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Herein, we report the synthesis of a novel porous polymer, PS2, containing radially π-conjugated carbocycles and a linear phenylene backbone. The PS2-based membrane has a distinct small size cutoff (ca. 2.6 nm) and a major size at ∼1.5 nm for the size-selective separation of nanoparticles.

Direct π-extension by the Scholl reaction for solution-based growth of armchair edges in curved macrocyclic hydrocarbon nanostructures is a great challenge. To date, several attempts at direct π-extension of small highly strained macrocycles have failed. Herein, we report a fixed two-bond approach for direct functionalization of small strained macrocyclic nanorings. The reaction occurs selectively to produce large π-extended molecular crowns with high yields. The design of these precursors features two peripheral C-C bonds that are readily incorporated into the extended aromatic moiety to overcome strain-induced side reactions, such as 1,2-phenyl shift. The crown-shaped macrocycle