Aqueous Assembly of Zwitterionic Daisy Chains

Abstract

Abstract The synthesis and characterization of zwitterionic molecular [ c 2]‐ and [ a 2]‐daisy chains are described, relying on recognition of a positively charged cyclophane and a negatively charged oligo(phenylene‐ethynylene) (OPE) rod in aqueous medium. For this purpose, syntheses of an acetylene‐functionalized macrocyclic receptor and a water‐soluble OPE‐rod as the guest component are presented, from which a heteroditopic daisy chain monomer was prepared. This monomer aggregated strongly in water/methanol 4:1 and formed molecular daisy chains, which were isolated as interlocked species from a stoppering reaction at 1 m m concentration. The cyclic dimer [ c 2] was the main product with an isolated yield of 30 % and consisted of a mixture of diastereomers, as evidenced by 1 H NMR spectroscopy.