Environmentally responsive molecular baskets: unimolecular mimics of both micelles and reversed micelles.

Department of Chemistry, Iowa State University, Ames, Iowa 50011-3111, USA.
Organic Letters (Impact Factor: 6.14). 10/2004; 6(18):3187-9. DOI: 10.1021/ol048679p
Source: PubMed

ABSTRACT [structure: see text] When four facially amphiphilic cholate derivatives are attached to a tetraaminocalixarene scaffold, the resulting molecule responds to environmental changes by rotation of the cholate units. In polar solvents, the molecule adopts a micellelike conformation with the hydrophilic alpha-faces of the cholates pointing outward. In nonpolar solvents, it turns inside out, assuming a reversed micellelike conformation with the hydrophobic beta-faces pointing outward. Switching between the two conformations is driven by solvophobic interactions and is fully reversible.

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