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A chiral polycyclic aromatic hydrocarbon monkey saddle

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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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Bibliographische Detailangaben
Hauptverfasser: Kirschbaum, Tobias (VerfasserIn) , Rominger, Frank (VerfasserIn) , Mastalerz, Michael (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 2020
In: Angewandte Chemie. International edition
Year: 2019, Jahrgang: 59, Heft: 1, Pages: 270-274
ISSN:1521-3773
DOI:https://doi.org/10.1002/anie.201912213
Online-Zugang: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
Volltext
Verfasserangaben:Tobias Kirschbaum, Frank Rominger, and Michael Mastalerz

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520 |a 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. 
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