SurfaceScience21 – wissenschaftliches Programm
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O: Fachverband Oberflächenphysik
O 34: Poster Session III: Organic molecules on inorganic substrates: Adsorption and growth III
O 34.8: Poster
Dienstag, 2. März 2021, 10:30–12:30, P
Selective on-surface synthesis of oxygen heterocycles on metals
— •Andreas Dörr1, Nemanja Kocić1, Konstantin Amsharov2, and Sabine Maier1 — 1Department for Physics, Friedrich-Alexander-Universität Erlangen-Nürnberg — 2Institute for Chemistry, Martin-Luther-Universität Halle-Wittenberg
Heterocycles with nitrogen, oxygen, or sulfur atoms are the basic units to incorporate chemical functionalization into carbon scaffolds. For oxygen-doped nanographenes, furan and pyran - having five- and six-membered rings, respectively - are the most common ones. However, their on-surface synthesis via cyclomerization reactions remains elusive so far. Here we present a low-temperature scanning tunneling microscopy study to understand the on-surface synthesis of furan and pyran derivatives from ketone-functionalized precursors on metal surfaces. We use thermally induced CH-activation reactions to fuse two ketone-derivatives in either cis- and trans-configuration selectively. Finally, cyclomerization reactions towards furan and pyran moieties are observed after further annealing. These results are highly unexpected because ketone derivatives are mostly known to convert to cyclic trimers or tetramers in solution-based chemistry. On the surface, however, the strong interaction of the ketones with the metal surface and adatoms opens up new reaction pathways.