Regensburg 2016 – scientific programme
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O: Fachverband Oberflächenphysik
O 37: Nanostructures at Surfaces III
O 37.5: Talk
Tuesday, March 8, 2016, 15:15–15:30, S054
Self-assembly and on-surface coupling of a carbonyl-bridged triphenylamine derivative — •Maximilian Ammon1, Zechao Yang1, Tim Sander1, Patrick Seitz1, Milan Kivala2, and Sabine Maier1 — 1Department of Physics, FAU Erlangen-Nürnberg, Germany — 2Department of Chemistry and Pharmacy, FAU Erlangen-Nürnberg, Germany
Carbonyl-bridged triphenylamines are versatile planar π-systems for the formation of self-assembled and covalent honeycomb networks. Here we present a low-temperature scanning tunneling microscopy (STM) study on the self-assembly of amino-functionalized carbonyl-bridged triphenylamine derivatives. On Au(111), we find hydrogen-bonded porous networks after evaporation at room temperature. The bonding motif is similar to the one expected in gas phase, which demonstrates a weak molecule-surface interaction. In contrast on Ag(111) the strong interaction between the carbonyl groups and the metal promotes metal-ligand bonded networks at room temperature. The bridging carbonyl groups are suitable for Schiff-base type coupling reactions, which proceed, compared to the Ullmann coupling, at lower temperatures and leave no reaction side products on the surface [1]. We will discuss results on the covalent coupling by post annealing on both surfaces.
[1] S. Weigelt, C. Busse, C. Bombis, et al., Angewandte Chemie 119, 9387-9390 (2007)