NMR characterisation of substituted fullerenes

• NMR characterisation of substituted fullerenes

- with Prof. Steve Pyne and A/Prof. Paul Keller, University of Wollongong.
Since its discovery in 1985, [60]-fullerene (C₆₀) and its homologues have shown promise for exciting new developments and applications in areas such as medicinal chemistry and materials science. The synthetic goals of this work, carried out at the University of Wollongong, involves developing methods for preparing optically active, multi-functionalized fullerene derivatives in a regioselective and diastereoselective manner and investigating their applications. At UNSW, we are using NMR spectroscopy as a robust and definitive technique for the assignment of regiochemistry in these compounds.

A trans-4 difunctionalized fullerene and an INADEQUATE NMR experiment used to identify the substitution pattern.

References:
Ball, G.E.; Burley, G.A.; Chaker, L.; Hawkins, B.C.; Williams, J.R.; Keller, P.A.; Pyne, S.G. "Structural reassignment of the mono- and bis-addition products from the addition reactions of N-(Diphenylmethylene)glycinate esters to [60]fullerene under Bingel conditions." J. Org. Chem., 2005, 70, 8572.