Water-soluble pillar[7]arene: synthesis, pH-controlled complexation with paraquat, and application in constructing supramolecular vesicles

Abstract

By the introduction of 14 anionic carboxylate groups at its two rims, a water-soluble pillar[7]arene (WP7) was synthesized. Its pH-controlled complexation with paraquat G1 in water was investigated. Host WP7 and guest G1 formed a 1:1 [2]pseudorotaxane with a high association constant of (2.96 ± 0.31) × 10(9) M(-1) in water. Furthermore, we took advantage of this novel molecular recognition motif to fabricate a supra-amphiphile based on WP7 and an amphiphilic paraquat derivative G2. The morphologies and sizes of self-assemblies of G2 and WP7⊃G2 were identified by transmission electron microscopy and dynamic light scattering.