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 Contributor Abstract 

Stephen F. Nelsen

   65th Birthday Symposium
Madison, Wisconsin
June 3-4, 2005

Luis Echegoyen

Clemson University, 219 Hunter Laboratories, Clemson, SC 29634

Pyrrolidine Adducts of Fullerenes: Regioselective Synthesis of Multiple Adducts and of Endohedral Compounds

Because of its unique redox properties, C₆₀ has found useful applications in films and monolayers, mainly in the construction of photovoltaic devices. One of the problems that still remains in this area is how to “connect” the fullerenes in such a way that their unique redox properties can be exploited in molecular electronic devices. Single C₆₀ molecular transistors have been reported, the principle based on electromechanical oscillatory properties of the molecule, not on the redox properties. We recently described a pyridyl-pyrrolidine adduct on C₆₀, see structure 1, and it seems to provide effective electronic coupling between the pyridyl nitrogen and the fullerene core. Based on this principle, we have designed and synthesized a trans-1-bis-pyridyl-pyrrolidine compound, 2, for effective linear connectivity of the fullerene core to external metal surfaces. Other bis- and tris-adducts have also been designed and synthesized in regioisomerically pure form using similar concepts. These synthetic schemes will be presented and discussed, along with other pyrrolidine derivatives of Sc₃N@C₈₀ and their properties.

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