Toward controlled functional sequencing and hierarchical structuring in imidazolium ionenes

O'Harra, Kathryn E.; Bara, Jason E.

doi:10.1002/pi.6109

Toward controlled functional sequencing and hierarchical structuring in imidazolium ionenes

Journal Article · Mon Aug 31 00:00:00 EDT 2020 · Polymer International

DOI:https://doi.org/10.1002/pi.6109· OSTI ID:1830614

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Univ. of Alabama, Tuscaloosa, AL (United States); University of Alabama
Univ. of Alabama, Tuscaloosa, AL (United States)

This focused mini-review highlights recent advances related to the design and applications of imidazolium ionenes and forward-looking perspectives. Creative strategies which employ established synthetic approaches and utilize the modularity of the imidazole moiety unlock great potential for tailoring both functional and structural features arising from precise spacing of ionic groups within the polymer backbone. Here, as imidazolium ionenes draw more interest, increased sophistication of chemical modifications and material processing is occurring, with a corresponding shift toward more demanding applications. Synthetic routes for placement and sequencing of ionic content are discussed, in addition to recent approaches to control structure and self-assembly or tune behaviors of imidazolium ionenes and composites.

View Accepted Manuscript (DOE)

Research Organization:: Univ. of Alabama, Tuscaloosa, AL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: SC0018181

OSTI ID:: 1830614

Journal Information:: Polymer International, Journal Name: Polymer International Journal Issue: 7 Vol. 70; ISSN 0959-8103

Publisher:: Society of Chemical IndustryCopyright Statement

Country of Publication:: United States

Language:: English

References (85)

