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O: Fachverband Oberflächenphysik

O 64: Focus Session: Molecular Nanostructures on surfaces - New Concepts towards Complex Architectures IV

O 64.2: Vortrag

Mittwoch, 14. März 2018, 15:15–15:30, MA 004

Assigning the absolute configuration of chiral aliphatic compounds by direct visual inspection of individual molecules — Daniel Ebeling¹, Marina Sekutor², Marvin Stiefermann¹, Jalmar Tschakert¹, Jeremy Dahl³, Robert Carlson³, Peter Schreiner², and •Andre Schirmeisen¹ — ¹Institute of Applied Physics, Justus-Liebig University Giessen, Germany — ²Institute of Organic Chemistry, Justus-Liebig University Giessen, Germany — ³cStanford Institute for Materials and Energy Sciences, Stanford, USA

Deciphering the absolute configuration of a single molecule by direct visual inspection is the next step in direct compound identification, with far-reaching implications for medicinal chemistry, pharmacology, and natural product synthesis. Here we demonstrate the feasibility of this approach utilizing low temperature atomic force microscopy (AFM) with a CO-functionalized tip to determine the absolute configuration and orientation of single adsorbed [123]tetramantane molecule, the smallest chiral diamondoid. We differentiate between single enantiomers on a Cu(111) surface by direct visual inspection with atomic precision, and furthermore identify molecular dimers and small molecular clusters. The experimental results were also confirmed by a computational study that additionally allowed quantification of the corresponding intermolecular interactions. The unique toolset of absolute configuration determination combined with AFM tip manipulation now opens the route for unprecedented molecular nucleation studies, including chirality driven assembly or reaction mechanisms.