Investigating the Folding and Fibril-forming Behaviors of AAN- and NDI-Containing Foldamers

Aromatic foldamers containing 1,4,5,8-naphthalenetetracarboxylic diimide (NDI) and 1,5-dialkoxynaphthalene (DAN) in alternation have been shown to assemble into supramolecular structures and, when heated, irreversibly aggregated fibrils. By replacing electron-rich DAN with similarly electron-rich aminoalkoxynaphthalene (AAN) in a similarly alternating peptide, we hypothesize that we can form similar stacked and fibril structures when the two monomers are connected by patterned charged and hydrophobic amino acids. Notably, AAN has a pKa of approximately 5, meaning pH can be used as a switch to alter the charge state of AAN, which we hypothesize can be used to alter the stacked or aggregated structure of the peptide as a whole. Presently, syntheses toward peptides with high fibril-forming propensities are being optimized, with the aim of studying their behaviors in response to pH modulation. In this work, we have also explored the π stacking and charge transfer behavior of an AAN- and NDI-containing peptide in both neutral and acidic environments.Bachelor of Scienc