Chiral spaces: dissymmetric capsules through self-assembly

Science. 1998 Feb 13;279(5353):1021-3. doi: 10.1126/science.279.5353.1021.


Molecules with self-complementary surfaces interact through weak intermolecular forces to form assemblies, and the assembled states frequently exhibit distinctive properties. Described here are systems in which symmetrical molecules assemble through hydrogen bonding to produce capsules with dissymmetric cavities. The capsules form and dissipate on a time scale that permits their direct observation by nuclear magnetic resonance measurements, and they act as hosts for smaller molecular guests. Molecular recognition of chiral guests, such as naturally occurring terpenes, determines which dissymmetric cavities are preferentially formed in the assembly process.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, P.H.S.

MeSH terms

  • Bridged Bicyclo Compounds, Heterocyclic / chemistry*
  • Chemical Phenomena
  • Chemistry, Physical
  • Dimerization
  • Hydrogen Bonding
  • Magnetic Resonance Spectroscopy
  • Models, Chemical
  • Models, Molecular
  • Stereoisomerism*
  • Succinimides / chemistry*
  • Thermodynamics


  • Bridged Bicyclo Compounds, Heterocyclic
  • Succinimides