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Pure Appl. Chem., 2008, Vol. 80, No. 3, pp. 571-587

Amphiphilic architectures based on fullerene and calixarene platforms: From buckysomes to shape-persistent micelles

Andreas Hirsch

Department of Chemistry and Pharmacy and Interdisciplinary Center of Molecular Materials (ICMM), Friedrich-Alexander University Erlangen-Nürnberg, Henkestrasse 42, D-91054 Erlangen, Germany

Abstract: The supramolecular aggregation properties of new prototypes of artificial amphiphiles consisting of fullerene or calixarene building blocks serving as platforms for the connection of hydrophobic and dendritic hydrophilic groups are reported. Very water-soluble monoadducts of C60 carrying a defined number of negative charges at a given pH were hybridized with cationic porphyrins including cyctochrome C and investigated with respect to photoinduced electron transfer. Fullerene adducts with dendritic deprotected sugar addends self-assemble to supramolecular sugar balls in water with a narrow size distribution of the micelles of around 4 nm. Various examples of cone- or T-shaped amphiphiles involving calixarene and fullerene cores self-organize to the first examples of shape-persistent micelles whose supramolecular arrangement in water has been determined with unprecedented precision based on the analysis of cryo-transmission electron microscopy (TEM) investigations.