Campus Units

Chemistry

Document Type

Article

Publication Version

Published Version

Publication Date

8-2006

Journal or Book Title

Journal of Organic Chemistry

Volume

71

Issue

19

First Page

7205

Last Page

7213

DOI

10.1021/jo0607663

Abstract

Amphiphilic molecular baskets were obtained by attaching facially amphiphilic cholate groups to a covalent scaffold (calix[4]arene or 1,3,5-2,4,6-hexasubstituted benzene). In a solvent mixture consisting of mostly a nonpolar solvent (i.e., CCl4) and a polar solvent (i.e., DMSO), the hydrophilic faces of cholates turned inward to form a reversed-micelle-like conformer whose stability was strongly influenced by the number of the cholates and the topology of the scaffold. Preferential solvation of the hydrophilic faces of cholates within the molecule by the polar solvent was cooperative and gave the fundamental driving force to the conformational change. The reversed-micelle-like conformer was most stable in structures that allowed multiple cholates to form a microenvironment that could efficiently enrich the polar solvent molecules from the bulk solvent mixture.

Comments

Reprinted (adapted) with permission from Journal of Organic Chemistry 71 (2006): 7205, doi:10.1021/jo0607663. Copyright 2006 American Chemical Society.

Copyright Owner

American Chemical Society

Language

en

File Format

application/pdf

Included in

Chemistry Commons

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