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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| Main Authors: | , , |
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| Format: | Article (Journal) |
| Language: | English |
| Published: |
2020
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| 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 |
| 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. |
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| 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 |