Self-assembling supramolecular objects with π-electron functionality are of increasing interest for nanotechnology. The vast majority of these approaches involve the association of molecular components in organic solvents. Notable exceptions are the water-soluble rod-coil oligophenylenes, but they are rendered soluble by oligo(ethylene oxide)s known in many cases to resist specific biological adhesion. Thus, the construction of discrete organic electronic nanostructures with biologically interactive function in aqueous environments remains a daunting challenge. We demonstrate herein how small peptide sequences with π-conjugated oligomers directly embedded in the backbone promote assembly into 1-D nanostructures with strong n-n intermolecular electronic communication under completely aqueous and physiologically relevant conditions. This important step sets the stage for the presentation of bioactive small peptides and other molecular recognition elements on the periphery of the nanostructure. The synthetic approach is fundamentally different from covalent modification of preformed nanostructures or single proteins in that the peptidic structure encourages or enforces the formation of π-stacked conduits within the assembled objects.
展开▼
