Publication Date


Document Type


Committee Members

Eric Fossum (Advisor), David Dolson (Committee Member), Kuppuswamy Arumugam (Committee Member)

Degree Name

Master of Science (MS)


The synthesis of N-heterocycle functionalized triphenylphosphine oxide based PAEs, utilizing 3,5 difluorinated diphenyl sulfone systems was achieved. 3’-Iodo 3,5-difluorodiphenylsulfone was subjected to copper and palladium catalyzed coupling reactions with carbazole, phenothiazine, and indole. The syntheses of 3’-(9-carbazole) 3,5-difluorodiphenylsulfone, 3’-(9-phenothiazine) 3,5-difluorodiphenylsulfone, and 3’-(9-indole) 3,5-difluorodiphenylsulfone were successfully carried out. Copolymers with 4,4’ difluorotriphenylphosphine oxide, as well as 4,4’ dihydroxydiphenyl ether (DPE), as the nucleophilic partner, were prepared via standard nucleophilic aromatic substitution (NAS) polycondensataion reactions. Incorporation of the monomers containing N-heterocycle units was determined by NMR spectroscopy. All polymers displayed sufficient molecular weights (Mn) to allow for films to be cast from THF solution. Polymers in the series displayed excellent thermal stability with 5% weight loss temperatures (Td-5%) above 375 ⁰C, under a nitrogen atmosphere, and relatively high glass transition temperatures (Tg) ranging from 181 ⁰C for the DPS-PTZ based copolymers to 194 ⁰C for the indole-based copolymer.

Page Count


Department or Program

Department of Chemistry

Year Degree Awarded


Included in

Chemistry Commons