Proton Transport in Imidazoles: Unraveling the Role of Supramolecular Structure

Cosby, James T.; Holt, Adam P.; Griffin, Phillip; Wang, Yangyang; Sangoro, Joshua R.

doi:10.1021/acs.jpclett.5b01887

Title: Proton Transport in Imidazoles: Unraveling the Role of Supramolecular Structure

Abstract

The impact of supramolecular hydrogen bonded networks on dynamics and charge transport in 2-ethyl-4-methylimidazole (2E4MIm), a model proton-conducting system, is investigated by broadband dielectric spectroscopy, depolarized dynamic light scattering, viscometry, and calorimetry. It is observed that the slow, Debye-like relaxation reflecting the supramolecular structure in neat 2E4MIm is eliminated upon the addition of minute amounts of levulinic acid. This is attributed to the dissociation of imidazole molecules and the breaking down of hydrogen-bonded chains, which leads to a 10-fold enhancement of ionic conductivity.

Authors:

Cosby, James T. ^[1]; Holt, Adam P. ^[1]; Griffin, Phillip ^[2]; Wang, Yangyang ^[3]; Sangoro, Joshua R. ^[1]

Univ. of Tennessee, Knoxville, TN (United States)
Univ. of Pennsylvania, Philadelphia, PA (United States)
Oak Ridge National Lab. (ORNL), Oak Ridge, TN (United States)

Publication Date:: Fri Sep 18 00:00:00 EDT 2015

Research Org.:: Oak Ridge National Laboratory (ORNL). Center for Nanophase Materials Sciences (CNMS)

Sponsoring Org.:: USDOE Office of Science (SC)

OSTI Identifier:: 1222571

Grant/Contract Number:: AC05-00OR22725

Resource Type:: Accepted Manuscript

Journal Name:: Journal of Physical Chemistry Letters

Additional Journal Information:: Journal Volume: 6; Journal Issue: 19; Journal ID: ISSN 1948-7185

Publisher:: American Chemical Society

Country of Publication:: United States

Language:: English

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

Citation Formats


                    Cosby, James T., Holt, Adam P., Griffin, Phillip, Wang, Yangyang, and Sangoro, Joshua R. Proton Transport in Imidazoles: Unraveling the Role of Supramolecular Structure.  United States: N. p., 2015. 
Web.  doi:10.1021/acs.jpclett.5b01887.

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                    Cosby, James T., Holt, Adam P., Griffin, Phillip, Wang, Yangyang, & Sangoro, Joshua R. Proton Transport in Imidazoles: Unraveling the Role of Supramolecular Structure.  United States.  https://doi.org/10.1021/acs.jpclett.5b01887

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                    Cosby, James T., Holt, Adam P., Griffin, Phillip, Wang, Yangyang, and Sangoro, Joshua R. Fri .  
"Proton Transport in Imidazoles: Unraveling the Role of Supramolecular Structure".  United States.  https://doi.org/10.1021/acs.jpclett.5b01887.  https://www.osti.gov/servlets/purl/1222571.

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@article{osti_1222571,

  title        = {Proton Transport in Imidazoles: Unraveling the Role of Supramolecular Structure},

  author       = {Cosby, James T. and Holt, Adam P. and Griffin, Phillip and Wang, Yangyang and Sangoro, Joshua R.},

  abstractNote = {The impact of supramolecular hydrogen bonded networks on dynamics and charge transport in 2-ethyl-4-methylimidazole (2E4MIm), a model proton-conducting system, is investigated by broadband dielectric spectroscopy, depolarized dynamic light scattering, viscometry, and calorimetry. It is observed that the slow, Debye-like relaxation reflecting the supramolecular structure in neat 2E4MIm is eliminated upon the addition of minute amounts of levulinic acid. This is attributed to the dissociation of imidazole molecules and the breaking down of hydrogen-bonded chains, which leads to a 10-fold enhancement of ionic conductivity.},

  doi          = {10.1021/acs.jpclett.5b01887},

  journal      = {Journal of Physical Chemistry Letters},

  number       = 19,

  volume       = 6,

  place        = {United States},

  year         = {Fri Sep 18 00:00:00 EDT 2015},

  month        = {Fri Sep 18 00:00:00 EDT 2015}

}

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https://doi.org/10.1021/acs.jpclett.5b01887

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Works referencing / citing this record:

Conformational aspects of polymorphs and phases of 2-propyl-1 H -benzimidazole
journal, September 2018

Zuñiga, Fco. Javier; Cruz-Cabeza, Aurora J.; Aretxabaleta, Xabier M.
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Conformational aspects of polymorphs and phases of 2-propyl-1 H -benzimidazole
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Zuñiga, Fco. Javier; Cruz-Cabeza, Aurora J.; Aretxabaleta, Xabier M.
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Title: Proton Transport in Imidazoles: Unraveling the Role of Supramolecular Structure

