On-surface polyarylene synthesis by cycloaromatization of isopropyl substituents


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{
  "metadata": {
    "is_last": true, 
    "publication_date": "Jan 25, 2022, 11:38:02", 
    "edited_by": 576, 
    "version": 1, 
    "license": "Creative Commons Attribution 4.0 International", 
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      "ab initio", 
      "on surface synthesis", 
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    "contributors": [
      {
        "givennames": "Amogh", 
        "email": "amogh.kinikar@empa.ch", 
        "familyname": "Kinikar", 
        "affiliations": [
          "Empa, Swiss Federal Laboratories for Materials Science and Technology, 8600 D\u00fcbendorf (Switzerland)"
        ]
      }, 
      {
        "givennames": "Marco", 
        "familyname": "Di Giovannantonio", 
        "affiliations": [
          "Empa, Swiss Federal Laboratories for Materials Science and Technology, 8600 D\u00fcbendorf (Switzerland)"
        ]
      }, 
      {
        "givennames": "Jos\u00e9", 
        "familyname": "I. Urgel", 
        "affiliations": [
          "Empa, Swiss Federal Laboratories for Materials Science and Technology, 8600 D\u00fcbendorf (Switzerland)"
        ]
      }, 
      {
        "givennames": "Kristjan", 
        "familyname": "Eimre", 
        "affiliations": [
          "Empa, Swiss Federal Laboratories for Materials Science and Technology, 8600 D\u00fcbendorf (Switzerland)"
        ]
      }, 
      {
        "givennames": "Zijie", 
        "familyname": "Qiu", 
        "affiliations": [
          "Max Planck Institute for Polymer Research, 55128 Mainz (Germany)"
        ]
      }, 
      {
        "givennames": "Yanwei", 
        "familyname": "Gu", 
        "affiliations": [
          "Max Planck Institute for Polymer Research, 55128 Mainz (Germany)"
        ]
      }, 
      {
        "givennames": "Enquan", 
        "familyname": "Jin", 
        "affiliations": [
          "Max Planck Institute for Polymer Research, 55128 Mainz (Germany)"
        ]
      }, 
      {
        "givennames": "Akimitsu", 
        "familyname": "Narita", 
        "affiliations": [
          "Max Planck Institute for Polymer Research, 55128 Mainz (Germany)"
        ]
      }, 
      {
        "givennames": "Xiao-Ye", 
        "familyname": "Wang", 
        "affiliations": [
          "Max Planck Institute for Polymer Research, 55128 Mainz (Germany)"
        ]
      }, 
      {
        "givennames": "Klaus", 
        "familyname": "M\u00fcllen", 
        "affiliations": [
          "Max Planck Institute for Polymer Research, 55128 Mainz (Germany)", 
          "Institute of Physical Chemistry, Johannes Gutenberg, Universit\u00e4t Mainz, 55128 Mainz (Germany)"
        ]
      }, 
      {
        "givennames": "Pascal", 
        "familyname": "Ruffieux", 
        "affiliations": [
          "Empa, Swiss Federal Laboratories for Materials Science and Technology, 8600 D\u00fcbendorf (Switzerland)"
        ]
      }, 
      {
        "givennames": "Carlo Antonio", 
        "email": "carlo.pignedoli@empa.ch", 
        "familyname": "Pignedoli", 
        "affiliations": [
          "Empa, Swiss Federal Laboratories for Materials Science and Technology, 8600 D\u00fcbendorf (Switzerland)"
        ]
      }, 
      {
        "givennames": "Roman", 
        "email": "roman.fasel@empa.ch", 
        "familyname": "Fasel", 
        "affiliations": [
          "Empa, Swiss Federal Laboratories for Materials Science and Technology, 8600 D\u00fcbendorf (Switzerland)", 
          "Department of Chemistry, Biochemistry and Pharmaceutical Sciences, University of Bern, 3012 Bern (Switzerland)"
        ]
      }
    ], 
    "status": "published", 
    "doi": "10.24435/materialscloud:yy-sc", 
    "title": "On-surface polyarylene synthesis by cycloaromatization of isopropyl substituents", 
    "id": "1190", 
    "description": "In this record we provide the data to support our recent finding on surface catalyzed cycloaromatization. Immobilization of organic building blocks on metal surfaces and their coupling via thermally induced C-C bond formations are developing as an important addition to the toolbox of organic and polymer synthesis. Additional advantages of this technique are the in situ monitoring of the reaction by scanning probe methods and the accessibility of insoluble and reactive carbon nanostructures. The diversity of conceivable products, however, sensitively depends on the number of available on-surface reactions. In the manuscript where the results are discussed, we introduce an unprecedented example, the intermolecular oxidative coupling of isopropyl substituents of arenes. With a new phenylene ring being formed, this [3+3] dimerization can be regarded as a formal cycloaromatization. The synthetic value of this novel reaction is proven by the synthesis of polyarylenes and co-polyarylenes, which we demonstrate by synthesizing poly(2,7-pyrenylene-1,4-phenylene). Scanning tunneling microscopy and non-contact atomic force microscopy studies complemented by density functional theory calculations are employed to obtain mechanistic insights into the title reaction.", 
    "owner": 614, 
    "_oai": {
      "id": "oai:materialscloud.org:1190"
    }, 
    "conceptrecid": "1189", 
    "references": [
      {
        "doi": "10.1038/s44160-022-00032-5", 
        "comment": "Paper where the data is discussed", 
        "citation": "A. Kinikar, M. Di Giovannantonio, J. I. Urgel, K. Eimre, Z. Qiu, Y. Gu, E. Jin, A. Narita, X. Wang, K. M\u00fcllen, P. Ruffieux, C. A. Pignedoli, and R. Fasel, Nature Synthesis (2022)", 
        "type": "Journal reference"
      }
    ]
  }, 
  "updated": "2022-01-25T10:38:02.702547+00:00", 
  "revision": 5, 
  "id": "1190", 
  "created": "2021-12-21T09:54:51.816608+00:00"
}