaser–Hay type reaction. The alkyne homo-coupling takes place on the Ag(111) noble metal surface in ultrahigh vacuum under soft conditions in the absence of conventionally used transition metal catalysts and with volatile H2 as the only by-product. With the employed multitopic ethynyl species, we demonstrate a hierarchic reaction pathway that affords discrete compounds or polymeric networks featuring a conjugated backbone. This presents a new approach towards on-surface covalent chemistry and the realization of two-dimensional carbon-rich or all-carbon polymers.

Date: 2012
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DOI: 10.1038/ncomms2291

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