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

Lafitte, Benoit LU and Jannasch, Patric LU (2007) In Journal of Polymer Science. Part A, Polymer Chemistry 45(2). p.269-283
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... (More)
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. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Polymer Science. Part A, Polymer Chemistry
volume
45
issue
2
pages
269 - 283
publisher
John Wiley & Sons
external identifiers
  • wos:000243242700010
  • scopus:33846621065
ISSN
0887-624X
DOI
10.1002/pola.21755
language
English
LU publication?
yes
id
51d1c79b-2d0a-4dc1-b978-abdb4f8f5871 (old id 163598)
date added to LUP
2007-07-13 14:05:37
date last changed
2017-08-27 05:24:46
@article{51d1c79b-2d0a-4dc1-b978-abdb4f8f5871,
  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.},
  author       = {Lafitte, Benoit and Jannasch, Patric},
  issn         = {0887-624X},
  language     = {eng},
  number       = {2},
  pages        = {269--283},
  publisher    = {John Wiley & Sons},
  series       = {Journal of Polymer Science. Part A, Polymer Chemistry},
  title        = {Polysulfone ionomers functionalized with benzoyl(difluoromethylenephosphonic acid) side chains for proton-conducting fuel-cell membranes},
  url          = {http://dx.doi.org/10.1002/pola.21755},
  volume       = {45},
  year         = {2007},
}