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The concurrent operation of two distinct hydrogen-bonding motifs, namely the carboxyl dimer supramolecular synthon (dashed lines represent hydrogen bonds) and the threading of two secondary dialkylammonium cations (black bars) through the cavity of the ditopic macrocyclic polyether bis-p-phenylene[34]crown-10 (rectangular boxes) leads to unique superstructures. The macrocyclic polyether enforces supramolecular preorganization of the carboxyl groups, permitting formation of novel doubly encircled supermolecules and interwoven supramolecular arrays in the solid state (the diagram shows a schematic representation).
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Ashton et al. (1997) studied this question.
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