Self-Assembling Molecular Capsules

Host complexes formed through non-covalent interactions comprise a rapidly growing area of supramolecular chemistry. In particular, three-dimensional hosts which reversibly encapsulate guests hold great potential as both novel tools in chemistry and as biological models. Here, we describe the design, synthesis, and study of several selfassembling molecular capsules. In particular, we discuss how challenges encountered with earlier capsules were overcome using a modular strategy based upon unique glycoluril building blocks. This method generated capsules approaching nanoscale dimensions that were studied using a combination of NMR and ESI-mass spectrometry. Progress toward novel supramolecular capsules which utilize both hydrogen bonds and metal-ligand interactions is reported and new ferric iron sequestering agents are introduced. Thesis Supervisor: Title: Professor Julius Rebek, Jr. Director, The Skaggs Institute for Chemical Biology and Professor, Department of Chemistry The Scripps Research Institute