A theoretical study of how C2-substitution affects alkaline stability in imidazolium-based anion exchange membranes

A theoretical study of how C2-substitution affects alkaline stability in imidazolium-based anion... We use density functional theory and investigate the effect on C2-substitution in imidazolium-based anion exchange membranes (AEMs). Here, a C2-unsubstituted 1-ethyl-3-(4-isopropylbenzyl) imidazolium cation (EIIM), a 1-ethyl-2-methyl-3-(4-isopropylbenzyl) imidazolium cation (EMIIM), a 1-ethyl-2-isopropyl-3-(4-isopropylbenzyl) imidazolium cation (EIIIM) and a 1-ethyl-2-phenyl-3-(4-isopropylbenzyl) imidazolium cation (EPhIIm) are prepared. In our previous paper, we suggested that C2-unsubstituted EIIM was quite sensitive to a deprotonation reaction because it was thermodynamically downhill. In the present work, we calculate the alkaline stability of the C2-substituted imidazolium cations and clarify which part is most affected by the C2-substitution. First, in order to investigate the effect on the steric hindrance by each substituent, potential energy curves are described. The effect appears explicitly in the C2-substituted imidazolium cations. Second, the minimum energy paths along the ring-opening and deprotonation reactions are calculated. Finally, we conclude that the alkaline stability is in the order of EMIIM>EIIIM>EPhIIM>EIIM. Furthermore, the order of the alkaline stability is consistent with that of the experiment performed by Lin et al. http://www.deepdyve.com/assets/images/DeepDyve-Logo-lg.png Solid State Ionics Elsevier

A theoretical study of how C2-substitution affects alkaline stability in imidazolium-based anion exchange membranes

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Publisher
Elsevier
Copyright
Copyright © 2015 Elsevier Ltd
ISSN
0167-2738
eISSN
1872-7689
D.O.I.
10.1016/j.ssi.2015.05.006
Publisher site
See Article on Publisher Site

Abstract

We use density functional theory and investigate the effect on C2-substitution in imidazolium-based anion exchange membranes (AEMs). Here, a C2-unsubstituted 1-ethyl-3-(4-isopropylbenzyl) imidazolium cation (EIIM), a 1-ethyl-2-methyl-3-(4-isopropylbenzyl) imidazolium cation (EMIIM), a 1-ethyl-2-isopropyl-3-(4-isopropylbenzyl) imidazolium cation (EIIIM) and a 1-ethyl-2-phenyl-3-(4-isopropylbenzyl) imidazolium cation (EPhIIm) are prepared. In our previous paper, we suggested that C2-unsubstituted EIIM was quite sensitive to a deprotonation reaction because it was thermodynamically downhill. In the present work, we calculate the alkaline stability of the C2-substituted imidazolium cations and clarify which part is most affected by the C2-substitution. First, in order to investigate the effect on the steric hindrance by each substituent, potential energy curves are described. The effect appears explicitly in the C2-substituted imidazolium cations. Second, the minimum energy paths along the ring-opening and deprotonation reactions are calculated. Finally, we conclude that the alkaline stability is in the order of EMIIM>EIIIM>EPhIIM>EIIM. Furthermore, the order of the alkaline stability is consistent with that of the experiment performed by Lin et al.

Journal

Solid State IonicsElsevier

Published: Oct 1, 2015

References

  • Chem. Rev.
    Hickner, Michael A.; Ghassemi, Hossein; Kim, Yu Seung; Einsla, Brian R.; McGrath, James E.

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