Imidazolium Cations with Exceptional Alkaline Stability: A Systematic Study of Structure–Stability Relationships

Hugar, Kristina M.; Kostalik, IV, Henry A.; Coates, Geoffrey W.

doi:10.1021/jacs.5b02879

Title: Imidazolium Cations with Exceptional Alkaline Stability: A Systematic Study of Structure–Stability Relationships

Abstract

Highly base-stable cationic moieties are a critical component of anion exchange membranes (AEMs) in alkaline fuel cells (AFCs); however, the commonly employed organic cations have limited alkaline stability. To address this problem, we synthesized and characterized the stability of a series of imidazolium cations in 1, 2, or 5 M KOH/CD₃OH at 80 °C, systematically evaluating the impact of substitution on chemical stability. The substituent identity at each position of the imidazolium ring has a dramatic effect on the overall cation stability. In conclusion, we report imidazolium cations that have the highest alkaline stabilities reported to date, >99% cation remaining after 30 days in 5 M KOH/CD₃OH at 80 °C.

Authors:

Hugar, Kristina M. ^[1]; Kostalik, IV, Henry A. ^[1]; Coates, Geoffrey W. ^[1]

Department of Chemistry and Chemical Biology, Baker Laboratory, Cornell University, Ithaca, New York 14853-1301, United States

Publication Date:: Wed Jul 01 00:00:00 EDT 2015

Research Org.:: Energy Frontier Research Centers (EFRC), Washington, D.C. (United States). Energy Materials Center at Cornell (EMC2)

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

OSTI Identifier:: 1234555

Alternate Identifier(s):: OSTI ID: 1370427

Grant/Contract Number:: SC0001086

Resource Type:: Published Article

Journal Name:: Journal of the American Chemical Society

Additional Journal Information:: Journal Name: Journal of the American Chemical Society Journal Volume: 137 Journal Issue: 27; Journal ID: ISSN 0002-7863

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

Subject:: 37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY

Citation Formats


                    Hugar, Kristina M., Kostalik, IV, Henry A., and Coates, Geoffrey W. Imidazolium Cations with Exceptional Alkaline Stability: A Systematic Study of Structure–Stability Relationships.  United States: N. p., 2015. 
Web.  doi:10.1021/jacs.5b02879.

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                    Hugar, Kristina M., Kostalik, IV, Henry A., & Coates, Geoffrey W. Imidazolium Cations with Exceptional Alkaline Stability: A Systematic Study of Structure–Stability Relationships.  United States.  https://doi.org/10.1021/jacs.5b02879

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                    Hugar, Kristina M., Kostalik, IV, Henry A., and Coates, Geoffrey W. Wed .  
"Imidazolium Cations with Exceptional Alkaline Stability: A Systematic Study of Structure–Stability Relationships".  United States.  https://doi.org/10.1021/jacs.5b02879.

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@article{osti_1234555,

  title        = {Imidazolium Cations with Exceptional Alkaline Stability: A Systematic Study of Structure–Stability Relationships},

  author       = {Hugar, Kristina M. and Kostalik, IV, Henry A. and Coates, Geoffrey W.},

  abstractNote = {Highly base-stable cationic moieties are a critical component of anion exchange membranes (AEMs) in alkaline fuel cells (AFCs); however, the commonly employed organic cations have limited alkaline stability. To address this problem, we synthesized and characterized the stability of a series of imidazolium cations in 1, 2, or 5 M KOH/CD3OH at 80 °C, systematically evaluating the impact of substitution on chemical stability. The substituent identity at each position of the imidazolium ring has a dramatic effect on the overall cation stability. In conclusion, we report imidazolium cations that have the highest alkaline stabilities reported to date, >99% cation remaining after 30 days in 5 M KOH/CD3OH at 80 °C.},

  doi          = {10.1021/jacs.5b02879},

  journal      = {Journal of the American Chemical Society},

  number       = 27,

  volume       = 137,

  place        = {United States},

  year         = {Wed Jul 01 00:00:00 EDT 2015},

  month        = {Wed Jul 01 00:00:00 EDT 2015}

}

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Chart 1: Selected Cations Investigated for Use in Alkaline Anion Exchange Membranes (AAEMs)