Modified Aliphatic Ionenes. Influence of Charge Density and Length of the Chains on Complex Formation with Poly(methacrylic acid) Zelikin, Alexander N.; Akritskaya, Natalia I.; Izumrudov, Vladimir A. Macromolecular Chemistry and Physics, Vol. 202, Issue 15 https://doi.org/10.1002/1521-3935(20011001)202:15<3018::AID-MACP3018>3.0.CO;2-7	journal	October 2001
Imidazolium Polyesters: Structure-Property Relationships in Thermal Behavior, Ionic Conductivity, and Morphology Lee, Minjae; Choi, U. Hyeok; Salas-de la Cruz, David Advanced Functional Materials, Vol. 21, Issue 4 https://doi.org/10.1002/adfm.201001878	journal	December 2010
Selective plasticization of the ionic domains in a segmented thermoplastic ionene cationomer Venkateshwaran, L. N.; Leir, C. E.; Wilkes, G. L. Journal of Applied Polymer Science, Vol. 43, Issue 5 https://doi.org/10.1002/app.1991.070430513	journal	September 1991
Ueber Glyoxalin und seine Homologe Radzisewski, Br. Berichte der deutschen chemischen Gesellschaft, Vol. 15, Issue 2 https://doi.org/10.1002/cber.188201502245	journal	July 1882
Valorization of Plastic Wastes for the Synthesis of Imidazolium‐Based Self‐Supported Elastomeric Ionenes Demarteau, Jeremy; O'Harra, Kathryn E.; Bara, Jason E. ChemSusChem, Vol. 13, Issue 12 https://doi.org/10.1002/cssc.202000505	journal	May 2020
Synthesis of π-Expanded Azole-Fused Imidazo[1,2- a ]pyridine Derivatives and their Photophysical Properties: Synthesis of π-Expanded Azole-Fused Imidazo[1,2- a ]pyridine Derivatives and their Photophysical Properties Nandwana, Nitesh Kumar; Dhiman, Shiv; Shinde, Vikki N. European Journal of Organic Chemistry, Vol. 2020, Issue 17 https://doi.org/10.1002/ejoc.202000236	journal	April 2020
Synthesis of New Bis-imidazole Derivatives Jasiński, Marcin; Mlostoń, Grzegorz; Mucha, Paulina Helvetica Chimica Acta, Vol. 90, Issue 9 https://doi.org/10.1002/hlca.200790186	journal	September 2007
A New Sustainable Strategy for Synthesis of Novel Series of Bis-imidazole and Bis-1,3-thiazine Derivatives: An Eco-friendly Synthesis of Novel Series of Bis-heterocyclic Compounds Arafa, Wael A. A.; Faty, Rasha A. M.; Mourad, Asmaa K. Journal of Heterocyclic Chemistry, Vol. 55, Issue 8 https://doi.org/10.1002/jhet.3221	journal	June 2018
Ueber die Einwirkung des Ammoniaks auf Glyoxal Debus, Heinrich Annalen der Chemie und Pharmacie, Vol. 107, Issue 2 https://doi.org/10.1002/jlac.18581070209	journal	January 1858
Structure-Property Relationships of Water-Soluble Ammonium-Ionene Copolymers Tamami, Mana; Salas-de la Cruz, David; Winey, Karen I. Macromolecular Chemistry and Physics, Vol. 213, Issue 9 https://doi.org/10.1002/macp.201200047	journal	April 2012
Cationic Main-Chain Polyelectrolytes with Pyridinium-Based p -Phenylenevinylene Units and Their Aggregation-Induced Gelation Samanta, Suman Kalyan; Scherf, Ullrich Macromolecular Chemistry and Physics, Vol. 218, Issue 1 https://doi.org/10.1002/macp.201600374	journal	September 2016
Main-Chain Polyimidazolium Polymers by One-Pot Synthesis and Application as Nitrogen-Doped Carbon Precursors Grygiel, Konrad; Kirchhecker, Sarah; Gong, Jiang Macromolecular Chemistry and Physics, Vol. 218, Issue 18 https://doi.org/10.1002/macp.201600586	journal	March 2017
Influence of Counterion on Thermal, Viscoelastic, and Ion Conductive Properties of Phosphonium Ionenes Abdulahad, Asem I.; Jangu, Chainika; Hemp, Sean T. Macromolecular Symposia, Vol. 342, Issue 1 https://doi.org/10.1002/masy.201400030	journal	August 2014
Self‐healing imidazolium‐based ionene‐polyamide membranes: an experimental study on physical and gas transport properties Kammakakam, Irshad; O'Harra, Kathryn E.; Dennis, Grayson P. Polymer International, Vol. 68, Issue 6 https://doi.org/10.1002/pi.5802	journal	March 2019
