Samuel Stolz^1,2*, Michael Bauer³, Carlo A. Pignedoli^1*, Nils Krane¹, Max Bommert¹, Elia Turco¹, Nicolo Bassi¹, Amogh Kinikar¹, Néstor Merino-Dìez¹, Roland Hany³, Harald Brune², Oliver Gröning¹, Roland Widmer^1*

1 Empa, Swiss Federal Laboratories for Materials Science and Technology, nanotech@surfaces Laboratory, 8600 Dübendorf, Switzerland

2 Institute of Physics, École Polytechnique Fédérale de Lausanne, Laboratory of Nanostructures at Surfaces, 1015 Lausanne, Switzerland

3 Empa, Swiss Federal Laboratories for Materials Science and Technology, Laboratory for Functional Polymers, 8600 Dübendorf, Switzerland

* Corresponding authors emails: samuel.stolz@empa.ch, carlo.pignedoli@empa.ch, roland.widmer@empa.ch

DOI10.24435/materialscloud:tx-8g [version v1]

Publication date: Mar 02, 2021

How to cite this record

Samuel Stolz, Michael Bauer, Carlo A. Pignedoli, Nils Krane, Max Bommert, Elia Turco, Nicolo Bassi, Amogh Kinikar, Néstor Merino-Dìez, Roland Hany, Harald Brune, Oliver Gröning, Roland Widmer, Asymmetric azide‐alkyne Huisgen cycloaddition on chiral metal surfaces, Materials Cloud Archive 2021.38 (2021), https://doi.org/10.24435/materialscloud:tx-8g

Description

The record contains the data supporting our recent findings on asymmetric azide-alkyne Huisgen cycloaddition on chiral metal surfaces: Achieving fundamental understanding of enantioselective heterogeneous synthesis is marred by the permanent presence of multitudinous arrangements of catalytically active sites in real catalysts. We address this issue by using structurally comparatively simple, well‐defined, and chiral intermetallic PdGa{111} surfaces as catalytic substrates. We demonstrate the impact of chirality transfer and ensemble effect for the thermally activated azide‐alkyne Huisgen cycloaddition between 3‐(4‐azidophenyl)propionic acid and 9‐ethynylphenanthrene on these threefold symmetric intermetallic surfaces under ultrahigh vacuum conditions. Specifically, we encounter a dominating ensemble effect for this reaction as on the Pd3‐terminated PdGa{111} surfaces no stable heterocoupled structures are created, while on the Pd1‐terminated PdGa{111} surfaces, the cycloaddition proceeds regioselectively. Moreover, we observe chirality transfer from the substrate to the reaction products, as they are formed enantioselectively on the Pd1‐terminated PdGa{111} surfaces. Our results evidence a determinant ensemble effect and the immense potential of PdGa as asymmetric heterogeneous catalyst.

Materials Cloud sections using this data

Files

File name	Size	Description
data.tgz MD5md5:1fce90f0bba89e78f23727517072e61a	65.4 MiB	zipped archive containing all files listed in ReadMe.yaml
ReadMe.yaml MD5md5:16e41bdec13c407372941b63894499a9	39.3 KiB	ReadME file in yaml format listing the content of the record
pdga.aiida MD5md5:249e59b9b67b08e83bca70c7c2883c68 Open this AiiDA archive on renkulab.io (https://renkulab.io/)	281.3 MiB	archive AiiDA file containing all nodes and their provenance for the calculations discussed in the manuscript

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.

External references

Keywords

SNSF Azide‐alkyne Huisgen cycloaddition asymmetric heterogeneous catalysis on‐surface synthesis ab-initio simulations Experimental