A Saddle-Shaped Expanded Porphyrinoid Fitting C60

We present the synthesis of a new type of an expanded porphyrinoid macrocycle with a saddle-shaped morphology and its complexation of C60 guest molecules. The new macrocycle contains four carbazole and four triazole moieties and can be readily synthesized via a copper-catalyzed click reaction. It shows specific photo-physical properties including fluorescence with a high quantum yield of 60 %. The combination of the saddle-shaped geometry with the expanded π-system allows for host–guest interactions with C60 in a stacked polymer fashion. Evidence for the presence of a host–guest complex is provided both in solution by NMR spectroscopy and in the solid state by X-ray structure analysis.