Publication Date


Document Type


Committee Members

William Feld (Advisor), Eric Fossum (Committee Member), Ken Turnbull (Committee Member)

Degree Name

Master of Science (MS)


A series of terephthalate esters was synthesized via a Diels-Alder reaction between 2,5-dicarboethoxy-3,4-diphenylcyclopentadienone and various alkynes in order to study reaction conditions necessary to synthesize poly(indeno[2,1-c]fluorene-5,8-dione)s. Diethyl 2,3-diphenyl-5-butylterephthalate, 1,4-bis(3,4-diphenyl-2,5-di(ethoxycarbonyl) phenyl)butane and N,N,N-tris(3,4-diphenyl-2,5-di(ethoxycarbonyl)phenylmethyl)amine were synthesized and characterized by IR, 1H NMR, 13C NMR, 13C NMR DEPT135 spectroscopies as well as elemental composition. Hydrolysis conditions of the terephthalates using potassium hydroxide were also investigated. It was found that large stoichiometric equivalents of base coupled with reaction times over twenty-four hours afforded only partially hydrolyzed products. The synthesis of 6-butylindeno[2,1-c]fluoren-5,8-dione was successfully carried out by the sulfuric acid catalyzed, intramolecular, Friedel-Crafts cyclization of 5-butyl-2,3-diphenyl terephthalic acid. Full spectroscopic, elemental and melting point characterization is reported.

Page Count


Department or Program

Department of Chemistry

Year Degree Awarded


Included in

Chemistry Commons