Chiral Self‐Sorting of [2+3] Salicylimine Cage Compounds

• Published in: Angewandte Chemie International Edition Vol. 56; no. 5; pp. 1244 - 1248
• Main Authors: Beaudoin, Daniel, Rominger, Frank, Mastalerz, Michael
• Format: Journal Article
• Language: English
• Published: WEINHEIM Wiley 24.01.2017; Wiley Subscription Services, Inc
• Edition: International ed. in English
• Subjects: Cage compounds; Cages; Chemistry; Chemistry, Multidisciplinary; Entropy; macrocycles; microporous materials; Physical Sciences; Science & Technology; structure elucidation; thermodynamics; CRYSTALLIZATION; COMPLEXES; thermodynamics; MOLECULAR MARRIAGE; BORONIC ESTERS; DYNAMIC COMBINATORIAL LIBRARY; SHAPE; AMPLIFICATION; macrocycles; microporous materials; COVALENT ORGANIC CAGE; SYSTEMS; cage compounds; structure elucidation
• ISSN: 1433-7851; 1521-3773
• DOI: 10.1002/anie.201610782

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. Sorted out: 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 revealed that entropy favors narcissistic self‐sorting in solution, and selective social self‐sorting can be achieved by exploiting the difference in solubility between the homochiral and heterochiral cages.