A chiral polycyclic aromatic hydrocarbon monkey saddle

• Verfasst von: Kirschbaum, Tobias [VerfasserIn]
• Verfasst von: Rominger, Frank [VerfasserIn]
• Verfasst von: Mastalerz, Michael [VerfasserIn]
• Titel: A chiral polycyclic aromatic hydrocarbon monkey saddle
• Verf.angabe: Tobias Kirschbaum, Frank Rominger, and Michael Mastalerz
• Jahr: 2020
• Jahr des Originals: 2019
• Umfang: 5 S.
• Fussnoten: First published: 15 October 2019 ; Gesehen am 18.01.2021
• Titel Quelle: Enthalten in: Angewandte Chemie / International edition
• Ort Quelle: Weinheim : Wiley-VCH, 1962
• Jahr Quelle: 2020
• Band/Heft Quelle: 59(2020), 1, Seite 270-274
• ISSN Quelle: 1521-3773
• DOI: doi:10.1002/anie.201912213
• Datenträger: Online-Ressource
• Sprache: eng
• Bibliogr. Hinweis: Erscheint auch als : Kirschbaum, Tobias: A chiral polycyclic aromatic hydrocarbon monkey saddle. - 2020
• Sach-SW: chirality
• Sach-SW: cyclooctatetraene
• Sach-SW: monkey saddle
• Sach-SW: negative curvature
• Sach-SW: truxene
• K10plus-PPN: 1744877564
• K10plus-PPN:
  Universitätsbibliothek
• Lokale URL UB: Zum Volltext

Abstract

A contorted polycyclic aromatic hydrocarbon (PAH) in the shape of a monkey saddle has been synthesized in three steps from a readily available truxene precursor. The monkey saddle PAH is consisting of three five-, seven six-, and three eight-membered rings and has been unambiguously characterized by single-crystal X-ray diffraction. Owing to the three biaryl axes the monkey saddle PAH is inherently chiral. The inversion of the two enantiomeric structures into each other preferably occurs through a twisting of peripheral rings rather than by a fully planar intermediate, as has been calculated by DFT methods. Enantiomers were separated by chiral HPLC and inversion barriers determined by variable temperature circular dichroism spectroscopy, supporting the twisting mechanism.