Chiral self-sorting of (2+3) salicylimine cage compounds

An inherently chiral C3-symmetric triaminotribenzotriquinacene was condensed in racemic and enantiomerically pure form with a bis(salicylaldehyde) to form [2+3] salicylimine cage compounds. Investigations on the chiral self-sorting revealed that while entropy favors narcissistic self-sorting in solu...

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Hauptverfasser: Beaudoin, Daniel (VerfasserIn) , Rominger, Frank (VerfasserIn) , Mastalerz, Michael (VerfasserIn)
Dokumenttyp: Article (Journal)
Sprache:Englisch
Veröffentlicht: 2017
In: Angewandte Chemie. International edition
Year: 2016, Jahrgang: 56, Heft: 5, Pages: 1244-1248
ISSN:1521-3773
DOI:10.1002/anie.201610782
Online-Zugang:Verlag, Volltext: http://dx.doi.org/10.1002/anie.201610782
Verlag, Volltext: https://onlinelibrary.wiley.com/doi/abs/10.1002/anie.201610782
Volltext
Verfasserangaben:Daniel Beaudoin, Frank Rominger, and Michael Mastalerz
Beschreibung
Zusammenfassung:An inherently chiral C3-symmetric triaminotribenzotriquinacene was condensed in racemic and enantiomerically pure form with a bis(salicylaldehyde) to form [2+3] salicylimine cage compounds. Investigations on the chiral self-sorting revealed that while entropy favors narcissistic self-sorting in solution, selective social self-sorting can be achieved by exploiting the difference in solubility between the homochiral and heterochiral cages. Gas sorption measurements further showed that seemingly small structural differences can have a significant impact on the surface area of microporous covalent cage compounds.
Beschreibung:First published: 22 December 2016
Gesehen am 13.09.2018
Beschreibung:Online Resource
ISSN:1521-3773
DOI:10.1002/anie.201610782