Self-association and self-assembly of molecular clips in solution and in the solid state

Clip molecules based on diphenylglycoluril form well-defined dimeric structures in chloroform solution and in the solid state. In solution the dimerization process is based on favourable pi-pi interactions and cavity filling effects. A combination of favourable pi-pi interactions and crystal packing forces determine the self-assembly of clips in the solid state. The geometry that the clip molecules adopt in solution and in a series of X-ray crystal structures is compared with favourable geometries predicted by molecular modelling calculations. (C) 2002 Elsevier Science Ltd. All rights reserved.