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Chirality synchronization of hydrogen-bonded complexes of achiral N-heterocycles

: Buchs, Jens; Vogel, Laura; Janietz, Dietmar; Prehm, Marko; Tschierske, Carsten


Angewandte Chemie. International edition 56 (2017), No.1, pp.280-284
ISSN: 1433-7851
ISSN: 0044-8249
ISSN: 0570-0833
ISSN: 1521-3773
Bundesministerium für Bildung und Forschung BMBF
Spitzenforschung und Innovation in den neuen Ländern; 03IS2201C
Taschentuchlabor - Impulszentrum für Integrierte Bioanalyse
Journal Article
Fraunhofer IAP ()

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.