×

Recommended by

Indexed by

Asymmetric elimination reaction on chiral metal surfaces

Samuel Stolz1,2, Martina Danese1, Marco Di Giovannantonio1, José I. Urgel1, Qiang Sun1, Amogh Kinikar1, Max Bommert1, Shantanu Mishra1, Harald Brune2, Oliver Gröning1, Daniele Passerone1, Roland Widmer1*

1 Empa, Swiss Federal Laboratories for Materials Science and Technology, CH-8600 Dübendorf, Switzerland

2 Institute of Physics, École Polytechnique Fédérale de Lausanne, CH-1015 Lausanne, Switzerland

* Corresponding authors emails: roland.widmer@empa.ch
DOI10.24435/materialscloud:pm-8p [version v1]

Publication date: Oct 11, 2021

How to cite this record

Samuel Stolz, Martina Danese, Marco Di Giovannantonio, José I. Urgel, Qiang Sun, Amogh Kinikar, Max Bommert, Shantanu Mishra, Harald Brune, Oliver Gröning, Daniele Passerone, Roland Widmer, Asymmetric elimination reaction on chiral metal surfaces, Materials Cloud Archive 2021.162 (2021), doi: 10.24435/materialscloud:pm-8p.

Description

The production of enantiopure materials and molecules is of uttermost relevance in research and industry in numerous contexts, ranging from non-linear optics to asymmetric synthesis. In the context of the latter, we have investigated dehalogenation, which is an essential reaction step for a broad class of chemical reactions. Specifically, dehalogenation of prochiral 5-bromo-7-methylbenz(a)anthracene (BMA) on prototypical, chiral, intermetallic PdGa{111} surfaces under ultrahigh vacuum conditions. Enantioselective halogen elimination is demonstrated by combining temperature-programmed x-ray photoelectron spectroscopy, scanning probe microscopy, and density functional theory. On the PdGa{111} surfaces, the difference in debromination temperatures for the two BMA surface enantiomers amounts up to unprecedented 46 K. The significant dependence of the dehalogenation temperature of the BMA surface enantiomers on the atomic termination of the PdGa{111} surfaces, implies that the ensemble effect is pronounced in this reaction step. These findings evidence enantiospecific control and hence promote intrinsically chiral crystals for asymmetric on-surface synthesis. The record contains input files to reproduce the calculations discussed in the manuscript and the raw data of the experimental images discussed.

Materials Cloud sections using this data

No Explore or Discover sections associated with this archive record.

Files

File name Size Description
ReadMe.yaml
MD5md5:6cd9b757abb091bd98537880750b222a
27.3 KiB README file in yaml format detailing the content of the record
data.tgz
MD5md5:375dae1b977df5f7b3a34ee46015fa1a
256.6 MiB tar file containing all data
debromination.aiida
MD5md5:a6252cd0acc0dad155c6df8face98a82
662.6 MiB Archive of AiiDA nodes for the calculations of geometry optimization (brominated molecules) desribed in the manuscript and SI.

License

Files and data are licensed under the terms of the following license: Creative Commons Attribution 4.0 International.
Metadata, except for email addresses, are licensed under the Creative Commons Attribution Share-Alike 4.0 International license.

Keywords

ab initio scanning probe microscopy enantioselectivity MARVEL/DD3 SNSF

Version history:

2021.162 (version v1) [This version] Oct 11, 2021 DOI10.24435/materialscloud:pm-8p