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Facile synthesis and polymerization of 2,6-difluoro-2’-sulfobenzophenone for aromatic proton conducting ionomers with pendant sulfobenzoyl groups

Persson Jutemar, Elin LU ; Takamuku, Shogo LU and Jannasch, Patric LU (2010) In Macromolecular Rapid Communications 31(15). p.1348-1353
Abstract
The lithium salt of 2,6-difluoro-2′-sulfobenzophenone was conveniently synthesized in one-pot by reacting 2,6-difluorophenyllithium with 2-sulfobenzoic acid cyclic anhydride in THF at −70 °C whereafter the product crystallized out of solution. A poly(arylene ether) and a poly(arylene sulfide) were prepared by polycondensation reactions to demonstrate the reactivity and efficacy of this new monomer to produce sulfonated high-molecular weight aromatic polymers for fuel cell proton-exchange membranes. This work demonstrated that organolithium chemistry may offer versatile and straightforward pathways to new functional monomers with fluorine atoms activated for nucleophilic aromatic substitution reactions.
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
keywords
polymer electrolyte fuel cell membranes, sulfonated monomers, ionomers, polyaromatics, polyelectrolytes
in
Macromolecular Rapid Communications
volume
31
issue
15
pages
1348 - 1353
publisher
John Wiley & Sons
external identifiers
  • wos:000280944700005
  • scopus:77955321653
ISSN
1022-1336
DOI
10.1002/marc.201000081
language
English
LU publication?
yes
id
6e73b334-7960-467e-95ce-cdc793a69489 (old id 1554110)
date added to LUP
2010-03-11 14:37:35
date last changed
2018-05-29 11:25:08
@article{6e73b334-7960-467e-95ce-cdc793a69489,
  abstract     = {The lithium salt of 2,6-difluoro-2′-sulfobenzophenone was conveniently synthesized in one-pot by reacting 2,6-difluorophenyllithium with 2-sulfobenzoic acid cyclic anhydride in THF at −70 °C whereafter the product crystallized out of solution. A poly(arylene ether) and a poly(arylene sulfide) were prepared by polycondensation reactions to demonstrate the reactivity and efficacy of this new monomer to produce sulfonated high-molecular weight aromatic polymers for fuel cell proton-exchange membranes. This work demonstrated that organolithium chemistry may offer versatile and straightforward pathways to new functional monomers with fluorine atoms activated for nucleophilic aromatic substitution reactions.},
  author       = {Persson Jutemar, Elin and Takamuku, Shogo and Jannasch, Patric},
  issn         = {1022-1336},
  keyword      = {polymer electrolyte fuel cell
membranes,sulfonated monomers,ionomers,polyaromatics,polyelectrolytes},
  language     = {eng},
  number       = {15},
  pages        = {1348--1353},
  publisher    = {John Wiley & Sons},
  series       = {Macromolecular Rapid Communications},
  title        = {Facile synthesis and polymerization of 2,6-difluoro-2’-sulfobenzophenone for aromatic proton conducting ionomers with pendant sulfobenzoyl groups},
  url          = {http://dx.doi.org/10.1002/marc.201000081},
  volume       = {31},
  year         = {2010},
}