4.8 Article

Autoamplification of Molecular Chirality through the Induction of Supramolecular Chirality

Journal

ANGEWANDTE CHEMIE-INTERNATIONAL EDITION
Volume 53, Issue 20, Pages 5073-5077

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.201311160

Keywords

chirality; gels; hydrogen bonds; self-assembly; supramolecular chemistry

Funding

  1. European Research Council [227897]
  2. Ministry of Education, Culture and Science of the Netherlands [024.001.035]
  3. US National Science Foundation (NSF International Postdoctoral Fellowship) [OISE-0853019]

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The novel concept for the autoamplification of molecular chirality, wherein the amplification proceeds through the induction of supramolecular chirality, is presented. A solution of prochiral, ring-open diarylethenes is doped with a small amount of their chiral, ring-closed counterpart. The molecules co-assemble into helical fibers through hydrogen bonding and the handedness of the fibers is biased by the chiral, ring-closed diarylethene. Photochemical ring closure of the open diarylethene yields the ring-closed product, which is enriched in the template enantiomer.

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