Publication Date


Document Type


Committee Members

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

Degree Name

Master of Science (MS)


A difluoro indeno[2,1-c]fluorene monomer was synthesized by a four-step process. The first compound synthesized by a two-step process was 2,5- bis(ethoxycarbonyl)-3,4-di(4-fluorophenyl)cyclopentadienone. The next two compounds synthesized were diethyl 2,3-bis(fluorophenyl)-5-hexylterephthalate and 2,3- bis(fluorophenyl)-5-hexylterephthalic acid. The final step involved an intramolecular Friedel-Crafts acylation of the terephthalic acid derivative to form 3,10-difluoro-5,8- dioxo-5,8-dihydro-6-hexylindeno[2,1-c]fluorene. The difluoro monomer was reacted in a series of nucleophilic aromatic substitution (NAS) polymerization reactions with bisphenol-A in N-methyl-pyrrolidone (NMP) in an attempt to form novel poly(ether ether ketone ketone)s containing the indeno[2,1-c]fluorene structure. Analysis of the product by NMR and TLC showed the reaction was unsuccessful and the difluoro monomer did not undergo significant fluorine displacement. A series of model reactions in NMP and dimethyl sulfoxide (DMSO) also confirmed that the monomer did not undergo fluorine displacement under polymerization conditions. In addition, the synthesis of diethyl 5,6-diphenyl-2,3-bis(2-thienyl)terephthalate and 2,8-dibromo-5,11-bis(4-bromophenyl)-indeno[1,2-b]fluorene-6,12-dione were carried out.

Page Count


Department or Program

Department of Chemistry

Year Degree Awarded


Included in

Chemistry Commons