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A macrobicyclic ether-ketone oligomer containing twenty aromatic rings has been isolated from the products of nucleophilic condensation between 4,4′-(9-fluorenylidene)diphenol and 1,3,5-tris(4′-fluorobenzoyl)benzene. Reduction of all six carbonyl groups to methylene units yields a derivative which exhibits non-covalent dimerisation in the crystalline state via shape-complementary interlocking of fluorenylidene-containing “loop” regions.

Non-covalent dimerisation of a bicyclic aromatic oligomer via loop–loop interlocking in the solid state