Chirality Synchronization of Hydrogen-Bonded Complexes of Achiral N-Heterocycles.

Angew Chem Int Ed Engl

Institute of Chemistry, Organic Chemistry, Martin-Luther-University Halle-Wittenberg, Kurt-Mothes-Strasse 2, 06120, Halle/Saale, Germany.

Published: January 2017

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.

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http://dx.doi.org/10.1002/anie.201609252DOI Listing

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