Understanding the effects of backbone chemistry and anion type on the structure and thermal behaviors of imidazolium polyimide‐ionenes O'Harra, Kathryn E.; Kammakakam, Irshad; Bara, Jason E. Polymer International, Vol. 68, Issue 9 https://doi.org/10.1002/pi.5825	journal	May 2019
Synthesis and characterization of poly(pyridinium salt)s with organic counterion exhibiting both lyotropic liquid-crystalline and light-emitting properties Bhowmik, Pradip K.; Burchett, Ronald A.; Han, Haesook Journal of Polymer Science Part A: Polymer Chemistry, Vol. 39, Issue 16 https://doi.org/10.1002/pola.1248	journal	January 2001
Preparation of main-chain imidazolium-functionalized amphiphilic block copolymers through combination of condensation polymerization and nitroxide-mediated free radical polymerization and their micelle study Li, Xue; Ni, Xufeng; Liang, Zhenhua Journal of Polymer Science Part A: Polymer Chemistry, Vol. 50, Issue 10 https://doi.org/10.1002/pola.25978	journal	February 2012
Synthesis and characterization of polymeric ionic liquid poly(imidazolium chloride-1,3-diylbutane-1,4-diyl) Amarasekara, Ananda S.; Shanbhag, Preethi Polymer Bulletin, Vol. 67, Issue 4 https://doi.org/10.1007/s00289-010-0413-8	journal	November 2010
Synthesis and characterization of branched polymeric ionic liquids with imidazolium chloride segments Amarasekara, Ananda S.; Callis, Brandon; Wiredu, Bernard Polymer Bulletin, Vol. 68, Issue 4 https://doi.org/10.1007/s00289-011-0578-9	journal	July 2011
Copper-catalyzed Ullmann reaction for the synthesis of fused hexacyclic heterocycles containing naphthyridine, acridine, and pyrazole (imidazole) moieties Ma, Yong-Gang; Qiang, Wen-Wen; Li, Chao Monatshefte für Chemie - Chemical Monthly, Vol. 147, Issue 7 https://doi.org/10.1007/s00706-015-1625-2	journal	January 2016
Acidic ionic liquid polymers: poly(bis-imidazolium-p-phenylenesulfonic acid) and applications as catalysts in the preparation of 1-amidoalkyl-2-naphthols Amarasekara, Ananda S.; Nguyen, Jennifer; Razzaq, Ashfaqur Journal of Polymer Research, Vol. 24, Issue 3 https://doi.org/10.1007/s10965-017-1216-5	journal	March 2017
Combined isocyanide-based multi-component Ullmann-type reaction: an efficient access to novel nitrogen-containing pentacyclic compounds Dianat, Shima; Mahdavi, Mohammad; Moghimi, Setareh Molecular Diversity, Vol. 19, Issue 4 https://doi.org/10.1007/s11030-015-9622-2	journal	August 2015
Cationic Polymers Bearing Quaternary Ammonium Groups-Catalyzed CO2 Fixation with Epoxides Tiffner, Maximilian; Häring, Marleen; Díaz, David Díaz Topics in Catalysis, Vol. 61, Issue 15-17 https://doi.org/10.1007/s11244-018-0996-0	journal	May 2018
An imidazolium-based ionene blended with crosslinked PEO as a novel polymer membrane for selective CO2 separation Kammakakam, Irshad; Rao, Anil H. N.; Yoon, Hee Wook Macromolecular Research, Vol. 22, Issue 8 https://doi.org/10.1007/s13233-014-2125-7	journal	August 2014
Preparation and characterization of imidazolium-PEO-based Ionene/PVDF(HFP)/LiTFSI as a novel Gel polymer electrolyte Thankamony, Roshni Lilly; Chu, Hodong; Lim, Sanghyun Macromolecular Research, Vol. 23, Issue 1 https://doi.org/10.1007/s13233-015-3001-9	journal	December 2014
Structure-property behaviour of segmented poly (tetramethylene oxide)-based bipyridinium ionene elastomers Feng, Daan; Wilkes, Garth L.; Lee, Bin Polymer, Vol. 33, Issue 3 https://doi.org/10.1016/0032-3861(92)90729-G	journal	January 1992
