William Feld (Advisor), Eric Fossum (Committee Member), Kenneth Turnbull (Committee Member)
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.
Department or Program
Department of Chemistry
Year Degree Awarded
Copyright 2017, all rights reserved. My ETD will be available under the "Fair Use" terms of copyright law.