Many abiotic foldamers are composed of achiral parts but adopt chiral geometries, like helices. In these systems, there is no inherent preference for one handedness of the fold. Ortho-phenylenes are a class of aromatic foldamers that fold into helices driven by arene-arene stacking interactions. Although their folding is now reasonably understood, it is not clear what direction the ortho-phenylene helix will twist when a chiral guest is bound. Here, we use CD spectroscopy to report that the addition of a chiral ammonium ion molecule to a crown-ether appended ortho-phenylene can induce a preferred handedness. We attempt to demonstrate control over this mechanism by choosing chiral groups to favor one orientation.
Author: Molly Bookout
Advisors: Dr: Scott C. Hartley. Department of Chemistry and Biochemistry,
Sumalatha Peddi, Department of Chemistry and Biochemistry
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