Self-assembly of alkylated and perfluoroalkylated scissor-shaped azobenzene dyads into distinct structures

Scissor-shaped azobenzene dyads possessing alkyl side chains can hierarchically self-assemble through a folded conformation into toroidal and tubular nanostructures. We found that the introduction of perfluoroalkyl side chains transforms the assembly pathway into direct one-dimensional stacking of the folded conformer, resulting in the formation of gel-forming supramolecular fibers that can reversibly dissociate and reassemble on exposure to light.