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Synergy of Axial and Point Chirality to Construct Helical N ‐Heterotriangulene‐Based Supramolecular Polymers
Author(s) -
Dorca Yeray,
Valera Jorge S.,
Cerdá Jesús,
Aragó Juan,
Gómez Rafael,
Ortí Enrique,
Sánchez Luis
Publication year - 2018
Publication title -
chemnanomat
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.947
H-Index - 32
ISSN - 2199-692X
DOI - 10.1002/cnma.201800186
Subject(s) - supramolecular chemistry , stereocenter , chirality (physics) , supramolecular polymers , stacking , amide , axial chirality , polymer , crystallography , materials science , stereochemistry , chemistry , polymer chemistry , enantioselective synthesis , crystal structure , physics , organic chemistry , chiral symmetry breaking , catalysis , composite material , symmetry breaking , nambu–jona lasinio model , quantum mechanics
We report on the cooperative supramolecular polymerization of a series of N ‐heterotriangulenes that aggregate into helical columnar stacks by the operation of H‐bonding interactions between the peripheral amide groups and π‐stacking of the central aromatic moieties. The helical outcome of the highly stable supramolecular polymers stems from the joint effect of the point chirality dictated by the stereogenic centers at the side chains that, in turn, conditions the molecular atropisomerism generated by the restricted rotation of the peripheral benzamide moieties affording a propeller‐like geometry. To the best of our knowledge, this is the first example in which two different elements of asymmetry act together to bias the helicity of chiral supramolecular polymers.