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Poly(arylene alkylene)s with pendant N-spirocyclic quaternary ammonium cations for anion exchange membranes

Pham, Thanh Huong LU ; Olsson, Joel LU and Jannasch, Patric LU (2018) In Journal of Materials Chemistry A 6(34). p.16537-16547
Abstract
Aromatic polymers functionalised with cycloaliphatic quaternary ammonium (QA) cations are currently emerging as base stable anion exchange membranes (AEMs) for use in alkaline fuel cells and water electrolyzers. In the present work we have first prepared poly(biphenyl piperidine)s in superacid-mediated polycondensations, and then introduced different N-spirocyclic QA cations via cyclo-quaternisations of the piperidine rings. The resulting polymers and AEMs were free of diaryl ether linkages and benzylic C-H bonds, and showed very high thermal stability and hydroxide ion conductivity. Alkaline testing up to 120 °C implied that the alkaline stability of the spirocyclic cations was limited by distortions of the ring conformations by... (More)
Aromatic polymers functionalised with cycloaliphatic quaternary ammonium (QA) cations are currently emerging as base stable anion exchange membranes (AEMs) for use in alkaline fuel cells and water electrolyzers. In the present work we have first prepared poly(biphenyl piperidine)s in superacid-mediated polycondensations, and then introduced different N-spirocyclic QA cations via cyclo-quaternisations of the piperidine rings. The resulting polymers and AEMs were free of diaryl ether linkages and benzylic C-H bonds, and showed very high thermal stability and hydroxide ion conductivity. Alkaline testing up to 120 °C implied that the alkaline stability of the spirocyclic cations was limited by distortions of the ring conformations by the rigid polymer backbone. As a consequence, the ring directly attached to the backbone degraded significantly faster by Hofmann β-elimination than the pendant ring in the spirocyclic cations. The results provide valuable insights towards the molecular design of highly thermochemically stable AEMs functionalised with N-spirocyclic QA cations. (Less)
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author
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Journal of Materials Chemistry A
volume
6
issue
34
pages
11 pages
publisher
Royal Society of Chemistry
external identifiers
  • scopus:85052705621
ISSN
2050-7488
DOI
10.1039/C8TA04699A
language
English
LU publication?
yes
id
ccd5f0bb-4187-4727-bb58-f585d7f32ae1
date added to LUP
2018-08-01 12:42:01
date last changed
2018-10-04 13:47:27
@article{ccd5f0bb-4187-4727-bb58-f585d7f32ae1,
  abstract     = {Aromatic polymers functionalised with cycloaliphatic quaternary ammonium (QA) cations are currently emerging as base stable anion exchange membranes (AEMs) for use in alkaline fuel cells and water electrolyzers. In the present work we have first prepared poly(biphenyl piperidine)s in superacid-mediated polycondensations, and then introduced different <i>N</i>-spirocyclic QA cations via cyclo-quaternisations of the piperidine rings. The resulting polymers and AEMs were free of diaryl ether linkages and benzylic C-H bonds, and showed very high thermal stability and hydroxide ion conductivity. Alkaline testing up to 120 °C implied that the alkaline stability of the spirocyclic cations was limited by distortions of the ring conformations by the rigid polymer backbone. As a consequence, the ring directly attached to the backbone degraded significantly faster by Hofmann β-elimination than the pendant ring in the spirocyclic cations. The results provide valuable insights towards the molecular design of highly thermochemically stable AEMs functionalised with <i>N</i>-spirocyclic QA cations.},
  author       = {Pham, Thanh Huong and Olsson, Joel and Jannasch, Patric},
  issn         = {2050-7488},
  language     = {eng},
  number       = {34},
  pages        = {16537--16547},
  publisher    = {Royal Society of Chemistry},
  series       = {Journal of Materials Chemistry A},
  title        = {Poly(arylene alkylene)s with pendant <i>N</i>-spirocyclic quaternary ammonium cations for anion exchange membranes},
  url          = {http://dx.doi.org/10.1039/C8TA04699A},
  volume       = {6},
  year         = {2018},
}