Dynamic chiral selection and amplification using photoresponsive organogelators

J Am Chem Soc. 2005 Oct 12;127(40):13804-5. doi: 10.1021/ja055268a.

Abstract

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.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ethylenes / chemical synthesis*
  • Ethylenes / chemistry
  • Ethylenes / radiation effects*
  • Gels / chemical synthesis
  • Gels / chemistry
  • Gels / radiation effects
  • Hydrogen Bonding
  • Molecular Structure
  • Molecular Weight
  • Photochemistry

Substances

  • Ethylenes
  • Gels