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Chirality‐Assisted Synthesis of a Very Large Octameric Hydrogen‐Bonded Capsule
Author(s) -
Beaudoin Daniel,
Rominger Frank,
Mastalerz Michael
Publication year - 2016
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.201609073
Subject(s) - enantiopure drug , capsule , chirality (physics) , hydrogen , block (permutation group theory) , cube (algebra) , materials science , ion , crystallography , chemistry , stereochemistry , geometry , mathematics , organic chemistry , physics , enantioselective synthesis , catalysis , geology , chiral symmetry breaking , quantum mechanics , quark , nambu–jona lasinio model , paleontology
The strategy of chirality‐assisted synthesis, which makes use of enantiomerically pure building blocks that are designed to associate in a single geometric orientation, was applied to synthesize an octameric hydrogen‐bonded capsule with a cavity volume of 2300 Å 3 . This cube‐shaped capsule forms even host–guest complexes with tetraalkylammonium ions, and accommodates the large tetrahexadecylammonium cation in its cavity. The use of an enantiopure building block was shown to be highly beneficial for capsule formation, whereas its racemate also generates a large amount of ill‐defined aggregates in solution and crystallizes as a hydrogen‐bonded network.