Polysulfone ionomers functionalized with benzoyl(difluoromethylenephosphonic acid) side chains for proton-conducting fuel-cell membranes

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Abstract

Polysulfones carrying benzoyl(difluoromethylenephosphonic acid) side chains were prepared and investigated for use as proton-conducting fuel-cell membranes. In the first step, polysulfones were lithiated and reacted with methyl iodobenzoates to prepare p- and o-iodobenzoyl polysulfones. Next, the phosphonated polysulfones were prepared via CuBr-mediated cross-coupling reactions between the iodinated polymer and [(diethoxyphosphinyl)difluoromethyl]zinc bromide. Finally, dealkylation with bromotrimethylsilane afforded highly acidic -CF2-PO3H2 derivatives. The replacement of the iodine atoms by -CF2-PO3Et2 units was almost quantitative in the case of o-iodobenzoyl polysulfone. Membranes based on ionomers having 0.90 mmol of phosphonic acid units/g of dry polymer took up 6 wt % water when immersed at room temperature, and conductivities up to 5 mS cm-1 at 100 °C were recorded. This level of conductivity was comparable to that reached by a membrane based on a sulfonated polysulfone having 0.86 mmol of sulfonic acid/g of dry polymer. Thermogravimetry revealed that the aryl-CF2-PO3H2 arrangement decomposed at approximately 230 °C via cleavage of the C-P bond.

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  • Chemical Sciences
Original languageEnglish
Pages (from-to)269-283
JournalJournal of Polymer Science. Part A, Polymer Chemistry
Volume45
Issue number2
Publication statusPublished - 2007
Publication categoryResearch
Peer-reviewedYes

Bibliographic note

The information about affiliations in this record was updated in December 2015. The record was previously connected to the following departments: Polymer and Materials Chemistry (LTH) (011001041)