Ion-chromatographic selectivity of polyelectrolyte sorbents based on some aliphatic and aromatic ionenes Pirogov, A. V.; Krokhin, O. V.; Platonov, M. M. Journal of Chromatography A, Vol. 884, Issue 1-2 https://doi.org/10.1016/S0021-9673(00)00273-9	journal	July 2000
Novel polyimide ionene: synthesis and characterization of polyimides containing aromatic bipyridinium salt Xuehui, Sun; Yu-kun, Yang; Fengcai, Lu Polymer, Vol. 38, Issue 18 https://doi.org/10.1016/S0032-3861(96)01059-2	journal	September 1997
An efficient copper-catalyzed coupling of aryl halides with imidazoles Kiyomori, Ayumu; Marcoux, Jean-François; Buchwald, Stephen L. Tetrahedron Letters, Vol. 40, Issue 14 https://doi.org/10.1016/S0040-4039(99)00291-9	journal	April 1999
Main-chain imidazolium oligomer material as a selective biomimetic antimicrobial agent Liu, Lihong; Huang, Yuan; Riduan, Siti Nurhanna Biomaterials, Vol. 33, Issue 33 https://doi.org/10.1016/j.biomaterials.2012.08.006	journal	November 2012
Highly potent antimicrobial polyionenes with rapid killing kinetics, skin biocompatibility and in vivo bactericidal activity Liu, Shaoqiong; Ono, Robert J.; Wu, Hong Biomaterials, Vol. 127 https://doi.org/10.1016/j.biomaterials.2017.02.027	journal	May 2017
Main-chain imidazolium polymer membranes for CO2 separations: An initial study of a new ionic liquid-inspired platform Carlisle, Trevor K.; Bara, Jason E.; Lafrate, Andrew L. Journal of Membrane Science, Vol. 359, Issue 1-2 https://doi.org/10.1016/j.memsci.2009.10.022	journal	September 2010
Alkaline fuel cell membranes from xylylene block ionenes Lee, Kyung Min; Wycisk, Ryszard; Litt, Morton Journal of Membrane Science, Vol. 383, Issue 1-2 https://doi.org/10.1016/j.memsci.2011.08.062	journal	November 2011
Synthesis, structure, thermal and mechanical properties of nanocomposites based on linear polymers and layered silicates modified by polymeric quaternary ammonium salts (ionenes) Burmistr, Michail V.; Sukhyy, Kostyantyn M.; Shilov, Valery V. Polymer, Vol. 46, Issue 26 https://doi.org/10.1016/j.polymer.2005.10.094	journal	December 2005
Ionene segmented block copolymers containing imidazolium cations: Structure–property relationships as a function of hard segment content Williams, Sharlene R.; Salas-de la Cruz, David; Winey, Karen I. Polymer, Vol. 51, Issue 6 https://doi.org/10.1016/j.polymer.2009.06.051	journal	March 2010
Imidazole- and imidazolium-containing polymers for biology and material science applications Anderson, Emily B.; Long, Timothy E. Polymer, Vol. 51, Issue 12 https://doi.org/10.1016/j.polymer.2010.02.006	journal	May 2010
Segmented imidazolium ionenes: Solution rheology, thermomechanical properties, and electrospinning Schreiner, Christian; Bridge, Alexander T.; Hunley, Matthew T. Polymer, Vol. 114 https://doi.org/10.1016/j.polymer.2017.03.003	journal	April 2017
Recent advances in the synthesis and structure–property relationships of ammonium ionenes Williams, Sharlene R.; Long, Timothy E. Progress in Polymer Science, Vol. 34, Issue 8 https://doi.org/10.1016/j.progpolymsci.2009.04.004	journal	August 2009
Triazole-based ionene exhibiting tunable structure and ionic conductivity obtained via cycloaddition reaction: A new polyelectrolyte for electrochromic devices Puguan, John Marc C.; Boton, Lilian B.; Kim, Hern Solar Energy Materials and Solar Cells, Vol. 188 https://doi.org/10.1016/j.solmat.2018.09.009	journal	December 2018
Cu2O-catalyzed Ullmann-type reaction of vinyl bromides with imidazole and benzimidazole Shen, Guodong; Lv, Xin; Qian, Weixing Tetrahedron Letters, Vol. 49, Issue 29-30 https://doi.org/10.1016/j.tetlet.2008.04.163	journal	July 2008
