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Chiral Self‐Sorting of [2+3] Salicylimine Cage Compounds
Author(s) -
Beaudoin Daniel,
Rominger Frank,
Mastalerz Michael
Publication year - 2017
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201610782
Subject(s) - cage , chemistry , salicylaldehyde , sorting , entropy (arrow of time) , self assembly , cage effect , computational chemistry , stereochemistry , organic chemistry , thermodynamics , mathematics , combinatorics , physics , molecule , algorithm , schiff base
An inherently chiral C 3 ‐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.