• Media type: E-Article
  • Title: An isosteric triaza analogue of a polycyclic aromatic hydrocarbon monkey saddle
  • Contributor: Kirschbaum, Tobias [Author]; Rominger, Frank [Author]; Mastalerz, Michael [Author]
  • Published: 2020
  • Published in: Chemistry - a European journal ; 26(2020), 64, Seite 14560-14564
  • Language: English
  • DOI: 10.1002/chem.202002826
  • Identifier:
  • Keywords: azocine ; chirality ; monkey saddle ; N-heteroarenes ; negative curvature ; polycyclic aromatic hydrocarbons
  • Origination:
  • Footnote: First published: 15 June 2020
  • Description: Since a few years, the interest in negatively-curved fused polycyclic aromatic hydrocarbons (PAHs) has significantly increased. Recently, the first chiral negatively-curved PAH with the topology of a monkey saddle was introduced. Herein the synthesis of its triaza congener is reported. The influence of this CH↔N exchange on photophysical and electrochemical properties is studied as well as the isomerization process of the enantiomers. The aza analogue has a significantly higher inversion barrier, which makes it easier to handle at room temperature. All experimental results are underpinned by theoretical DFT calculations.
  • Access State: Open Access