Exploration of pyrazine-embedded antiaromatic polycyclic hydrocarbons generated by solution and on-surface azomethine ylide homocoupling

Nanographenes, namely polycyclic aromatic hydrocarbons (PAHs) with nanoscale dimensions (>1 nm), are atomically precise cutouts from graphene. They represent prime models to enhance the scope of chemical and physical properties of graphene through structural modulation and functionalization. Defined nitrogen doping in nanographenes is particularly attractive due to its potential for increasing the number of π-electrons, with the possibility of introducing localized antiaromatic ring elements. Herein we present azomethine ylide homocoupling as a strategy to afford internally nitrogen-doped, non-planar PAH in solution and planar nanographene on surfaces, with central pyrazine rings. Localized antiaromaticity of…

• AV
  Alexander von Humboldt-Stiftung

  Award: H2020
• GF
  Graphene Flagship
• EC
  European Commission

  Awards: H2020-MSCA-IF-2014, H2020, 615233, H2020-MSCA, 664878, H2020-MSCA-IF
• DF
  Deutsche Forschungsgemeinschaft
• M
  Max-Planck-Gesellschaft
• H2
  Horizon 2020 Framework Programme

  Awards: H2020-MSCA, 615233, MSCA-IF-2014, 664878, H2020-MSCA-IF-2014
• ES
  European Social Fund