ORGN 837 |
| The convex surface of fullerenes is particularly well-suited for its molecular recognition by concave conjugated fragments. Several bowl and belt-shaped fullerene receptors based on this concave-convex complementarity principle have already been reported. Herein, we report two novel electroactive TTF-type receptors as supramolecular partners for fullerenes. Firstly, we describe the first exTTF-based receptor for fullerene, based on a synthetically straightforward tweezer-like design. Despite its structural simplicity, our receptor associates fullerene efficiently in both chlorobenzene and CHCl3/CS2 mixtures (Kassoc > 103 M-1). Moreover, it shows a unique solvent-controlled positive homotropic cooperative binding behavior. Secondly, we report the synthesis, X-ray, spectroscopic, electrochemical and theoretical characterization of a new family of Ĉ-extended TTF derivatives as bowl-shaped electroacive monotopic receptors for fullerenes. The possibility of exploiting the elegant simplicity of these novel supramolecular systems and the electronic and electrochemical properties of their components in the bottom-up construction of nanosized devices is currently under investigation.
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Molecular Recognition and Self-Assembly
1:00 PM-5:00 PM, Thursday, March 29, 2007 McCormick Place Lakeside -- Room E351, Level 3, Oral
Division of Organic Chemistry |
