Chirality and self-assembly of structures derived from optically active 1,2-diaminocyclohexane and catecholamines

Abstract

Abstract Chiral biomimetic nanostructures were successfully synthesized through the oxidative polymerization of chiral and achiral catecholamines in the presence of optically active 1,2-diaminocyclohexane (DACH). Analysis of these nanostructures using circular dichroism confirmed their chiral nature, demonstrating the feasibility of inducing chirality in achiral polycatecholamine materials. Furthermore, the chiral nanostructures exhibited self-assembly behaviour, forming distinctive patterns or curly carpets-like structures on silicon surfaces. The arrangement and morphology of these structures were closely linked to the amount of DACH and its inherent chirality. Additionally, the self-assembly process was shown to be significantly influenced by the pH of the reaction and the choice of supporting materials. These findings are particularly relevant in the context of molecular self-assembly of nanoaggregates/particles generated during dopamine polymerization, suggesting a promising avenue for the development of novel chiral polycatechols-based materials.