Date of Award

1995

Document Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry

First Advisor

Peter W. Rabideau

Abstract

This dissertation deals with the synthesis and characterization of polynuclear aromatic hydrocarbons with curved surfaces whose carbon frameworks may be identified on the C$\sb{60}$ surface. C$\sb{60},$ known as buckminsterfullerene, is the most important member of the fullerene family, the recently discovered new form of elemental carbon. Chapter one presents the synthesis and the dynamic $\sp1$H NMR behavior of cyclopentacorannulene (CPC), the first conformationally "locked", fullerene-related, bowl-shaped aromatic hydrocarbon. The determined barrier for the ring inversion of the dihydro CPC is more than twice as large as that of corannulene. In contrast to the crystal structure of corannulene, the crystal structure of the unsaturated cyclopentenocorannulene shows remarkable long range bowl stacking in a concave-convex orientation. Chapter two presents the synthesis and characterization of the first two known semibuckminsterfullerenes (C$\rm\sb{30}H\sb{12}).$ These polynuclear aromatic hydrocarbons represent one half of C$\sb{60}.$.

Pages

144

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