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@ARTICLE{Klein:861478,
      author       = {Klein, Benedikt P. and van der Heijden, Nadine J. and
                      Kachel, Stefan R. and Franke, Markus and Krug, Claudio K.
                      and Greulich, Katharina K. and Ruppenthal, Lukas and
                      Müller, Philipp and Rosenow, Phil and Parhizkarmazinani,
                      Shayan and Posseik, Francois and Schmid, Martin and
                      Hieringer, Wolfgang and Maurer, Reinhard J. and Tonner, Ralf
                      and Kumpf, Christian and Swart, Ingmar and Gottfried, J.
                      Michael},
      title        = {{M}olecular {T}opology and the {S}urface {C}hemical {B}ond:
                      {A}lternant {V}ersus {N}onalternant {A}romatic {S}ystems as
                      {F}unctional {S}tructural {E}lements},
      journal      = {Physical review / X Expanding access X},
      volume       = {9},
      number       = {1},
      issn         = {2160-3308},
      address      = {College Park, Md.},
      publisher    = {APS},
      reportid     = {FZJ-2019-01943},
      pages        = {011030},
      year         = {2019},
      abstract     = {The interaction of carbon-based aromatic molecules and
                      nanostructures with metals can strongly depend on the
                      topology of their π-electron systems. This is shown with a
                      model system using the isomers azulene, which has a
                      nonalternant π system with a 5-7 ring structure, and
                      naphthalene, which has an alternant π system with a 6-6
                      ring structure. We found that azulene can interact much more
                      strongly with metal surfaces. On copper (111), its
                      zero-coverage desorption energy is 1.86 eV, compared to 1.07
                      eV for naphthalene. The different bond strengths are
                      reflected in the adsorption heights, which are 2.30 Å for
                      azulene and 3.04 Å for naphthalene, as measured by the
                      normal incidence x-ray standing wave technique. These
                      differences in the surface chemical bond are related to the
                      electronic structure of the molecular π systems. Azulene
                      has a low-lying LUMO that is close to the Fermi energy of Cu
                      and strongly hybridizes with electronic states of the
                      surface, as is shown by photoemission, near-edge x-ray
                      absorption fine-structure, and scanning tunneling microscopy
                      data in combination with theoretical analysis. According to
                      density functional theory calculations, electron donation
                      from the surface into the molecular LUMO leads to negative
                      charging and deformation of the adsorbed azulene. Noncontact
                      atomic force microscopy confirms the deformation, while
                      Kelvin probe force microscopy maps show that adsorbed
                      azulene partially retains its in-plane dipole. In contrast,
                      naphthalene experiences only minor adsorption-induced
                      changes of its electronic and geometric structure. Our
                      results indicate that the electronic properties of
                      metal-organic interfaces, as they occur in organic
                      (opto)electronic devices, can be tuned through modifications
                      of the π topology of the molecular organic semiconductor,
                      especially by introducing 5-7 ring pairs as functional
                      structural elements.},
      cin          = {PGI-3},
      ddc          = {530},
      cid          = {I:(DE-Juel1)PGI-3-20110106},
      pnm          = {143 - Controlling Configuration-Based Phenomena (POF3-143)
                      / DFG project 396769409 - Grundlagen der
                      Photoemissionstomographie},
      pid          = {G:(DE-HGF)POF3-143 / G:(GEPRIS)396769409},
      typ          = {PUB:(DE-HGF)16},
      UT           = {WOS:000458822800001},
      doi          = {10.1103/PhysRevX.9.011030},
      url          = {https://juser.fz-juelich.de/record/861478},
}