Publication Date


Document Type


Committee Members

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

Degree Name

Master of Science (MS)


In an ongoing project involving the synthesis of functionalized poly(arylene ether)s that carry pendent phenyl sulfonyl groups, the introduction of an iodo group was desired. The effects of fluorine position on the electrophilic iodination of the 2,4-, 2,6-, and 2,5- and 3,5-isomers of difluorodiphenylsulfone, DFDPS were studied. The relative reactivity, toward EAS, was probed via 13C NMR spectroscopy and verified experimentally by iodination with N-iodosuccinimide. The product mixtures and corresponding structures indicated that intermediate stability did not always correlate to reactivity. Model studies were also conducted on DFDPS isomers that successfully carry in iodo groups in a pendent position.

2,4- and 3,5- Isomers of difluoro-N,N-diphenylbenzene sulfonamide have been synthesized for polymerization by nucleophilic aromatic substitution. Their properties were characterized by 1H, 13C, and 19F NMR spectroscopy and elemental analysis. The 2,4- and 3,5- isomers of difluoro-N,N-diphenylbenzene were polymerized with Bisphenol-A and the resultant polymers were characterized by TGA, DSC, and SEC. The isomers were successfully iodinated with N-iodosuccinimide. Model studies and polymerization reactions on the resultant 3,5-difluoro-N,N-bis(4-iodo)diphenylbenzene sulfonamide were conducted.

Page Count


Department or Program

Department of Chemistry

Year Degree Awarded


Included in

Chemistry Commons