Dresden 2014 – wissenschaftliches Programm
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O: Fachverband Oberflächenphysik
O 62: Posters: Surface Reactions and Dynamics, Nanostructures
O 62.31: Poster
Mittwoch, 2. April 2014, 17:30–21:00, P1
Highly strained bicyclophanes on HOPG — Gabi Ohlendorf1, Christian W. Mahler1, •Stefan-S. Jester1, Gregor Schnakenburg2, Stefan Grimme3, and Sigurd Höger1 — 1Universität Bonn, Kekulé-Institut für Organische Chemie und Biochemie, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany — 2Universität Bonn, Institut für Anorganische Chemie, Gerhard-Domagk-Str. 1, 53121 Bonn, Germany — 3Universität Bonn, Mulliken Center for Theoretical Chemistry, Institut für Physikalische und Theoretische Chemie, Beringstrasse 4, 53115 Bonn, Germany
Architectures with aromatic units aligned perpendicularly to the graphite surface are rarely observed but may become of interest when functionalization towards the volume phase is desired. Recently, our group reported on a convenient synthesis of complex phenyl substituted p-phenylene oligomers without the need of common transition metal catalyzed cross-coupling reactions requiring complex protective group strategies. Based on these oligophenylenes, bicyclic components are obtained in very good yields. As confirmed by state-of-the-art DFT calculations, the molecules have a planar bicyclic unit with a perpendicular center which seems to be a promising structural unit to reach the purpose of three-dimensional growth on surfaces. Self-assembled monolayers of the bicyclophanes at the solid/liquid interface of 1-phenyloctane and HOPG are visualized by scanning tunneling microscopy (STM). [1] G. Ohlendorf, C. W. Mahler, S.-S. Jester, G. Schnakenburg, S. Grimme, S. Höger Angew. Chem. Int. Ed. 2013, 125, 12308.