Effect of aromatic core on the supramolecular chirality of l-phenylalanine derived assemblies

Abstract

Constructing chiral supramolecular assemblies with controllable handedness has attracted much attention in materials science, biology and chemistry, owing to their outstanding photophysical properties and novel biological effects. Herein, four gelators derived from l-phenylalanine were synthesized and their gel formation and self-assembled nanostructures were investigated. It was found that the handedness, helical pitch and diameter of these self-assemblies were successfully controlled by tuning the structure of central aromatic groups. Left- and right-handed nanofibers with different dimensions were obtained, showing configuration-regulated assembly behavior. These self-assemblies were further characterized by CD, FTIR, SEM, and UV–vis, and the results suggested that the π-π stacking among the central aromatic rings and hydrogen bonds among the amide groups at the terminals play important roles in the formation of these self-assemblies.