1613317-63-7Relevant articles and documents
Autoamplification of molecular chirality through the induction of supramolecular chirality
Vandijken, Derk Jan,Beierle, John M.,Stuart, Marc C. A.,Szymanski, Wiktor,Browne, Wesley R.,Feringa, Ben L.
, p. 5073 - 5077 (2014/05/20)
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. There and back again: Doping a mixture of rapidly interconverting prochiral, open diarylethenes (left) with their enantiopure, closed counterparts, led to formation of gel fibers of preferred helicity (center). This supramolecular chirality was transferred to the molecular level by photochemical ring closing, thus yielding a chiral product (right) which is enriched in the enantiomer originally used as a template.