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Highly conductive and chemically stable alkaline anion exchange membranes via ROMP of trans -cyclooctene derivatives

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Alkaline anion exchange membranes (AAEMs) are an important component of alkaline exchange membrane fuel cells (AEMFCs), which facilitate the efficient conversion of fuels to electricity using nonplatinum electrode catalysts. However, low hydroxide conductivity and poor long-term alkaline stability of AAEMs are the major limitations for the widespread application of AEMFCs. In this paper, we report the synthesis of highly conductive and chemically stable AAEMs from the living polymerization of trans -cyclooctenes. A trans -cyclooctene–fused imidazolium monomer was designed and synthesized on gram scale. Using these highly ring-strained monomers, we produced a range of block and random copolymers. Surprisingly, AAEMs mademore »« less
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The durability of anion-exchange membranes (AEMs) in alkaline fuel cells is largely determined by the stability of anion-exchange groups. Despite continuous research efforts, the commonly employed cations still have limited stability against hydroxide that can act as a strong base and nucleophile. This work is concerned with base-catalyzed degradation of organic cations initiated by proton abstraction to form reactive ylides or carbenes. We report on the performance of 24 methods combining density functional theory and electronic structure methods with implicit solvation calculations for predicting pKa values of organic cations in water and DMSO. The most accurate computational protocols are obtainedmore »« less
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Title: Imidazolium Cations with Exceptional Alkaline Stability: A Systematic Study of Structure–Stability Relationships

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Guanidinium-Functionalized Anion Exchange Polymer Electrolytes via Activated Fluorophenyl-Amine Reaction journal, September 2011

Effect of ammonium groups on the properties and alkaline stability of poly(arylene ether)-based anion exchange membranes journal, November 2013

Degradation of anion exchange membranes used for hydrogen production by ultrapure water electrolysis journal, January 2014

Fast CO 2 Sequestration, Activation, and Catalytic Transformation Using N -Heterocyclic Olefins journal, July 2013

Development of phosphonium-based bicarbonate anion exchange polymer membranes journal, September 2013

A morpholinium-functionalized poly(ether sulfone) as a novel anion exchange membrane for alkaline fuel cell journal, August 2013

Quaternary Phosphonium-Based Polymers as Hydroxide Exchange Membranes journal, April 2010

Transport Properties of Hydroxide and Proton Conducting Membranes journal, April 2008

Determination of the Structure of a Novel Anion Exchange Fuel Cell Membrane by Solid-State Nuclear Magnetic Resonance Spectroscopy journal, March 2009

From curiosity to “power to change the world®” journal, December 2002

Improving the Alkaline Stability of Imidazolium Cations by Substitution journal, July 2014

Synthesis and Properties of Anion Conductive Ionomers Containing Tetraphenyl Methane Moieties journal, June 2012

Anion-exchange membranes containing diamines: preparation and stability in alkaline solution journal, November 2004

Tunable High Performance Cross-Linked Alkaline Anion Exchange Membranes for Fuel Cell Applications journal, March 2010

Synthesis and characterization of urea-containing imidazolium iodide electrolyte for dye-sensitized solar cells journal, July 2012

Imidazolium-functionalized poly(arylene ether sulfone) block copolymer as an anion exchange membrane for alkaline fuel cell journal, January 2013

Hydroxide Degradation Pathways for Substituted Trimethylammonium Cations: A DFT Study journal, April 2012

Relationships between Structure and Alkaline Stability of Imidazolium Cations for Fuel Cell Membrane Applications journal, January 2014

Decomposition pathways of an alkaline fuel cell membrane material component via evolved gas analysis journal, July 2008

Bis-imidazolium-based anion-exchange membranes for alkaline fuel cells journal, November 2012

Anion conducting poly(dialkyl benzimidazolium) salts journal, January 2011

Anion exchange membranes: Current status and moving forward journal, October 2013

Anion exchange membranes for alkaline fuel cells: A review journal, July 2011

Alkaline imidazolium- and quaternary ammonium-functionalized anion exchange membranes for alkaline fuel cell applications journal, January 2012

