The controlled self-assembly of derivatives of the concave building block g
lycoluril into three-dimensional architectures of well-defined shape and di
mension is discussed. It is-shown that the hexameric glycoluril macrocycle
cucurbituril can be applied to construct a variety of oligo- and polyrotaxa
ne assemblies. In a different approach, bis(glycoluril) compounds have been
used to form "tennis ball"- and "softball"-like assemblies which can compl
ex small guest molecules in their inner compartment and carry out reactions
between them. Finally,the self-assembling properties of molecular clip rec
eptors based on glycoluril are discussed. These clips can be modified in su
ch a way that assemblies of well-defined shape and nanosized dimension, suc
h as "golf balls", "razorblades", and "cigars", are formed in water.