Molecular assemblies provide a means of evaluating intermolecular forc
es and chemical information involved in recognition processes. Self-co
mplementary molecules are especially useful in this regard, and here a
re described synthetic structures inspired by sports equipment. These
molecules dimerize through hydrogen bonding to generate pseudo-spheric
al capsules. Their assembled states are capable of reversible encapsul
ation of smaller molecules of complementary size and shape. The unusua
l thermodynamic parameters observed for the encapsulation process sugg
est a host-hostage relationship. The capsules show promise as reaction
chambers.