Novel amphiphilic [2]catenanes

ORGN 77

David M. Crizer, crizerdm@jmu.edu and Kevin L. Caran, carankl@jmu.edu. Department of Chemistry, James Madison University, MSC 4501, Harrisonburg, VA 22807
When amphiphilic molecules are introduced to water or organic solvents, unique colloidal properties are often seen. These properties can then be used in applications such as drug delivery and detergents. The aim of our project is to determine if novel colloidal properties arise from the introduction of catenanes to amphiphilic molecules. Our target structures contain a polar head group, the catenane, and a nonpolar tail of various lengths. The catenane portion of the molecule contains a crown ether macrocycle threaded through a tetracationic cyclophane macrocycle. Our synthesis allows for modification of the catenane (i.e. attachment of alkyl chain) after the catenation step has been performed. This provides us access to a diversity of structures in a single step from a common catenated intermediate. The introduction of catenanes to colloidal systems has been exploited previously in the literature. Our project is unique due to the incorporation of the catenane into the amphiphilic molecule. Properties of catenanes that have been used in the field of molecular electronics, such as rocking, rattling, and rotation possibly will impart these molecules with unique properties. We also plan to study the effect of colloidal aggregation on these dynamic processes.