Chemistry Publications Chemistry 8-2005 Solvent-Tunable Binding of Hydrophilic and Hydrophobic Guests by Amphiphilic Molecular Baskets Yan Zhao Iowa State University,
[email protected] Eui-Hyun Ryu Iowa State University Follow this and additional works at: http://lib.dr.iastate.edu/chem_pubs Part of the Chemistry Commons The ompc lete bibliographic information for this item can be found at http://lib.dr.iastate.edu/ chem_pubs/197. For information on how to cite this item, please visit http://lib.dr.iastate.edu/ howtocite.html. This Article is brought to you for free and open access by the Chemistry at Iowa State University Digital Repository. It has been accepted for inclusion in Chemistry Publications by an authorized administrator of Iowa State University Digital Repository. For more information, please contact
[email protected]. Solvent-Tunable Binding of Hydrophilic and Hydrophobic Guests by Amphiphilic Molecular Baskets Abstract 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 (−ΔG) 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. Disciplines Chemistry Comments Reprinted (adapted) with permission from Journal of Organic Chemistry 70 (2005): 7585, doi:10.1021/ jo051127f.