Preparation of alkaline anion exchange membranes based on functional poly(ether-imide) polymers for potential fuel cell applications journal, January 2009

Anion Conductive Block Poly(arylene ether)s: Synthesis, Properties, and Application in Alkaline Fuel Cells journal, July 2011

Degradation of Imidazolium- and Quaternary Ammonium-Functionalized Poly(fluorenyl ether ketone sulfone) Anion Exchange Membranes journal, November 2012

Stabilizing the Imidazolium Cation in Hydroxide-Exchange Membranes for Fuel Cells journal, August 2013

Anion Exchange Membranes by Bromination of Benzylmethyl-Containing Poly(sulfone)s journal, March 2010

Anion conductive aromatic membrane of poly(tetra phenyl ether sulfone) containing hexa-imidazolium hydroxides for alkaline fuel cell application journal, September 2014

Towards High Conductivity in Anion-Exchange Membranes for Alkaline Fuel Cells journal, June 2013

High performance porous polybenzimidazole membrane for alkaline fuel cells journal, October 2014

Alkaline stable imidazolium-based ionomers containing poly(arylene ether sulfone) side chains for alkaline anion exchange membranes journal, January 2014

Hydrogen futures: toward a sustainable energy system journal, March 2002

Steady-State dc and Impedance Investigations of H 2 /O 2 Alkaline Membrane Fuel Cells with Commercial Pt/C, Ag/C, and Au/C Cathodes journal, October 2006

Hydroxide-Stable Ionenes journal, April 2014

Hydroxyalkyl-Containing Imidazolium Homopolymers: Correlation of Structure with Conductivity journal, April 2013

Novel Hydroxide-Conducting Polyelectrolyte Composed of an Poly(arylene ether sulfone) Containing Pendant Quaternary Guanidinium Groups for Alkaline Fuel Cell Applications journal, April 2010

Methylated polybenzimidazole and its application as a blend component in covalently cross-linked anion-exchange membranes for DMFC journal, September 2014

Polybenzimidazolium-Based Solid Electrolytes journal, July 2011

Aromatic polyelectrolytes via polyacylation of pre-quaternized monomers for alkaline fuel cells journal, January 2013

Alkaline Stability of Benzyl Trimethyl Ammonium Functionalized Polyaromatics: A Computational and Experimental Study journal, September 2014

Long term investigations of silver cathodes for alkaline fuel cells journal, March 2004

Synthesis of imidazole-terminated hyperbranched polymers with POSS-branching points and their pH responsive and coordination properties journal, March 2013

Cross-linked, ETFE-derived and radiation grafted membranes for anion exchange membrane fuel cell applications journal, January 2012

Quantitative 1 H NMR Analysis of Chemical Stabilities in Anion-Exchange Membranes journal, December 2012

Cleaning the Air and Improving Health with Hydrogen Fuel-Cell Vehicles
journal, June 2005

Imidazolium-functionalized polysulfone hydroxide exchange membranes for potential applications in alkaline membrane direct alcohol fuel cells
journal, March 2012

Prospects for Alkaline Anion-Exchange Membranes in Low Temperature Fuel Cells
journal, October 2004

Highly Stable N3-Substituted Imidazolium-Based Alkaline Anion Exchange Membranes: Experimental Studies and Theoretical Calculations
journal, December 2013

Synthesis and Gas Separation Performance of Triblock Copolymer Ion Gels with a Polymerized Ionic Liquid Mid-Block
journal, April 2011

Highly Stable, Anion Conductive, Comb-Shaped Copolymers for Alkaline Fuel Cells
journal, June 2013

Poly(ethylene- co -tetrafluoroethylene)-Derived Radiation-Grafted Anion-Exchange Membrane with Properties Specifically Tailored for Application in Metal-Cation-Free Alkaline Polymer Electrolyte Fuel Cells
journal, May 2007

A Ring-Opening Metathesis Polymerization Route to Alkaline Anion Exchange Membranes: Development of Hydroxide-Conducting Thin Films from an Ammonium-Functionalized Monomer
journal, September 2009

Highly Stable Alkaline Polymer Electrolyte Based on a Poly(ether ether ketone) Backbone
journal, November 2013

