Date of Award

1998

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 novel intermediate target molecules that when placed under pyrolytic conditions, yield polynuclear aromatic hydrocarbons that can be identified on the surface of buckminsterfullerene. It also presents some direct applications that have developed from some significant synthetic improvements of key intermediates required for production of novel fullerene fragments. Chapter one presents the synthetic routes used to prepare C32H 12 and attempts toward synthesizing C40H14 and C46H20. The novel C32H12 is only the second known fullerene fragment that contains more than thirty carbon atoms. It is successfully produced by flash vacuum pyrolysis by either 7,10-bis(2-bromophenyl)benzo[ k]-fluoranthene or 7,10-bis(2,5-dibromophenyl)benzo[k]-fluoranthene. Chapter two outlines a significant improvement in the production of 1,2,5,6-tetraketopyracene, a key intermediate in the synthesis of C30H12. An unreliable and low yield three step synthesis is replaced by a one step high yield conversion of 1,2-diketopyracene to 1,2,5,6-tetraketopyracene via oxidation with benzeneseleninic anhydride. In addition, chapter two discusses an extension of this methodology to include oxidation of benzylic alkenes. This represents a new and unprecedented synthetic transformation of benzylic alkenes to 1,2-diketones.

ISBN

9780599213586

Pages

150

DOI

10.31390/gradschool_disstheses.6817

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