[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.
[Show abstract][Hide abstract] ABSTRACT: The use of natural compounds in the preparation of new materials can improve the biocompatibility of the materials and avoid
any potential toxicity of the degradation products when used for biomedical applications. Bile acids are amphiphilic molecules
biosynthesized in the liver. They are used to prepare various polymers and oligomers. These polymers made of bile acids are
promising materials in both biomedical and pharmaceutical fields.
Science in China Series B Chemistry 07/2009; 52(7):849-861. DOI:10.1007/s11426-009-0124-x · 1.20 Impact Factor
[Show abstract][Hide abstract] ABSTRACT: [reaction: see text] Several water-soluble calixarenes were synthesized via Huisgen 1,3-dipolar cycloaddition between azides and alkynes. Cationic, anionic, and nonionic calixarenes were prepared from a common azidocalixarene intermediate. Azidocalixarenes performed better than alkynylcalixarenes as precursors. The aggregation behavior of the water-soluble calixarenes was studied by (1)H NMR spectroscopy.
[Show abstract][Hide abstract] ABSTRACT: A cholate derivative with three epoxide groups was synthesized from cholic acid by allylation followed by epoxidation. Ring opening of the epoxides by various nucleophiles yielded facial amphiphiles with anionic, cationic, or nonionic functional groups. The critical micelle concentrations of these amphiphiles largely depend on the number of charged groups on the molecule. A facial amphiphile with pH-tunable micellization was prepared. Its aggregation behavior changes abruptly at pH = 7.6-6.6 as a result of protonation of its amino groups.
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