N-Spirocyclic quaternary ammonium ionene membranes prepared by polyhydroxylakylation
Mansouri Bakvand, Pegah LU ; Pham, Thanh Huong LU and Jannasch, Patric LU
(2025)
In Journal of Membrane Science
723.
- Abstract
- Anion exchange membranes (AEMs) carrying N-spirocyclic quaternary ammonium cations generally have a high alkaline stability because the unstrained ring conformations of this type of bicyclic cation. Here, we have prepared a series of N-spirocyclic quaternary ammonium ionenes (spiro-ionenes) using a diphenyl-functionalized monomer with a di-N-spiro-isoindolium moiety containing two N-spiro cations. This di-cationic monomer was directly employed in superacid mediated polyhydroxyalkylations with isatin, or alternatively N-methylisatin, and p-terphenyl to obtain ether-free oxindole-containing spiro-ionenes with different ion exchange capacities. AEMs based on the spiro-ionenes reached high ion conductivity, up to... (More)
- Anion exchange membranes (AEMs) carrying N-spirocyclic quaternary ammonium cations generally have a high alkaline stability because the unstrained ring conformations of this type of bicyclic cation. Here, we have prepared a series of N-spirocyclic quaternary ammonium ionenes (spiro-ionenes) using a diphenyl-functionalized monomer with a di-N-spiro-isoindolium moiety containing two N-spiro cations. This di-cationic monomer was directly employed in superacid mediated polyhydroxyalkylations with isatin, or alternatively N-methylisatin, and p-terphenyl to obtain ether-free oxindole-containing spiro-ionenes with different ion exchange capacities. AEMs based on the spiro-ionenes reached high ion conductivity, up to 152 mS cm-1, with no detectable degradation of the N-spiro cations after storage in 1 M aq. NaOH for 720 h at 80 °C. Degradation was however detected after storage in 2 M aq. NaOH at 90 °C. Still, the most stable spiro-ionene AEM displayed an ion loss of merely 3% after 720 h. In conclusion, we demonstrate that highly conductive and alkali-stable spiro-ionenes for AEMs can efficiently be prepared by employing N-spirocyclic monomers in polyhydroxyalkylations. (Less)
Please use this url to cite or link to this publication:
https://lup.lub.lu.se/record/5a8e1a26-1162-4e76-9de1-cb5f1e8630ef
- author
- Mansouri Bakvand, Pegah
LU
; Pham, Thanh Huong
LU
and Jannasch, Patric
LU
- organization
- publishing date
- 2025
- type
- Contribution to journal
- publication status
- published
- subject
- in
- Journal of Membrane Science
- volume
- 723
- article number
- 123922
- publisher
- Elsevier
- external identifiers
-
- scopus:85219663766
- ISSN
- 0376-7388
- DOI
- 10.1016/j.memsci.2025.123922
- language
- English
- LU publication?
- yes
- id
- 5a8e1a26-1162-4e76-9de1-cb5f1e8630ef
- date added to LUP
- 2024-12-24 12:02:20
- date last changed
- 2025-04-04 15:17:30
@article{5a8e1a26-1162-4e76-9de1-cb5f1e8630ef,
abstract = {{Anion exchange membranes (AEMs) carrying N-spirocyclic quaternary ammonium cations generally have a high alkaline stability because the unstrained ring conformations of this type of bicyclic cation. Here, we have prepared a series of N-spirocyclic quaternary ammonium ionenes (spiro-ionenes) using a diphenyl-functionalized monomer with a di-<i>N</i>-spiro-isoindolium moiety containing two <i>N</i>-spiro cations. This di-cationic monomer was directly employed in superacid mediated polyhydroxyalkylations with isatin, or alternatively <i>N</i>-methylisatin, and <i>p</i>-terphenyl to obtain ether-free oxindole-containing spiro-ionenes with different ion exchange capacities. AEMs based on the spiro-ionenes reached high ion conductivity, up to 152 mS cm<sup>-1</sup>, with no detectable degradation of the <i>N</i>-spiro cations after storage in 1 M aq. NaOH for 720 h at 80 °C. Degradation was however detected after storage in 2 M aq. NaOH at 90 °C. Still, the most stable spiro-ionene AEM displayed an ion loss of merely 3% after 720 h. In conclusion, we demonstrate that highly conductive and alkali-stable spiro-ionenes for AEMs can efficiently be prepared by employing <i>N</i>-spirocyclic monomers in polyhydroxyalkylations.}},
author = {{Mansouri Bakvand, Pegah and Pham, Thanh Huong and Jannasch, Patric}},
issn = {{0376-7388}},
language = {{eng}},
publisher = {{Elsevier}},
series = {{Journal of Membrane Science}},
title = {{<i>N</i>-Spirocyclic quaternary ammonium ionene membranes prepared by polyhydroxylakylation}},
url = {{http://dx.doi.org/10.1016/j.memsci.2025.123922}},
doi = {{10.1016/j.memsci.2025.123922}},
volume = {{723}},
year = {{2025}},
}