Date of Award

1995

Document Type

Dissertation

Degree Name

Doctor of Philosophy (PhD)

Department

Chemistry

First Advisor

William H. Daly

Abstract

Anthracene is a fluorescent molecule that undergoes chemical reactions as a Diels-Alder diene. Incorporation of the anthracene nucleus into a polymer system imparts upon it the characteristics of anthracene. This work in concerned with the synthesis of a suitable 2,3,6,7-anthracenetetracarboxylic acid based monomer. The monomer is then polymerized and the resultant polymer is crosslinked in a Diels-Alder reaction. The synthesis of 2,3,6,7-anthracene derivatives is underdeveloped. The difficulty in the synthesis of these compounds has probably precluded their development. Herein is described the synthesis of 2,3,6,7-anthracenetetracarboxylic acid in three simple steps inexpensively and in high yield. Older methods required more steps and costly reagents. The solubility of monomer precursors was generally quite low causing great difficulty. An ester/acid chloride monomer was developed that was soluble, purifiable and polymerizable. Polymers derived from this monomer were thermally stable, fluorescent, and active as Diels-Alder dienes. The polymeric Diels-Alder reaction was successful with N-phenylmaleimide leading to the desired polymeric adduct. Crosslinking and concomitant formation of an intractable network was observed when a difunctional maleimide was used in the reaction.

Pages

99

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