Chiral Self-Sorting of [2+3] Salicylimine Cage Compounds
Daniel Beaudoin1, Frank Rominger1, Michael Mastalerz1
1Organisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, 69120, Heidelberg, Germany.
Abstract:
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.
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