Monodisperse macrospirocyclic oligomers were prepared using self-condensation of the Friedel-Crafts reaction. Through the C-9s of the central fluorene units of four surrounding oligofluorenes, four carbazole units are connected in a series to form a macrocyclic core. These rodlike oligofluorenes form a rigid three-dimensional structure, affording the resulting macrocyclics a high steric hindrance for close interchain packing.