Resonance Stabilized Perfluorinated Ionomers for Alkaline Membrane Fuel Cells
journal, September 2013

Phosphonium cation-containing polymers: From ionic liquids to polyelectrolytes
journal, August 2014

Novel alkaline anion exchange membranes containing pendant benzimidazolium groups for alkaline fuel cells
journal, September 2013

Alkaline Stability of Quaternary Ammonium Cations for Alkaline Fuel Cell Membranes and Ionic Liquids
journal, November 2014

Novel self-crosslinked poly(aryl ether sulfone) for high alkaline stable and fuel resistant alkaline anion exchange membranes
journal, January 2011

Anion Exchange Fuel Cell Membranes Prepared from C–H Borylation and Suzuki Coupling Reactions
journal, March 2014

Cross-linked comb-shaped anion exchange membranes with high base stability
journal, January 2014

Ion-containing polymers: new energy & clean water
journal, May 2010

A facile strategy for the synthesis of guanidinium-functionalized polymer as alkaline anion exchange membrane with improved alkaline stability
journal, March 2014

Hydroxide-ion induced degradation pathway for dimethylimidazolium groups in anion exchange membranes
journal, July 2014

A stable anion exchange membrane based on imidazolium salt for alkaline fuel cell
journal, October 2014

An assessment of alkaline fuel cell technology
journal, May 2002

Thermal and ion transport properties of hydrophilic and hydrophobic polymerized styrenic imidazolium ionic liquids
journal, July 2011

A novel guanidinium grafted poly(aryl ether sulfone) for high-performance hydroxide exchange membranes
journal, September 2010

Degradation of guanidinium-functionalized anion exchange membrane during alkaline environment
journal, August 2014

Base Stable Pyrrolidinium Cations for Alkaline Anion Exchange Membrane Applications
journal, September 2014

An Initial Degradation Reaction before Ring-Opening in Imidazolium-Based Anion Exchange Membranes: A DFT Study
journal, January 2013

New anion conducting membranes based on functionalized styrene-butadiene-styrene triblock copolymer for fuel cells applications
journal, June 2011

Recent Development of Polymer Electrolyte Membranes for Fuel Cells
journal, February 2012

Extremely Base-Resistant Organic Phosphazenium Cations
journal, January 2006

Density Functional Theory Study of Degradation of Tetraalkylammonium Hydroxides
journal, June 2010

Guanidinium-Functionalized Anion Exchange Polymer Electrolytes via Activated Fluorophenyl-Amine Reaction
journal, September 2011

Effect of ammonium groups on the properties and alkaline stability of poly(arylene ether)-based anion exchange membranes
journal, November 2013

Degradation of anion exchange membranes used for hydrogen production by ultrapure water electrolysis
journal, January 2014

Fast CO ₂ Sequestration, Activation, and Catalytic Transformation Using N -Heterocyclic Olefins
journal, July 2013

Development of phosphonium-based bicarbonate anion exchange polymer membranes
journal, September 2013

A morpholinium-functionalized poly(ether sulfone) as a novel anion exchange membrane for alkaline fuel cell
journal, August 2013

Quaternary Phosphonium-Based Polymers as Hydroxide Exchange Membranes
journal, April 2010

Transport Properties of Hydroxide and Proton Conducting Membranes
journal, April 2008

Determination of the Structure of a Novel Anion Exchange Fuel Cell Membrane by Solid-State Nuclear Magnetic Resonance Spectroscopy
journal, March 2009

From curiosity to “power to change the world®”
journal, December 2002

Improving the Alkaline Stability of Imidazolium Cations by Substitution
journal, July 2014

Synthesis and Properties of Anion Conductive Ionomers Containing Tetraphenyl Methane Moieties
journal, June 2012

Anion-exchange membranes containing diamines: preparation and stability in alkaline solution
journal, November 2004

Tunable High Performance Cross-Linked Alkaline Anion Exchange Membranes for Fuel Cell Applications
journal, March 2010

Synthesis and characterization of urea-containing imidazolium iodide electrolyte for dye-sensitized solar cells
journal, July 2012

