Biomedical research is at the forefront of medicine, and the hydrogel materials which are formed from nanostructures are a key part of this research as it progresses through the twenty-first century. The hydrogel material provides biomedical researchers with the best tool for the simulation of in vivo extracellular conditions for the in vitro study of cells. This study focuses on the creation of dipeptide-based hydrogels by modifying the well studied diphenylalanine motif. One issue that arises in the production of dipeptide-based hydrogels is the stereochemistry of the R groups on the dipeptides that form the nanostructures. Previous research on the diphenylalanine motif has shown that the nanostructures that are formed from homochiral dipeptides resulted in a material that is unstable and over time becomes unusable. This instability occurs from the stereochemistry of the homochiral diphenylalanine as it forces the aromatic rings into a perpendicular orientation within the nanostructure, instead of the regular parallel orientation that allows for π-stacking with heterochiral diphenylalanine. To further assess this phenomenon, we used fluorinated phenylalanine to determine if it could overcome the molecular orientation issue of the amino acids by increasing the strength of intermolecular forces and inducing a rotation of the sigma bond. The induced rotation of the sigma bonds resulting in a new orientation of the molecules will allow for stable nanostructures and eliminate the need to account for stereochemistry in the production of dipeptide-based hydrogels.

Penta-fluorination of Phe-Phe motif to overcome homochirality in hierarchical self-assembly of hydrogels

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ACS Fall 2022

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