Negatively Curved Warped Nanographene Self-Assembled on Metal Surfaces

  • José I. Urgel
    Empa, Swiss Federal Laboratories for Materials Science and Technology, 8600 Dübendorf, Switzerland
  • Marco Di Giovannantonio
    Empa, Swiss Federal Laboratories for Materials Science and Technology, 8600 Dübendorf, Switzerland
  • Pascal Ruffieux
    Empa, Swiss Federal Laboratories for Materials Science and Technology, 8600 Dübendorf, Switzerland
  • Lawrence T. Scott
    Merkert Chemistry Center, Boston College, Chestnut Hill, Massachusetts 02467-3860, United States
  • Carlo A. Pignedoli
    Empa, Swiss Federal Laboratories for Materials Science and Technology, 8600 Dübendorf, Switzerland
  • Roman Fasel
    Empa, Swiss Federal Laboratories for Materials Science and Technology, 8600 Dübendorf, Switzerland

書誌事項

公開日
2019-07-24
資源種別
journal article
権利情報
  • https://doi.org/10.15223/policy-029
  • https://doi.org/10.15223/policy-037
  • https://doi.org/10.15223/policy-045
DOI
  • 10.1021/jacs.9b05501
  • 10.7892/boris.141655
公開者
American Chemical Society (ACS)

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説明

We report the investigation of a conjugated polycyclic hydrocarbon containing multiple nonbenzenoid rings and exhibiting negative curvature-the warped nanographene C80H30-adsorbed on several noble metal surfaces in an ultrahigh vacuum environment. From a detailed analysis of the molecular self-assembly at different molecular coverages via scanning tunneling microscopy and spectroscopy measurements in combination with theoretical modeling, the nature of the intermolecular interactions is unraveled. For high molecular coverages on Cu(111), the formation of homochiral porous networks is observed, which is rationalized by (i) intermolecular π-π interactions between neighboring C80H30 molecules that promote the formation of molecular dimers and (ii) enantioselective intermolecular CH···π interactions between the dimers. Such interactions are also observed after deposition of C80H30 molecules on Au(111) and Ag(111) substrates. Our results provide perspectives for the on-surface study of negatively curved nanographenes which open new avenues to the design of novel and functional chiral structures with potential use in the field of organic optoelectronics.

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