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Assigning the absolute configuration of single aliphatic molecules by visual inspection

Author

Listed:
  • Daniel Ebeling

    (Justus-Liebig University)

  • Marina Šekutor

    (Justus-Liebig University)

  • Marvin Stiefermann

    (Justus-Liebig University)

  • Jalmar Tschakert

    (Justus-Liebig University)

  • Jeremy E. P. Dahl

    (Stanford Institute for Materials and Energy Sciences)

  • Robert M. K. Carlson

    (Stanford Institute for Materials and Energy Sciences)

  • André Schirmeisen

    (Justus-Liebig University)

  • Peter R. Schreiner

    (Justus-Liebig University)

Abstract

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.

Suggested Citation

  • Daniel Ebeling & Marina Šekutor & Marvin Stiefermann & Jalmar Tschakert & Jeremy E. P. Dahl & Robert M. K. Carlson & André Schirmeisen & Peter R. Schreiner, 2018. "Assigning the absolute configuration of single aliphatic molecules by visual inspection," Nature Communications, Nature, vol. 9(1), pages 1-8, December.
    • Handle: RePEc:nat:natcom:v:9:y:2018:i:1:d:10.1038_s41467-018-04843-z
    DOI: 10.1038/s41467-018-04843-z
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    Cited by:

    1. Shigeki Kawai & Orlando J. Silveira & Lauri Kurki & Zhangyu Yuan & Tomohiko Nishiuchi & Takuya Kodama & Kewei Sun & Oscar Custance & Jose L. Lado & Takashi Kubo & Adam S. Foster, 2023. "Local probe-induced structural isomerization in a one-dimensional molecular array," Nature Communications, Nature, vol. 14(1), pages 1-7, December.

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