Synthesis of a rigid "ball-and-chain" donor-acceptor system through Diels-Alder functionalization of buckminsterfullerene (C60)

Encouraged by our recent results in the functionalization of C[sub 60] through Diels-Alder reactions, we sought to develop a novel type of derivative of C[sub 60] by creating ball-and-chain systems, in which the C[sub 60] unit and another functional group, G, are attached to a rigid polycyclic chain or bridge. These systems should provide unprecedented insight into a variety of long-range intramolecular processes between C[sub 60] and G, including energy and electron transfer, and would complement the corresponding intermolecular processes studied so far. We are pleased to report the synthesis of our first ball-and-chain molecule in which the chain comprises a rigid polynorbornyl-bicyclo[2.2.0]hexyl bridge which has been used extensively by the UNSW group in the construction of several donor-bridge-acceptor systems. The key feature of the present work is the Diels-Alder reaction between C[sub 60] and a novel bridge diene affording the ball-and-chain adduct. 18 refs., 1 fig.