Ionic Polyimides: Hybrid Polymer Architectures and Composites with Ionic Liquids for Advanced Gas Separation Membranes Mittenthal, Max S.; Flowers, Brian S.; Bara, Jason E. Industrial & Engineering Chemistry Research, Vol. 56, Issue 17 https://doi.org/10.1021/acs.iecr.7b00462	journal	April 2017
Heterogenization of a Green Homogeneous Catalyst: Synthesis and Characterization of Imidazolium Ionene/Br ^– Cl ^– @SiO ₂ as an Efficient Catalyst for the Cycloaddition of CO ₂ with Epoxides Akbari, Zahra; Ghiaci, Mehran Industrial & Engineering Chemistry Research, Vol. 56, Issue 32 https://doi.org/10.1021/acs.iecr.7b02803	journal	August 2017
Upcycling Poly(ethylene terephthalate) Refuse to Advanced Therapeutics for the Treatment of Nosocomial and Mycobacterial Infections Tan, Jeremy P. K.; Tan, Jason; Park, Nathanial Macromolecules, Vol. 52, Issue 20 https://doi.org/10.1021/acs.macromol.9b01333	journal	October 2019
Design and Synthesis of Imidazolium-Mediated Tröger’s Base-Containing Ionene Polymers for Advanced CO ₂ Separation Membranes Kammakakam, Irshad; O’Harra, Kathryn E.; Bara, Jason E. ACS Omega, Vol. 4, Issue 2 https://doi.org/10.1021/acsomega.8b03700	journal	February 2019
Electronic Structure and Conformational Properties of Polybenzimidazole-Based Ionenes—A Density Functional Theory Investigation Mokhtari, Mehrdad; Eslamibidgoli, Mohammad Javad; Eikerling, Michael H. ACS Omega, Vol. 5, Issue 3 https://doi.org/10.1021/acsomega.9b03116	journal	January 2020
Linear Tricationic Room-Temperature Ionic Liquids: Synthesis, Physiochemical Properties, and Electrowetting Properties Wanigasekara, Eranda; Zhang, Xiaotong; Nanayakkara, Yasith ACS Applied Materials & Interfaces, Vol. 1, Issue 10 https://doi.org/10.1021/am900519j	journal	September 2009
Recognition and Selective Binding of DNA by Ionenes of Different Charge Density Trukhanova, Elizabeth S.; Izumrudov, Vladimir A.; Litmanovich, Andrey A. Biomacromolecules, Vol. 6, Issue 6 https://doi.org/10.1021/bm050536i	journal	October 2005
Versatile and Scalable Method for Producing N -Functionalized Imidazoles Bara, Jason E. Industrial & Engineering Chemistry Research, Vol. 50, Issue 24 https://doi.org/10.1021/ie102535c	journal	December 2011
Synthesis of 1,2-Dialkyl-, 1,4(5)-Dialkyl-, and 1,2,4(5)-Trialkylimidazoles via a One-Pot Method Hindman, Michelle S.; Stanton, Alexander D.; Irvin, A. Christopher Industrial & Engineering Chemistry Research, Vol. 52, Issue 34 https://doi.org/10.1021/ie401861b	journal	August 2013
Assembly and Post-Modification of a Metal–Organic Nanotube for Highly Efficient Catalysis Kong, Guo-Qiang; Ou, Sha; Zou, Chao Journal of the American Chemical Society, Vol. 134, Issue 48 https://doi.org/10.1021/ja309158a	journal	November 2012
N -Spirocyclic Quaternary Ammonium Ionenes for Anion-Exchange Membranes Pham, Thanh Huong; Olsson, Joel S.; Jannasch, Patric Journal of the American Chemical Society, Vol. 139, Issue 8 https://doi.org/10.1021/jacs.6b12944	journal	February 2017
Copper-Catalyzed N-Arylation of Imidazoles and Benzimidazoles Altman, Ryan A.; Koval, Erica D.; Buchwald, Stephen L. The Journal of Organic Chemistry, Vol. 72, Issue 16 https://doi.org/10.1021/jo070807a	journal	July 2007
Interplay of Ion-Specific and Charge-Density Effects in Aqueous Solutions of Weakly Charged Ionenes as Revealed by Electric-Transport Measurements Lukšič, Miha; Hribar-Lee, Barbara; Vlachy, Vojko The Journal of Physical Chemistry B, Vol. 114, Issue 32 https://doi.org/10.1021/jp105301m	journal	July 2010
Conductance and Counterion Activity of Ionene Solutions ^† Nagaya, Jiro; Minakata, Akira; Tanioka, Akihiko Langmuir, Vol. 15, Issue 12 https://doi.org/10.1021/la981190i	journal	June 1999
