Title
Solvent-Tunable Binding of Hydrophilic and Hydrophobic Guests by Amphiphilic Molecular Baskets
Campus Units
Chemistry
Document Type
Article
Publication Version
Published Version
Publication Date
8-2005
Journal or Book Title
Journal of Organic Chemistry
Volume
70
Issue
19
First Page
7585
Last Page
7591
DOI
10.1021/jo051127f
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.
Copyright Owner
American Chemical Society
Copyright Date
2005
Language
en
File Format
application/pdf
Recommended Citation
Zhao, Yan and Ryu, Eui-Hyun, "Solvent-Tunable Binding of Hydrophilic and Hydrophobic Guests by Amphiphilic Molecular Baskets" (2005). Chemistry Publications. 197.
https://lib.dr.iastate.edu/chem_pubs/197
Comments
Reprinted (adapted) with permission from Journal of Organic Chemistry 70 (2005): 7585, doi:10.1021/jo051127f. Copyright 2005 American Chemical Society.