Of particular interest are ortho-Phenylenes due to their ability to form helices, thus classifying them as foldamers. Molecules that are of this classification are of particular interest due to their potential to mimic biomolecules, thus making them available to use for practical applications. The understanding of ortho-phenylene folding is crucial in order to assemble higher order structures. In past studies, we were able to confirm that twist sense control of ortho-phenylenes could be controlled with the introduction of imine functional groups at the terminal end of the helix; however, in order to improve on this finding, we attempted to develop a method of controlling twist sense of an ortho-phenylene heptamer with the introduction of a chiral phthalimide substituent at the middle of the chain. We believed that this would leave the terminal ends of the chain open for further possible reactions, with the ultimate goal being to create large macrocycles with complex structures. However, due to obstacles in the synthesis, we were only able to synthesize a trimer product which is a result of one-sided coupling. In an attempt to resolve this issue, we plan to use a new starting material with a bromo leaving group in order to minimize this effect, thus making the synthesis of the desired pentamer product, and eventually the substituted heptamer product, feasible.
Author: Juliana Livieri
Faculty Advisor: C. Scott Hartley, Department of Chemistry and Biochemistry
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