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O: Fachverband Oberflächenphysik
O 25: Poster: Metal Substrates
O 25.4: Poster
Monday, March 27, 2023, 18:00–20:00, P2/EG
Single-molecule study of Heck coupling on a Cu(111) surface — •Donato Civita1, Friedrich Esch2, and Leonhard Grill1 — 1Department of Physical Chemistry, University of Graz, Austria — 2Faculty of Chemistry, TU München, Germany
The interaction of organic molecules with metallic structures is particularly important in heterogeneous catalysis where metallic particles or surfaces help to overcome energy barriers of chemical reactions. This concept is specifically important for Heck cross-coupling, which relies on a palladium catalyst to form a carbon-carbon bond between two different reagents. Model heterogeneous catalysis reactions can be investigated by scanning tunneling microscopy (STM) on metal single crystals. The role of active sites could be determined [1,2], and Heck coupling could be induced thermally [3].
We studied the cross coupling between vinyl-naphthalene (VN) and different halogenated molecules on a Cu(111) surface by STM at low temperatures (7 K). We investigated the bond of the de-halogenated molecules to different atomic structures of the copper surface as well as the thermally induced cross coupling reaction. By the statistical analysis of the products, and STM manipulation of a single metal-organic intermediate we obtain insight into the catalytic activity of the copper surface, and the dependence on the surface morphology.
[1] Hla, S.-W., et al., Phys. Rev. Lett., 85(13) (2000)
[2] Zambelli, T., et al., Science, 273 (1996)
[3] Shi, K.-J., et al., Organic Letters, 19(11) (2017)