Diazonium 4-(trifluorovinyloxy) Perfluorobutanesulfonyl Benzenesulfonimide Zwitterionic Monomer Synthesis

Author

Isaac D. Addo, East Tennessee State UniversityFollow

Degree Name

MS (Master of Science)

Program

Chemistry

Date of Award

12-2016

Committee Chair or Co-Chairs

Hua Mei

Committee Members

Aleksey Vasiliev, Greg Bishop

Abstract

3-Diazonium- 4-(trifluorovinyloxy) - perfluorobutanesulfonyl benzenesulfonimide zwitterionic monomer (see figure 1) is proposed to be polymerized and further act as a new electrolyte for Polymer exchange membrane fuel cells (PEMFCs). One reason is that, the aromatic trifluorovinyl aryl ether (TFVE) group can easily be homopolymerized to aromatic perfluorocyclobutane (PFCB) polymer. Furthermore, the diazonium moiety in the monomer is expected to covalently attach the electrolyte to the carbon electrodes support. The perfluoroalkyl(aryl) sulfonimide (PFSI) pendant provides good chemical and mechanical stability as well as better proton conductivity. Several multi-step synthetic schemes are designed to obtain such monomer from perfluoroalkyl(aryl) sulfonimide (PFSI). Among them, the purified coupling product 4-OCF₂CF₂Br-3-NO₂-PhSO₂(M) SO₂C₄F₉ from the first approach was successfully completed. The next stages of the work will involve dehalogenation, reduction, and diazotization to achieve the targeting monomer. All the intermediates were characterized by ¹H and ¹⁹F NMR and FT-IR spectroscopy.

Document Type

Thesis - unrestricted

Recommended Citation

Addo, Isaac D., "Diazonium 4-(trifluorovinyloxy) Perfluorobutanesulfonyl Benzenesulfonimide Zwitterionic Monomer Synthesis" (2016). Electronic Theses and Dissertations. Paper 3137. https://dc.etsu.edu/etd/3137

Copyright

Copyright by the authors.