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Title: Design and Synthesis of Imidazolium-Mediated Tröger’s Base-Containing Ionene Polymers for Advanced CO 2 Separation Membranes

Abstract

It is highly desirable to integrate the CO 2 solubility benefits of ionic liquids (ILs) in polymeric membrane systems for effective CO 2 separations. Herein, we are exclusively exploring a series of four novel imidazolium-mediated Tröger’s base (TB)-containing ionene polymers for enhanced CO 2 separation. The two diimidazole-functionalized Tröger’s base monomers synthesized from “ortho”- and “para”-substituted imidazole anilines were polymerized with equimolar amounts of two different aromatic and aliphatic comonomers (α,α'-dichloro- p-xylene and 1,10-dibromodecane, respectively) via Menshutkin reactions to obtain four respective ionene polymers ([Im-TB( o&p)-Xy][Cl] and ([Im-TB( o&p)-C 10][Br], respectively). The resulting ionene polymers having halide anions were exchanged with [Tf 2N] - anions, yielding a novel Tröger’s base material [Im-TB(x)-R][Tf 2N] or “Im-TB-Ionenes”. The structural and physical properties as well as the gas separation behaviors of the copolymers of aromatic and aliphatic Im-TB-Ionenes have been extensively investigated with respect to the regiochemistry of imidazolium groups at the ortho and para positions of the TB unit. The imidazolium-mediated TB-Ionenes showed high CO 2 solubility and hence an excellent CO 2/CH 4 permselectivity of 82.5. The Im-TB-Ionenes also displayed good thermal and mechanical stabilities.

Authors:
ORCiD logo [1];  [1]; ORCiD logo [1];  [2]
  1. Department of Chemical &, Biological Engineering, University of Alabama, Tuscaloosa, Alabama 35487-0203, United States
  2. NASA Marshall Space Flight Center, Huntsville, Alabama 35812, United States
Publication Date:
Research Org.:
Univ. of Alabama, Tuscaloosa, AL (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES); National Science Foundation (NSF)
OSTI Identifier:
1494862
Alternate Identifier(s):
OSTI ID: 1508826
Grant/Contract Number:  
SC0018181; CHE-1726812; 80MSFC18M0041
Resource Type:
Journal Article: Published Article
Journal Name:
ACS Omega
Additional Journal Information:
Journal Name: ACS Omega Journal Volume: 4 Journal Issue: 2; Journal ID: ISSN 2470-1343
Publisher:
American Chemical Society
Country of Publication:
United States
Language:
English
Subject:
37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats

Kammakakam, Irshad, O’Harra, Kathryn E., Bara, Jason E., and Jackson, Enrique M. Design and Synthesis of Imidazolium-Mediated Tröger’s Base-Containing Ionene Polymers for Advanced CO 2 Separation Membranes. United States: N. p., 2019. Web. doi:10.1021/acsomega.8b03700.
Kammakakam, Irshad, O’Harra, Kathryn E., Bara, Jason E., & Jackson, Enrique M. Design and Synthesis of Imidazolium-Mediated Tröger’s Base-Containing Ionene Polymers for Advanced CO 2 Separation Membranes. United States. https://doi.org/10.1021/acsomega.8b03700
Kammakakam, Irshad, O’Harra, Kathryn E., Bara, Jason E., and Jackson, Enrique M. Fri . "Design and Synthesis of Imidazolium-Mediated Tröger’s Base-Containing Ionene Polymers for Advanced CO 2 Separation Membranes". United States. https://doi.org/10.1021/acsomega.8b03700.
@article{osti_1494862,
title = {Design and Synthesis of Imidazolium-Mediated Tröger’s Base-Containing Ionene Polymers for Advanced CO 2 Separation Membranes},
author = {Kammakakam, Irshad and O’Harra, Kathryn E. and Bara, Jason E. and Jackson, Enrique M.},
abstractNote = {It is highly desirable to integrate the CO2 solubility benefits of ionic liquids (ILs) in polymeric membrane systems for effective CO2 separations. Herein, we are exclusively exploring a series of four novel imidazolium-mediated Tröger’s base (TB)-containing ionene polymers for enhanced CO2 separation. The two diimidazole-functionalized Tröger’s base monomers synthesized from “ortho”- and “para”-substituted imidazole anilines were polymerized with equimolar amounts of two different aromatic and aliphatic comonomers (α,α'-dichloro-p-xylene and 1,10-dibromodecane, respectively) via Menshutkin reactions to obtain four respective ionene polymers ([Im-TB(o&p)-Xy][Cl] and ([Im-TB(o&p)-C10][Br], respectively). The resulting ionene polymers having halide anions were exchanged with [Tf2N]- anions, yielding a novel Tröger’s base material [Im-TB(x)-R][Tf2N] or “Im-TB-Ionenes”. The structural and physical properties as well as the gas separation behaviors of the copolymers of aromatic and aliphatic Im-TB-Ionenes have been extensively investigated with respect to the regiochemistry of imidazolium groups at the ortho and para positions of the TB unit. The imidazolium-mediated TB-Ionenes showed high CO2 solubility and hence an excellent CO2/CH4 permselectivity of 82.5. The Im-TB-Ionenes also displayed good thermal and mechanical stabilities.},
doi = {10.1021/acsomega.8b03700},
url = {https://www.osti.gov/biblio/1494862}, journal = {ACS Omega},
issn = {2470-1343},
number = 2,
volume = 4,
place = {United States},
year = {2019},
month = {2}
}

Journal Article:
Free Publicly Available Full Text
Publisher's Version of Record at https://doi.org/10.1021/acsomega.8b03700

Citation Metrics:
Cited by: 6 works
Citation information provided by
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Figures / Tables:

Figure 1 Figure 1: Tröger’s base-containing diimidazole monomers used in this study.

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Works referencing / citing this record:

Synthesis and Performance of 6FDA-Based Polyimide-Ionenes and Composites with Ionic Liquids as Gas Separation Membranes
journal, July 2019


Synthesis and Performance of 6FDA-Based Polyimide-Ionenes and Composites with Ionic Liquids as Gas Separation Membranes
journal, July 2019


Synthesised spirobichroman‐based polyimide functionalized by pyridine: Effects of substituent position on gas separation and thermal properties
journal, December 2019


Recent Advances in the Design of Ionenes: Toward Convergence with High‐Performance Polymers
journal, May 2019


Understanding the effects of backbone chemistry and anion type on the structure and thermal behaviors of imidazolium polyimide‐ionenes
journal, May 2019