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Hierarchy of Asymmetry at Work: Chain‐Dependent Helix‐to‐Helix Interactions in Supramolecular Polymers
Author(s) -
DíazCabrera Sandra,
Dorca Yeray,
Calbo Joaquín,
Aragó Juan,
Gómez Rafael,
Ortí Enrique,
Sánchez Luis
Publication year - 2018
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.201706070
Subject(s) - helix (gastropod) , hierarchy , asymmetry , supramolecular chemistry , macromolecule , chirality (physics) , side chain , polymer , chemistry , chain (unit) , stereochemistry , crystallography , chemical physics , physics , crystal structure , biology , organic chemistry , biochemistry , ecology , nambu–jona lasinio model , chiral symmetry breaking , quantum mechanics , astronomy , snail , economics , market economy , quark
A detailed investigation of the hierarchy of asymmetry operating in the self‐assembly of achiral ( 1 ) and chiral ( ( S )‐2 and ( R )‐3 ) 1,3,5‐triphenylbenzenetricarboxamides (TPBAs) is reported. The aggregation of these TPBAs is conditioned by the point chirality at the peripheral side chains for ( S )‐2 and ( R )‐3 . An efficient helix‐to‐helix interaction that goes further in the organization of fibrillar bundles is experimentally detected and theoretically supported only for the achiral TPBA 1 . The effective interdigitation of the achiral aliphatic side chains produces a social self‐sorting to form preferentially heterochiral macromolecular aggregates.
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