ORGN 228 |
| Christian R Ray, University of Illinois Urbana-Champaign, 600 S. Matthews Ave, 476 Roger Adams Lab, Urbana, IL 61801, Stefan Kraft, Kansas State University, 111 Willard Hall, Manhattan, KS 66506, Jeffery G. Saven, Department of Chemistry, University of Pennsylvania, Philadelphia, PA 19104, and Jeffrey S. Moore, Departments of Chemistry, Materials Science & Engineering, and the Beckman Institute, University of Illinois, 600 S. Mathews, Urbana, IL 61801. |
| m-Phenylene ethynylene foldamers adopt an ordered helical structure in polar solvents, generating a cavity that is able to bind hydrophobic guest molecules. Previous work has shown that modification of the cavity interior alters the binding preferences of the foldamer. To demonstrate the rational design of hosts for substrate selective binding, computational studies were performed that identified a series of m-phenylene ethynylene sequences that displayed a wide range of affinities to a rod-like guest. The inherent diversity of these sequences mandated the development of a general methodology for the rapid solid phase synthesis of phenylene ethynylene oligomers. This methodology is based on selective cleavage of silyl protecting groups and known regioselective palladium-catalyzed Sonogashira cross-coupling reactions, and will be used to synthesize the foldamer heterosequences identified in the computational study. Comparison of the predicted binding affinities with those determined experimentally will verify the ability to incorporate specific host-guest interactions into foldamer design. |
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Molecular Recognition and Self-Assembly
8:00 AM-12:00 PM, Monday, August 23, 2004 Pennsylvania Convention Center -- 201B, Oral
Division of Organic Chemistry |