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Novel Capsular Aggregates from Flexible Tripodal Triureas with C s Symmetry
Author(s) -
Alajarin Mateo,
Orenes RaulAngel,
Howard Judith A. K.,
Spencer Elinor C.,
Steed Jonathan W.,
Pastor Aurelia
Publication year - 2012
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.201102246
Subject(s) - tris , chemistry , structural isomer , symmetry (geometry) , self assembly , solid state , crystallography , stereochemistry , polymer chemistry , organic chemistry , biochemistry , geometry , mathematics
Tris(2‐ and 3‐ureidobenzyl)amines with C s symmetry self‐assemble in solution forming mixtures of regioisomeric capsular aggregates, one of which is chiral and the other centrosymmetric. Under certain conditions, a predominance of the centrosymmetric regioisomer is found before equilibrium, that is, a mixture close to the statistical ratio of the two species is reached. In the solid state, there is a preference for the centrosymmetric capsules. Molecular models of both regioisomeric aggregates have been built and analyzed for comparison. Guests inside capsules formed by self‐assembly of desymmetrized tris(3‐ureidobenzyl)amines feel different magnetic environments, depending on whether they are inside a chiral or an achiral regioisomeric container. Of special significance are the experiments with a more flexible triurea endowed with an ureidopropylic arm, which self‐assembles with the same efficiency as the more rigid tris(ureidobenzyl)amines.