Functional self-assembly of hydrogen-bonded networks. Construction of aromatic stacks and columns and cavity-size control via flexible intercalation of 1D chains having orthogonal aromatic substituents

Anthracene-monoresorcinol derivative 1 forms hydrogen-bonded poly(resorcinol) 1D chains, which self-assemble via interpenetration or intercalation of the orthogonal anthracene (A) substituents. Guest-binding in the resulting cavities leads to either, depending on the guests (G, aromatic or aliphatic), an alternate ... A . G . A . G ... (monomeric) or an ... A . A . G . G ...(dimeric) lattice pattern. The monomeric lattices show a remarkable linear-alkyl vs branched-alkyl selectivity in the guest-binding. The dimeric lattices are characterized by their exclusive emission of excimer fluorescence. Self-assembly of the present 1D chains is thus functional and also flexible and dynamic; removal, addition, and exchange of guest molecules readily occur in the solid states.