Peptoids are a class of peptidomimetic polymers composed of N-substituted glycine repeating units. We have previously demonstrated that the monomer sequence of peptoids can be specifically tailored to yield amphiphilic material that self-assembles in aqueous conditions into two-dimensional, hundreds of microns wide, robust nanosheets. These nanosheets assemble via a critical reversible monolayer intermediate, which undergoes irreversible collapse upon compression to form nanosheet bilayers. Herein, we incorporate N-phenylglycine residues as the hydrophobic monomers to enforce the trans-amide backbone configuration at every other residue. We envision that such a conformational bias will favor adsorption at the air-water interface, while simultaneously disfavoring peptoid collapse in water. The synthesis of N-phenylglycine-rich amphiphilic peptoids up to 16 residues in length will be presented. New efficient submonomer coupling methods were developed that exploit the novel addition of heavy metal salts in order to incorporate weak nuclophiles like aniline. Using this method, we generated a series of amphiphilic peptoids with electron rich and electron poor aromatic rings to modulate and probe the role of packing interactions in the hydrophobic core of the nanosheet. The monolayer compression behavior of these peptoids will be described, along with preliminary assembly data.

Influence of backbone flexibility on the 2D assembly of peptoid nanosheets

248th National Meeting (2014)

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