Environmentally Responsive Molecular Baskets: Unimolecular Mimics of Both Micelles and Reversed Micelles

ArticleinOrganic Letters 6(18):3187-9 · October 2004with5 Reads
Impact Factor: 6.36 · 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.