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Chiral self-sorting of giant cubic [8+12] Salicylimine cage compounds

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Chiral self-sorting is intricately connected to the complicated chiral processes observed in nature and no artificial systems of comparably complexity have been generated by chemists. However, only a few examples of purely organic molecules have been reported so far, where the self-sorting process c...

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Main Authors: Wagner, Philippe (Author) , Rominger, Frank (Author) , Zhang, Wen-Shan (Author) , Gross, Jürgen H. (Author) , Elbert, Sven (Author) , Schröder, Rasmus R. (Author) , Mastalerz, Michael (Author)
Format: Article (Journal)
Language:English
Published: 2021
In: Angewandte Chemie
Year: 2021, Volume: 133, Issue: 16, Pages: 8978-8986
ISSN:1521-3757
DOI:10.1002/ange.202016592
Online Access:Verlag, kostenfrei, Volltext: https://doi.org/10.1002/ange.202016592
Verlag, kostenfrei, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/ange.202016592
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Author Notes:Philippe Wagner, Frank Rominger, Wen-Shan Zhang, Jürgen H. Gross, Sven M. Elbert, Rasmus R. Schröder, and Michael Mastalerz
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Summary:Chiral self-sorting is intricately connected to the complicated chiral processes observed in nature and no artificial systems of comparably complexity have been generated by chemists. However, only a few examples of purely organic molecules have been reported so far, where the self-sorting process could be controlled. Herein, we describe the chiral self-sorting of large cubic [8+12] salicylimine cage compounds based on a chiral TBTQ precursor. Out of 23 possible cage isomers only the enantiopure and a meso cage were observed to be formed, which have been unambiguously characterized by single crystal X-ray diffraction. Furthermore, by careful choice of solvent the formation of meso cage could be controlled. With internal diameters of din=3.3-3.5 nm these cages are among the largest organic cage compounds characterized and show very high specific surface areas up to approx. 1500 m2 g−1 after desolvation.
Item Description:Gesehen am 21.04.2023
Physical Description:Online Resource
ISSN:1521-3757
DOI:10.1002/ange.202016592

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