Barrel-Like Molecular Architecture from Folded Oligomers

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The focus of this research is the preparation of novel molecular architectures as candidates for catalytic scaffolding. The basic design of the targeted oligo(phenylene ethynylene)s involves attaching polar side groups to the oligomer's non-polar hydrocarbon backbone. Secondary helical structure is then realized from a conformation in which the oligomer folds back upon itself such that the aromatic rings stack face-to-face along the helix axis. This approach to the development of new catalysts benefits from the enormous molecular diversity available through sequence modification, the full three-dimensional definition of these spontaneously organized tubular compartments and the intrinsic chirality of the helix. The proposed catalysts hold the promise of being more robust that proteins and have the potential to catalyze a wide range of organic reactions. The deracemization of alpha-chiral acids is an example. With this renewal award, the Organic and Macromolecular Chemistry Program is supporting the research of Dr. Jeffrey S. Moore of the Department of Chemistry at the University of Illinois. Professor Moore will focus his work on the molecular design, synthesis and study of oligo(phenylene ethynylene)s that fold into helical conformations, thereby creating tubular cavities. These solvophobically driven helical structures produce a shape that is reminiscent of the most common active site domain observed in enzymes, the alpha/beta-barrel motif. Thus, a long term goal of the research is to use this barrel-like scaffolding as an architecture for catalyst discovery.