Dresden 2020 – scientific programme

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O: Fachverband Oberflächenphysik

O 87: Poster Session - Nanostructures at Surfaces: 1D and 2D Structures and Networks

O 87.6: Poster

Wednesday, March 18, 2020, 18:15–20:00, P2/1OG

Isomorphic packing of carboxylic acid terminated arylene-alkynylenes and monodisperse oligomers on graphite — •David A. Hofmeister, Lucas Rothe, Tristan J. Keller, Sigurd Höger, and Stefan-S. Jester — Kekulé-Institut für Organische Chemie und Biochemie, Rheinische Friedrich-Wilhelms-Universität Bonn, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany.

Arylene-alkynylenes form supramolecular nanopatterns at the solid/liquid interface of graphite (HOPG), that are imaged by scanning tunneling microscopy with submolecular resolution. The structure of the two-dimensional (2D) crystals depends on the exact geometry of the shape-persistent backbones, the substitution with functional groups that mediate the interaction of such species, and (intermolecularly interdigitating) alkoxy side chains. Here, we report on (i) arylene-alkynylenes that carry OC16H33 side chains and carboxylic end groups and are obtained in a stepwise synthesis, and (ii) monodisperse oligomers of alike systems obtained by oxidative Glaser coupling of acetylene-terminated precursors and subsequent separation by recycling gel permeation chromatography. Both species form isomorphous 2D packings, which is drawn back to alike spatial requirements of (i) carboxylic acid dimers that form after adsorption and (ii) butadiynylene units.