Imidazolium-functionalized poly(arylene ether sulfone) block copolymer as an anion exchange membrane for alkaline fuel cell
journal, January 2013

Hydroxide Degradation Pathways for Substituted Trimethylammonium Cations: A DFT Study
journal, April 2012

Relationships between Structure and Alkaline Stability of Imidazolium Cations for Fuel Cell Membrane Applications
journal, January 2014

Decomposition pathways of an alkaline fuel cell membrane material component via evolved gas analysis
journal, July 2008

Bis-imidazolium-based anion-exchange membranes for alkaline fuel cells
journal, November 2012

Anion conducting poly(dialkyl benzimidazolium) salts
journal, January 2011

Anion exchange membranes: Current status and moving forward
journal, October 2013

Anion exchange membranes for alkaline fuel cells: A review
journal, July 2011

Alkaline imidazolium- and quaternary ammonium-functionalized anion exchange membranes for alkaline fuel cell applications
journal, January 2012

Preparation of alkaline anion exchange membranes based on functional poly(ether-imide) polymers for potential fuel cell applications
journal, January 2009

Anion Conductive Block Poly(arylene ether)s: Synthesis, Properties, and Application in Alkaline Fuel Cells
journal, July 2011

Degradation of Imidazolium- and Quaternary Ammonium-Functionalized Poly(fluorenyl ether ketone sulfone) Anion Exchange Membranes
journal, November 2012

Stabilizing the Imidazolium Cation in Hydroxide-Exchange Membranes for Fuel Cells
journal, August 2013

Anion Exchange Membranes by Bromination of Benzylmethyl-Containing Poly(sulfone)s
journal, March 2010

Anion conductive aromatic membrane of poly(tetra phenyl ether sulfone) containing hexa-imidazolium hydroxides for alkaline fuel cell application
journal, September 2014

Towards High Conductivity in Anion-Exchange Membranes for Alkaline Fuel Cells
journal, June 2013

High performance porous polybenzimidazole membrane for alkaline fuel cells
journal, October 2014

Alkaline stable imidazolium-based ionomers containing poly(arylene ether sulfone) side chains for alkaline anion exchange membranes
journal, January 2014

Hydrogen futures: toward a sustainable energy system
journal, March 2002

Steady-State dc and Impedance Investigations of H ₂ /O ₂ Alkaline Membrane Fuel Cells with Commercial Pt/C, Ag/C, and Au/C Cathodes
journal, October 2006

Hydroxide-Stable Ionenes
journal, April 2014

Hydroxyalkyl-Containing Imidazolium Homopolymers: Correlation of Structure with Conductivity
journal, April 2013

Novel Hydroxide-Conducting Polyelectrolyte Composed of an Poly(arylene ether sulfone) Containing Pendant Quaternary Guanidinium Groups for Alkaline Fuel Cell Applications
journal, April 2010

Methylated polybenzimidazole and its application as a blend component in covalently cross-linked anion-exchange membranes for DMFC
journal, September 2014

Polybenzimidazolium-Based Solid Electrolytes
journal, July 2011

Aromatic polyelectrolytes via polyacylation of pre-quaternized monomers for alkaline fuel cells
journal, January 2013

Alkaline Stability of Benzyl Trimethyl Ammonium Functionalized Polyaromatics: A Computational and Experimental Study
journal, September 2014

Long term investigations of silver cathodes for alkaline fuel cells
journal, March 2004

Synthesis of imidazole-terminated hyperbranched polymers with POSS-branching points and their pH responsive and coordination properties
journal, March 2013

Cross-linked, ETFE-derived and radiation grafted membranes for anion exchange membrane fuel cell applications
journal, January 2012

Quantitative ¹ H NMR Analysis of Chemical Stabilities in Anion-Exchange Membranes
journal, December 2012

Imidazolium functionalized polysulfone anion exchange membrane for fuel cell application
journal, January 2011

Hydroxide based decomposition pathways of alkyltrimethylammonium cations
journal, May 2012

Development of imidazolium-type alkaline anion exchange membranes for fuel cell application
journal, October 2012

Ion Motion in Anion and Proton-Conducting Triblock Copolymers
journal, January 2013