Asymmetric azide‚Äźalkyne Huisgen cycloaddition on chiral metal surfaces


JSON Export

{
  "id": "762", 
  "metadata": {
    "title": "Asymmetric azide\u2010alkyne Huisgen cycloaddition on chiral metal surfaces", 
    "doi": "10.24435/materialscloud:tx-8g", 
    "license": "Creative Commons Attribution 4.0 International", 
    "keywords": [
      "SNSF", 
      "Azide\u2010alkyne Huisgen cycloaddition", 
      "asymmetric heterogeneous catalysis", 
      "on\u2010surface synthesis", 
      "ab-initio simulations", 
      "Experimental"
    ], 
    "contributors": [
      {
        "affiliations": [
          "Empa, Swiss Federal Laboratories for Materials Science and Technology, nanotech@surfaces Laboratory, 8600 D\u00fcbendorf, Switzerland", 
          "Institute of Physics, \u00c9cole Polytechnique F\u00e9d\u00e9rale de Lausanne, Laboratory of Nanostructures at Surfaces, 1015 Lausanne, Switzerland"
        ], 
        "familyname": "Stolz", 
        "email": "samuel.stolz@empa.ch", 
        "givennames": "Samuel"
      }, 
      {
        "affiliations": [
          "Empa, Swiss Federal Laboratories for Materials Science and Technology, Laboratory for Functional Polymers, 8600 D\u00fcbendorf, Switzerland"
        ], 
        "familyname": "Bauer", 
        "givennames": "Michael"
      }, 
      {
        "affiliations": [
          "Empa, Swiss Federal Laboratories for Materials Science and Technology, nanotech@surfaces Laboratory, 8600 D\u00fcbendorf, Switzerland"
        ], 
        "familyname": "Pignedoli", 
        "email": "carlo.pignedoli@empa.ch", 
        "givennames": "Carlo A."
      }, 
      {
        "affiliations": [
          "Empa, Swiss Federal Laboratories for Materials Science and Technology, nanotech@surfaces Laboratory, 8600 D\u00fcbendorf, Switzerland"
        ], 
        "familyname": "Krane", 
        "givennames": "Nils"
      }, 
      {
        "affiliations": [
          "Empa, Swiss Federal Laboratories for Materials Science and Technology, nanotech@surfaces Laboratory, 8600 D\u00fcbendorf, Switzerland"
        ], 
        "familyname": "Bommert", 
        "givennames": "Max"
      }, 
      {
        "affiliations": [
          "Empa, Swiss Federal Laboratories for Materials Science and Technology, nanotech@surfaces Laboratory, 8600 D\u00fcbendorf, Switzerland"
        ], 
        "familyname": "Turco", 
        "givennames": "Elia"
      }, 
      {
        "affiliations": [
          "Empa, Swiss Federal Laboratories for Materials Science and Technology, nanotech@surfaces Laboratory, 8600 D\u00fcbendorf, Switzerland"
        ], 
        "familyname": "Bassi", 
        "givennames": "Nicolo"
      }, 
      {
        "affiliations": [
          "Empa, Swiss Federal Laboratories for Materials Science and Technology, nanotech@surfaces Laboratory, 8600 D\u00fcbendorf, Switzerland"
        ], 
        "familyname": "Kinikar", 
        "givennames": "Amogh"
      }, 
      {
        "affiliations": [
          "Empa, Swiss Federal Laboratories for Materials Science and Technology, nanotech@surfaces Laboratory, 8600 D\u00fcbendorf, Switzerland"
        ], 
        "familyname": "Merino-D\u00ecez", 
        "givennames": "N\u00e9stor"
      }, 
      {
        "affiliations": [
          "Empa, Swiss Federal Laboratories for Materials Science and Technology, Laboratory for Functional Polymers, 8600 D\u00fcbendorf, Switzerland"
        ], 
        "familyname": "Hany", 
        "givennames": "Roland"
      }, 
      {
        "affiliations": [
          "Institute of Physics, \u00c9cole Polytechnique F\u00e9d\u00e9rale de Lausanne, Laboratory of Nanostructures at Surfaces, 1015 Lausanne, Switzerland"
        ], 
        "familyname": "Brune", 
        "givennames": "Harald"
      }, 
      {
        "affiliations": [
          "Empa, Swiss Federal Laboratories for Materials Science and Technology, nanotech@surfaces Laboratory, 8600 D\u00fcbendorf, Switzerland"
        ], 
        "familyname": "Gr\u00f6ning", 
        "givennames": "Oliver"
      }, 
      {
        "affiliations": [
          "Empa, Swiss Federal Laboratories for Materials Science and Technology, nanotech@surfaces Laboratory, 8600 D\u00fcbendorf, Switzerland"
        ], 
        "familyname": "Widmer", 
        "email": "roland.widmer@empa.ch", 
        "givennames": "Roland"
      }
    ], 
    "_files": [
      {
        "description": "zipped archive containing all files listed in ReadMe.yaml", 
        "checksum": "md5:1fce90f0bba89e78f23727517072e61a", 
        "size": 68557880, 
        "key": "data.tgz"
      }, 
      {
        "description": "ReadME file in yaml format listing the content of the record", 
        "checksum": "md5:16e41bdec13c407372941b63894499a9", 
        "size": 40227, 
        "key": "ReadMe.yaml"
      }, 
      {
        "description": "archive AiiDA file containing all nodes and their provenance for the calculations discussed in the manuscript", 
        "checksum": "md5:249e59b9b67b08e83bca70c7c2883c68", 
        "size": 294974390, 
        "key": "pdga.aiida"
      }
    ], 
    "references": [
      {
        "type": "Journal reference", 
        "citation": "S. Stolz, M. Bauer, C. A. Pignedoli, N. Krane, M. Bommert, E. Turco, N. Bassi, A. Kinikar, N. Merino-D\u00ecez, R. Hany, H. Brune, O. Gr\u00f6ning, R. Widmer, Commun. Chem., in press (2021)", 
        "comment": "Manuscript where the results are discussed.", 
        "url": ""
      }
    ], 
    "conceptrecid": "761", 
    "version": 1, 
    "edited_by": 100, 
    "id": "762", 
    "owner": 243, 
    "mcid": "2021.38", 
    "is_last": true, 
    "status": "published", 
    "description": "The record contains the data supporting our recent findings on asymmetric azide-alkyne Huisgen cycloaddition on chiral metal surfaces:\nAchieving 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\u2010defined, and chiral intermetallic PdGa{111} surfaces as catalytic substrates. We demonstrate the impact of chirality transfer and ensemble effect for the thermally activated azide\u2010alkyne Huisgen cycloaddition between 3\u2010(4\u2010azidophenyl)propionic acid and 9\u2010ethynylphenanthrene on these threefold symmetric intermetallic surfaces under ultrahigh vacuum conditions. Specifically, we encounter a dominating ensemble effect for this reaction as on the Pd3\u2010terminated PdGa{111} surfaces no stable heterocoupled structures are created, while on the Pd1\u2010terminated 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\u2010terminated PdGa{111} surfaces. Our results evidence a determinant ensemble effect and the immense potential of PdGa as asymmetric heterogeneous catalyst.", 
    "license_addendum": null, 
    "_oai": {
      "id": "oai:materialscloud.org:762"
    }, 
    "publication_date": "Mar 02, 2021, 14:37:37"
  }, 
  "revision": 5, 
  "updated": "2021-03-02T13:37:37.701688+00:00", 
  "created": "2021-03-02T11:11:33.815391+00:00"
}