Abstract

Citation Formats

Structure and dynamics of monohydroxy alcohols—Milestones towards their microscopic understanding, 100 years after Debye journal, December 2014

On the relaxation between Debye and nonexponential relaxation in supercooled monohydric alcohols and water: A solution study journal, August 1989

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Experimental studies of Debye-like process and structural relaxation in mixtures of 2-ethyl-1-hexanol and 2-ethyl-1-hexyl bromide journal, October 2012

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Nuclear-Magnetic-Resonance Measurements Reveal the Origin of the Debye Process in Monohydroxy Alcohols journal, December 2010

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Dielectric Relaxation and Rheological Behavior of Supramolecular Polymeric Liquid journal, April 2013

Interactions of histidine and other imidazole derivatives with transition metal ions in chemical and biological systems journal, August 1974

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Transport in Proton Conductors for Fuel-Cell Applications: Simulations, Elementary Reactions, and Phenomenology journal, October 2004

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Charge transport in poly-imidazole membranes: a fresh appraisal of the Grotthuss mechanism journal, January 2012

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Protonic Conductivity in Imidazole Single Crystal journal, March 1970

The diffusion mechanism of an excess proton in imidazole molecule chains: first results of an ab initio molecular dynamics study journal, December 2001

Hydrogen bonding at the water surface revealed by isotopic dilution spectroscopy journal, June 2011

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Low-Melting, Low-Viscous, Hydrophobic Ionic Liquids: Aliphatic Quaternary Ammonium Salts with Perfluoroalkyltrifluoroborates journal, January 2005

The random free‐energy barrier model for ac conduction in disordered solids journal, September 1988

Universality of ac conduction in disordered solids journal, July 2000

Charge Transport and Glassy Dynamics in Ionic Liquids journal, November 2011

Charge Transport and Structural Dynamics in Carboxylic-Acid-Based Deep Eutectic Mixtures journal, July 2014

Analysis of the Dielectric Permittivity of Suspensions by Means of the Logarithmic Derivative of Its Real Part journal, May 2002

Conformational aspects of polymorphs and phases of 2-propyl-1 H -benzimidazole journal, September 2018

Conformational aspects of polymorphs and phases of 2-propyl-1 H -benzimidazole text, January 2018

Structure and dynamics of monohydroxy alcohols—Milestones towards their microscopic understanding, 100 years after Debye
journal, December 2014

On the relaxation between Debye and nonexponential relaxation in supercooled monohydric alcohols and water: A solution study
journal, August 1989

Rotation of Imidazole in the Solid State and its Significance in deciding the Nature of Charge Migration in Biological Materials
journal, May 1968

Shear-Modulus Investigations of Monohydroxy Alcohols: Evidence for a Short-Chain-Polymer Rheological Response
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Experimental studies of Debye-like process and structural relaxation in mixtures of 2-ethyl-1-hexanol and 2-ethyl-1-hexyl bromide
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Watching Hydrogen-Bonded Structures in an Alcohol Convert from Rings to Chains
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Observation of the slow, Debye-like relaxation in hydrogen-bonded liquids by dynamic light scattering
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Dielectric Relaxation and Rheological Behavior of Supramolecular Polymeric Liquid
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Interactions of histidine and other imidazole derivatives with transition metal ions in chemical and biological systems
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Biological wires, communication systems, and implications for disease
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A Supramolecular Ferroelectric Realized by Collective Proton Transfer
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Enhancement of Proton Conduction at Low Humidity by Incorporating Imidazole Microcapsules into Polymer Electrolyte Membranes
journal, June 2012

One-dimensional imidazole aggregate in aluminium porous coordination polymers with high proton conductivity
journal, September 2009

Protic ionic liquids: Fuel cell applications
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journal, January 2012

First principles molecular dynamics study of proton dynamics and transport in phosphoric acid/imidazole (2:1) system
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Protonic Conductivity in Imidazole Single Crystal
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Hydrogen bonding at the water surface revealed by isotopic dilution spectroscopy
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Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications
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Low-Melting, Low-Viscous, Hydrophobic Ionic Liquids: Aliphatic Quaternary Ammonium Salts with Perfluoroalkyltrifluoroborates
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journal, September 1988

Universality of ac conduction in disordered solids
journal, July 2000

Charge Transport and Glassy Dynamics in Ionic Liquids
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Charge Transport and Structural Dynamics in Carboxylic-Acid-Based Deep Eutectic Mixtures
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Analysis of the Dielectric Permittivity of Suspensions by Means of the Logarithmic Derivative of Its Real Part
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