Probing into the Supramolecular Driving Force of an Amphiphilic β‑Cyclodextrin Dimer in Various Solvents: Host–Guest Recognition or Hydrophilic–Hydrophobic Interaction?

• Published in: The journal of physical chemistry. B Vol. 119; no. 35; pp. 11893 - 11899
• Main Authors: Bai, Yang, Fan, Xiao-dong, Yao, Hao, Yang, Zhen, Liu, Ting-ting, Zhang, Hai-tao, Zhang, Wan-bin, Tian, Wei
• Format: Journal Article
• Language: English
• Published: United States American Chemical Society 03.09.2015
• Subjects: Dimers; Ibuprofen; Micelles; Physical chemistry; Recognition; Self assembly; Solvents; Tuning
• ISSN: 1520-6106; 1520-5207
• DOI: 10.1021/acs.jpcb.5b05317

Tuning of the morphology and size of supramolecular self-assemblies is of theoretical and practical significance. To date, supramolecular driving forces in different solvents remain unclear. In this study, we first synthesized an amphiphilic β-cyclodextrin (β-CD) dimer that consists of one hydrophobic ibuprofen (Ibu) and two hydrophilic β-CD moieties (i.e., Ibu-CD2). Ibu-CD2 possesses double supramolecular driving forces, namely, the host–guest recognition and hydrophilic–hydrophobic interaction. The host–guest interaction of Ibu-CD2 induced the formation of branched supramolecular polymers (SPs) in pure water, whereas the hydrophilic–hydrophobic interaction generated spherical or irregular micelles in water/organic mixtures. The SP size increased with the increase in Ibu-CD2 concentration in pure water. By contrast, the size of micelles decreased with the increase in volume ratio of water in mixtures.