A chiral polycyclic aromatic hydrocarbon monkey saddle

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...

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Bibliographic Details
Main Authors: Kirschbaum, Tobias (Author) , Rominger, Frank (Author) , Mastalerz, Michael (Author)
Format: Article (Journal)
Language:English
Published: 2020
In: Angewandte Chemie. International edition
Year: 2019, Volume: 59, Issue: 1, Pages: 270-274
ISSN:1521-3773
DOI:https://doi.org/10.1002/anie.201912213
Online Access:Verlag, lizenzpflichtig, Volltext: https://doi.org/https://doi.org/10.1002/anie.201912213
Verlag, lizenzpflichtig, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201912213
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Author Notes:Tobias Kirschbaum, Frank Rominger, and Michael Mastalerz
Description
Summary: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.
Item Description:First published: 15 October 2019
Gesehen am 18.01.2021
Physical Description:Online Resource
ISSN:1521-3773
DOI:https://doi.org/10.1002/anie.201912213