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Chirality Synchronization of Hydrogen‐Bonded Complexes of Achiral N‐Heterocycles
Author(s) -
Buchs Jens,
Vogel Laura,
Janietz Dietmar,
Prehm Marko,
Tschierske Carsten
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.201609252
Subject(s) - mesophase , chirality (physics) , molecule , materials science , crystallography , phase (matter) , chemical physics , stereochemistry , chemistry , symmetry breaking , chiral symmetry breaking , organic chemistry , physics , quantum mechanics , nambu–jona lasinio model
2,4‐Diamino‐6‐phenyl‐1,3,5‐triazines carrying a single oligo(ethylene oxide) (EO) chain form an optically isotropic mesophase composed of a conglomerate of macroscopic chiral domains with opposite sense of chirality even though the constituent molecules are achiral. This mesophase was proposed to result from the helical packing of hydrogen‐bonded triazine aggregates, providing long‐range chirality synchronization. The results provide first evidence for macroscopic achiral symmetry breaking upon conglomerate formation in an amorphous isotropic phase formed by hydrogen‐bonded associates of simple N‐heterocycles that are related to prebiotic molecules.