Dynamic chiral selection and amplification using photoresponsive organogelators.
The ability to select, amplify, and lock dynamic equilibria is of great interest into understanding and applying chiral systems in Nature. The dynamic equilibrium between P and M helicity of a nonchiral diarylethene switch 3 could selectively be coaggregated in the gel state by complementary chiral switches 1 and 2 (that itself is also subjected to the same equilibrium between P and M helicity). Enantiomeric excess as high as 94% was observed during this dual task for 1 and 2 (arranging itself and 3 in only one conformation during aggregation). Interestingly, opposite chiral induction was observed, although the conformation of both 1 and 2 is R.
de Jong
Jaap J D
JJ
Laboratory of Organic Chemistry, Stratingh Institute, University of Groningen, Nijenborgh 4, 9747 AG Groningen, The Netherlands.
Tiemersma-Wegman
Theodora D
TD
van Esch
Jan H
JH
Feringa
Ben L
BL
D005030:Ethylenes / Q000138:chemical synthesis* / Q000737:chemistry / Q000528:radiation effects*; D005782:Gels / Q000138:chemical synthesis / Q000737:chemistry / Q000528:radiation effects; D006860:Hydrogen Bonding; D015394:Molecular Structure; D008970:Molecular Weight; D010777:Photochemistry
D005030:Ethylenes; D005782:Gels