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.

Comments

Reprinted (adapted) with permission from Journal of Organic Chemistry 70 (2005): 7585, doi:10.1021/jo051127f. Copyright 2005 American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

Included in

Chemistry Commons

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