Assigning the absolute configuration of single aliphatic molecules by visual inspection

作者：Ebeling Daniel^*; Sekutor Marina^*; Stiefermann Marvin; Tschakert Jalmar; Dahl Jeremy E P; Carlson Robert M K; Schirmeisen Andre^*; Schreiner Peter R^*

来源：Nature Communications, 2018, 9(1): 2420.

DOI：10.1038/s41467-018-04843-z

Deciphering absolute configuration of a single molecule by direct visual inspection is the next step in compound identification, with far-reaching implications for medicinal chemistry, pharmacology, and natural product synthesis. 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 a single, adsorbed [123] tetramantane molecule, the smallest chiral diamondoid. We differentiate between single enantiomers on Cu(111) by direct visual inspection, and furthermore identify molecular dimers and molecular clusters. The experimental results are confirmed by a computational study that allowed quantification of the corresponding intermolecular interactions. The unique toolset of absolute configuration determination combined with AFM tip manipulation opens a route for studying molecular nucleation, including chirality-driven assembly or reaction mechanisms.

• 出版日期2018-6-20