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

Abstract

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.