Water-Soluble Pillar[7]arene: Synthesis, pH-Controlled Complexation with Paraquat, and Application in Constructing Supramolecular Vesicles

• Published in: Organic letters Vol. 16; no. 7; pp. 2066 - 2069
• Main Authors: Li, Zhengtao, Yang, Jie, Yu, Guocan, He, Jiuming, Abliz, Zeper, Huang, Feihe
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 04.04.2014; Amer Chemical Soc
• Subjects: Anions; Chemistry; Chemistry, Organic; Hydrogen-Ion Concentration; Magnetic Resonance Spectroscopy; Microscopy, Electron, Transmission; Molecular Structure; Paraquat - chemistry; Physical Sciences; Quaternary Ammonium Compounds - chemical synthesis; Quaternary Ammonium Compounds - chemistry; Science & Technology; Solubility; Water - chemistry; RESPONSIVE COMPLEXATION; POLYMERS; NANOPARTICLES; RECOGNITION; ASSEMBLIES; CRYSTAL-STRUCTURES; DRIVEN; RELEASE; DERIVATIVES; HOST-GUEST COMPLEXATION
• ISSN: 1523-7060; 1523-7052
• DOI: 10.1021/ol500686r

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 G 1 in water was investigated. Host WP7 and guest G 1 formed a 1:1 [2]pseudorotaxane with a high association constant of (2.96 ± 0.31) × 109 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 G 2 . The morphologies and sizes of self-assemblies of G 2 and WP7⊃G 2 were identified by transmission electron microscopy and dynamic light scattering.