Journal
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 56, Issue 1, Pages 280-284Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201609252
Keywords
chirality; conglomerates; heterocycles; hydrogen bonds; self-assembly
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Funding
- BMBF Initiative Spitzenforschung und Innovation in den neuen Landern within the cooperative project Taschentuchlabor-Impulszentrum fur Integrierte Bioanalyse [FKZ 03IS2201C]
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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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