An isosteric triaza analogue of a polycyclic aromatic hydrocarbon monkey saddle

• Verfasst von: Kirschbaum, Tobias [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Mastalerz, Michael [VerfasserIn]
• Titel: An isosteric triaza analogue of a polycyclic aromatic hydrocarbon monkey saddle
• Verf.angabe: Tobias Kirschbaum, Frank Rominger, and Michael Mastalerz
• Jahr: 2020
• Umfang: 5 S.
• Fussnoten: First published: 15 June 2020 ; Gesehen am 03.11.2021
• Titel Quelle: Enthalten in: Chemistry - a European journal
• Ort Quelle: Weinheim : Wiley-VCH, 1995
• Jahr Quelle: 2020
• Band/Heft Quelle: 26(2020), 64, Seite 14560-14564
• ISSN Quelle: 1521-3765
• DOI: doi:10.1002/chem.202002826
• Datenträger: Online-Ressource
• Sprache: eng
• Sach-SW: azocine
• Sach-SW: chirality
• Sach-SW: monkey saddle
• Sach-SW: N-heteroarenes
• Sach-SW: negative curvature
• Sach-SW: polycyclic aromatic hydrocarbons
• K10plus-PPN: 1776043073
• K10plus-PPN:
  Universitätsbibliothek
• Lokale URL UB: Zum Volltext

Abstract

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.