Zhao Yan, Ryu Eui-Hyun
Department of Chemistry, Iowa State University, Ames, Iowa 50011-3111, USA.
J Org Chem. 2005 Sep 16;70(19):7585-91. doi: 10.1021/jo051127f.
[reaction: see text] Responsive amphiphilic molecular baskets were obtained by attaching four facially amphiphilic cholate groups to a tetraaminocalixarene scaffold. Their binding properties can be switched by solvent changes. In nonpolar solvents, the molecules utilize the hydrophilic faces of the cholates to bind hydrophilic molecules such as glucose derivatives. In polar solvents, the molecules employ the hydrophobic faces of the cholates to bind hydrophobic guests. A water-soluble basket can bind polycyclic aromatic hydrocarbons including anthracene, pyrene, and perylene. The binding free energy (-deltaG) ranges from 5 to 8 kcal/mol and is directly proportional to the surface area of the aromatic hosts. Binding of both hydrophilic and hydrophobic guests is driven by solvophobic interactions.
