Great progress has been made toward the design of secondary structure in abiotic foldamers. However, to mimic the function and behavior of proteins, well defined tertiary structure must be achieved. The self-assembly of foldamers into macrocyclic cages is a simple approach to tertiary structure. The molecular backbone chosen for our foldamer cages is the ortho-phenylenes. The ortho-phenylenes are desirable given that their folding in solution can be characterized in detail using NMR spectroscopy. The assembly of ortho-phenylene hexamers or decamers with one of three vertices to give [2+3] cages through imine condensation has been studied. Each vertex has a different bite angle, which forces folding into different conformations. Due to the complex geometric structure of the desired cage, the question of interaction between folding and self-assembly is to be investigated. Optimization of the formation conditions and characterization of the [2+3] foldamer cage will be discussed.
Author(s): Marissa Fornadel, Chemistry and Environmental Science Major
Advisor(s): Scott Hartley, Department of Chemistry and Biochemistry
Roshan Lama, Department of Chemistry and Biochemistry
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