Polymerized Ionic Liquids via Hydroboration Polymerization as Single Ion Conductive Polymer Electrolytes Matsumi, Noriyoshi; Sugai, Kazunori; Miyake, Masufumi Macromolecules, Vol. 39, Issue 20 https://doi.org/10.1021/ma060472j	journal	October 2006
Highly Efficient Transfer of Amino Groups to Imidazolium Entities for Polymer Coupling and Cross-Linking Krannig, Kai-Steffen; Esposito, Davide; Antonietti, Markus Macromolecules, Vol. 47, Issue 7 https://doi.org/10.1021/ma500269k	journal	March 2014
Synthesis and Characterization of Well-Defined 12,12-Ammonium Ionenes: Evaluating Mechanical Properties as a Function of Molecular Weight Williams, Sharlene R.; Borgerding, Erika M.; Layman, John M. Macromolecules, Vol. 41, Issue 14 https://doi.org/10.1021/ma8006152	journal	July 2008
Hydrogels Based on Surfactant-Free Ionene Polymers with N,N′ -( p -Phenylene)dibenzamide Linkages Misawa, Yoshihiro; Koumura, Nagatoshi; Matsumoto, Hajime Macromolecules, Vol. 41, Issue 22 https://doi.org/10.1021/ma801350k	journal	November 2008
Phenyleneethynylene- and Thienyleneethynylene-Based π-Conjugated Polymers with Imidazolium Units in the Main Chain Toba, Masaya; Nakashima, Takuya; Kawai, Tsuyoshi Macromolecules, Vol. 42, Issue 21 https://doi.org/10.1021/ma901511d	journal	November 2009
Charge-Transfer Reinforced Folding of Novel Ionenes De, Swati; Ramakrishnan, S. Macromolecules, Vol. 42, Issue 22 https://doi.org/10.1021/ma901954x	journal	November 2009
Hydroxide-Stable Ionenes Wright, Andrew G.; Holdcroft, Steven ACS Macro Letters, Vol. 3, Issue 5 https://doi.org/10.1021/mz500168d	journal	April 2014
Structurally Defined Imidazolium-Type Ionic Oligomers as Soluble/Solid Support for Peptide Synthesis He, Xun; Chan, Tak Hang Organic Letters, Vol. 9, Issue 14 https://doi.org/10.1021/ol0708875	journal	June 2007
Shape-Controllable Formation of Poly-imidazolium Salts for Stable Palladium N-Heterocyclic Carbene Polymers Zhao, Huaixia; Li, Liuyi; Wang, Yangxin Scientific Reports, Vol. 4, Issue 1 https://doi.org/10.1038/srep05478	journal	June 2014
Coordination polymers built from 1,4-bis(imidazol-1-ylmethyl)benzene: from crystalline to amorphous Adarsh, N. N.; Novio, Fernando; Ruiz-Molina, Daniel Dalton Transactions, Vol. 45, Issue 28 https://doi.org/10.1039/C6DT01157H	journal	January 2016
Hexamethyl-p-terphenyl poly(benzimidazolium): a universal hydroxide-conducting polymer for energy conversion devices Wright, Andrew G.; Fan, Jiantao; Britton, Benjamin Energy & Environmental Science, Vol. 9, Issue 6 https://doi.org/10.1039/C6EE00656F	journal	January 2016
Aromatic ionene topology and counterion-tuned gelation of acidic aqueous solutions Bachl, Jürgen; Bertran, Oscar; Mayr, Judith Soft Matter, Vol. 13, Issue 16 https://doi.org/10.1039/C7SM00234C	journal	January 2017
pH-Degradable imidazolium oligomers as antimicrobial materials with tuneable loss of activity Yuan, Yuan; Lim, Diane S. W.; Wu, Hong Biomaterials Science, Vol. 7, Issue 6 https://doi.org/10.1039/C8BM01683F	journal	January 2019
The multicomponent Debus–Radziszewski reaction in macromolecular chemistry Saxer, S.; Marestin, C.; Mercier, R. Polymer Chemistry, Vol. 9, Issue 15 https://doi.org/10.1039/C8PY00173A	journal	January 2018
Antibacterial activity of cationic polymers: side-chain or main-chain type? Guo, Jiangna; Qin, Jing; Ren, Yongyuan Polymer Chemistry, Vol. 9, Issue 37 https://doi.org/10.1039/C8PY00665B	journal	January 2018
Electrostatic trapping of polysulfides enabled by imidazolium-based ionic polymers for high-energy-density lithium–sulfur batteries Cheng, Zhibin; Pan, Hui; Xiao, Zhubing Journal of Materials Chemistry A, Vol. 6, Issue 17 https://doi.org/10.1039/C8TA01298A	journal	January 2018
