Molecules with self-complementary surfaces interact through weak inter
molecular forces to form assemblies, and the assembled states frequent
ly exhibit distinctive properties. Described here are systems in which
symmetrical molecules assemble through hydrogen bonding to produce ca
psules 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 g
uests, Molecular recognition of chiral guests, such as naturally occur
ring terpenes, determines which dissymmetric cavities are preferential
ly formed in the assembly process.