Porous materials from self-assembling cyclic ureas

ORGN 208

Linda S. Shimizu, shimizul@mail.chem.sc.edu, Department of Chemistry and Biochemistry, University of South Carolina, 631 Sumter St., Columbia, SC 29208
There is great interest in the development of new building blocks that predictably self-assemble into well-defined supramolecular structures. We have previously shown that small rigid bis-urea macrocycles assemble into tubular structures through the well-established urea-urea hydrogen bonding motifs. These ‘tubes' further pack together into microcrystalline materials. We are trying to understand the rules that govern the assembly of these monomers into single columns and further into bundles, aggregates, and crystals. The microcrystalline assemblies of a large phenylether derivative have remarkable host-guest properties and reversibly bind and exchange guest molecules (Figure 1). We report here a systematic study of the binding properties of a large phenylether derivative as well as the synthesis and assembly of more soluble urea derivatives. We will also describe our progress towards a non-covalent capping agent that could be used stoichiometrically to regulate assembly size and solubility.

 

Molecular Recognition and Self-Assembly
8:00 AM-12:00 PM, Monday, 27 March 2006 Georgia World Congress Center -- C302, Oral

Division of Organic Chemistry

The 231st ACS National Meeting, Atlanta, GA, March 26-30, 2006