l-Proline promoted Ullmann-type reaction of vinyl bromides with imidazoles in ionic liquids Wang, Zhiming; Bao, Weiliang; Jiang, Yong Chemical Communications, Issue 22 https://doi.org/10.1039/b501628b	journal	January 2005
Microwave-assisted synthesis of imidazolium ionenes and their application as humidity absorbers Erdmenger, Tina; Perevyazko, Igor; Vitz, Jürgen Journal of Materials Chemistry, Vol. 20, Issue 18 https://doi.org/10.1039/b921525e	journal	January 2010
Aqueous solutions of ionenes: interactions and counterion specific effects as seen by neutron scattering Malikova, Natalie; Čebašek, Sašo; Glenisson, Vincent Physical Chemistry Chemical Physics, Vol. 14, Issue 37 https://doi.org/10.1039/c2cp41859b	journal	January 2012
Phosphonium ionenes from well-defined step-growth polymerization: thermal and melt rheological properties Hemp, Sean T.; Zhang, Musan; Tamami, Mana Polymer Chemistry, Vol. 4, Issue 12 https://doi.org/10.1039/c3py00365e	journal	January 2013
Syntheses of polyalkylated imidazoles Evjen, Sigvart; Fiksdahl, Anne Synthetic Communications, Vol. 47, Issue 15 https://doi.org/10.1080/00397911.2017.1330416	journal	June 2017
Designing Imidazole-Based Ionic Liquids and Ionic Liquid Monomers for Emerging Technologies Green, Matthew D.; Long, Timothy E. Polymer Reviews, Vol. 49, Issue 4 https://doi.org/10.1080/15583720903288914	journal	October 2009
MATERIALS SCIENCE: A Unique Platform for Materials Design Lodge, T. P. Science, Vol. 321, Issue 5885 https://doi.org/10.1126/science.1159652	journal	July 2008
Synthesis and properties of a new family of phosphorus- and nitrogen-containing ionenes Mikhailenko, V. L.; Kizhnyaev, V. N.; Verkhoturova, S. I. Doklady Chemistry, Vol. 465, Issue 2 https://doi.org/10.1134/S0012500815120034	journal	December 2015
Synthesis and properties of azole-containing ionenes Kizhnyaev, V. N.; Krakhotkina, E. A.; Petrova, T. L. Polymer Science Series B, Vol. 53, Issue 3-4 https://doi.org/10.1134/S1560090411030043	journal	April 2011
Poly(ionic liquid)-based polyurethanes having imidazolium, ammonium, morpholinium or pyrrolidinium cations Morozova, Sofia M.; Shaplov, Alexander S.; Lozinskaya, Elena I. High Performance Polymers, Vol. 29, Issue 6 https://doi.org/10.1177/0954008317701551	journal	April 2017
Synthesis and application of imidazole derivatives: Preparation of various diketones from 1,n-bis(1-methyl-1H-imidazol-2-yl)alkane-1,n-diones. Hayakawa, Satoshi; Baba, Junko; Okamoto, Masao Chemical and Pharmaceutical Bulletin, Vol. 36, Issue 1 https://doi.org/10.1248/cpb.36.22	journal	January 1988
Synthesis and Characterization of Ionene-Polyamide Materials as Candidates for New Gas Separation Membranes Bara, Jason E.; O’Harra, Kathryn E.; Durbin, Marlow M. MRS Advances, Vol. 3, Issue 52 https://doi.org/10.1557/adv.2018.376	journal	January 2018
Study of CuI catalyzed coupling reactions of aryl bromides with imidazole and aliphatic amines under microwave dielectric heating Veverková, Eva; Toma, Štefan Chemical Papers, Vol. 62, Issue 3 https://doi.org/10.2478/s11696-008-0033-z	journal	January 2008
Synthesis and Performance of Aromatic Polyamide Ionenes as Gas Separation Membranes O’Harra, Kathryn E.; Kammakakam, Irshad; Noll, Danielle M. Membranes, Vol. 10, Issue 3 https://doi.org/10.3390/membranes10030051	journal	March 2020
Designing Imidazolium Poly(amide-amide) and Poly(amide-imide) Ionenes and Their Interactions with Mono- and Tris(imidazolium) Ionic Liquids O’Harra, Kathryn E.; Noll, Danielle M.; Kammakakam, Irshad Polymers, Vol. 12, Issue 6 https://doi.org/10.3390/polym12061254	journal	May 2020

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