Diyne-Functionalized Fullerene Self-Assembly for Thin Film Solid-State Polymerization

C60 fullerene derivatives bearing aliphatic chains can self-assemble into versatile supramolecular structures. Cross-linking of such self-assembled morphologies is an attractive approach to enhance the structural stability of these self-organized structures. We describe the synthesis of a C60 functionalized with a single alkyl chain bearing a diacetylene moiety. In a thin film, the molecule self-assembles into lamellar arrays. The character of the side chain attached to the fullerene is key to the observed packing ability. The stabilization proceeds through solid-state polymerization of the diacetylene moieties. By blending the fullerene derivative with a cyanine dye, various nanostructured fullerene morphologies are obtained that can be selectively stabilized by thermal polymerization. These films can serve as basis for nanostructured fullerene scaffolds that can find applications in optics and electronics.