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

Journal Article · Fri Sep 18 00:00:00 EDT 2015 · Journal of Physical Chemistry Letters

DOI:https://doi.org/10.1021/acs.jpclett.5b01887· OSTI ID:1222571

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)

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.

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

Sponsoring Organization:: USDOE Office of Science (SC)

Grant/Contract Number:: AC05-00OR22725

OSTI ID:: 1222571

Journal Information:: Journal of Physical Chemistry Letters, Vol. 6, Issue 19; ISSN 1948-7185

Publisher:: American Chemical SocietyCopyright Statement

Country of Publication:: United States

Language:: English

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Cited by: 21 works

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References (35)

Structure and dynamics of monohydroxy alcohols—Milestones towards their microscopic understanding, 100 years after Debye Böhmer, Roland; Gainaru, Catalin; Richert, Ranko Physics Reports, Vol. 545, Issue 4 https://doi.org/10.1016/j.physrep.2014.07.005	journal	December 2014
On the relaxation between Debye and nonexponential relaxation in supercooled monohydric alcohols and water: A solution study Floriano, M. A.; Angell, C. A. The Journal of Chemical Physics, Vol. 91, Issue 4 https://doi.org/10.1063/1.457013	journal	August 1989
Rotation of Imidazole in the Solid State and its Significance in deciding the Nature of Charge Migration in Biological Materials Daycock, J. T.; Jones, G. P.; Evans, J. R. N. Nature, Vol. 218, Issue 5142 https://doi.org/10.1038/218672a0	journal	May 1968
Shear-Modulus Investigations of Monohydroxy Alcohols: Evidence for a Short-Chain-Polymer Rheological Response Gainaru, C.; Figuli, R.; Hecksher, T. Physical Review Letters, Vol. 112, Issue 9 https://doi.org/10.1103/PhysRevLett.112.098301	journal	March 2014
Experimental studies of Debye-like process and structural relaxation in mixtures of 2-ethyl-1-hexanol and 2-ethyl-1-hexyl bromide Preuß, M.; Gainaru, C.; Hecksher, T. The Journal of Chemical Physics, Vol. 137, Issue 14 https://doi.org/10.1063/1.4755754	journal	October 2012
Watching Hydrogen-Bonded Structures in an Alcohol Convert from Rings to Chains Singh, Lokendra P.; Richert, Ranko Physical Review Letters, Vol. 109, Issue 16 https://doi.org/10.1103/PhysRevLett.109.167802	journal	October 2012
Nuclear-Magnetic-Resonance Measurements Reveal the Origin of the Debye Process in Monohydroxy Alcohols Gainaru, C.; Meier, R.; Schildmann, S. Physical Review Letters, Vol. 105, Issue 25 https://doi.org/10.1103/PhysRevLett.105.258303	journal	December 2010
Observation of the slow, Debye-like relaxation in hydrogen-bonded liquids by dynamic light scattering Wang, Yangyang; Griffin, Philip J.; Holt, Adam The Journal of Chemical Physics, Vol. 140, Issue 10 https://doi.org/10.1063/1.4867913	journal	March 2014
Dielectric Relaxation and Rheological Behavior of Supramolecular Polymeric Liquid Lou, Nan; Wang, Yangyang; Li, Xiaopeng Macromolecules, Vol. 46, Issue 8 https://doi.org/10.1021/ma400088w	journal	April 2013
Interactions of histidine and other imidazole derivatives with transition metal ions in chemical and biological systems Sundberg, Richard J.; Martin, R. Bruce Chemical Reviews, Vol. 74, Issue 4 https://doi.org/10.1021/cr60290a003	journal	August 1974
Comprehensive Review in Current Developments of Imidazole-Based Medicinal Chemistry: IMIDAZOLE-BASED MEDICINAL CHEMISTRY Zhang, Ling; Peng, Xin-Mei; Damu, Guri L. V. Medicinal Research Reviews, Vol. 34, Issue 2 https://doi.org/10.1002/med.21290	journal	June 2013
Transport in Proton Conductors for Fuel-Cell Applications: Simulations, Elementary Reactions, and Phenomenology Kreuer, Klaus-Dieter; Paddison, Stephen J.; Spohr, Eckhard Chemical Reviews, Vol. 104, Issue 10 https://doi.org/10.1021/cr020715f	journal	October 2004
Proton Conduction in a MIL-53(Al) Metal–Organic Framework: Confinement versus Host/Guest Interaction Eisbein, Emanuel; Joswig, Jan-Ole; Seifert, Gotthard The Journal of Physical Chemistry C, Vol. 118, Issue 24 https://doi.org/10.1021/jp5043969	journal	June 2014
Biological wires, communication systems, and implications for disease Friesen, Douglas E.; Craddock, Travis J. A.; Kalra, Aarat P. Biosystems, Vol. 127 https://doi.org/10.1016/j.biosystems.2014.10.006	journal	January 2015
A Supramolecular Ferroelectric Realized by Collective Proton Transfer Horiuchi, Sachio; Kumai, Reiji; Tokura, Yoshinori Angewandte Chemie International Edition, Vol. 46, Issue 19 https://doi.org/10.1002/anie.200700407	journal	May 2007
Hydrogen-Bonding Molecular Chains for High-Temperature Ferroelectricity Horiuchi, Sachio; Kumai, Reiji; Tokura, Yoshinori Advanced Materials, Vol. 23, Issue 18 https://doi.org/10.1002/adma.201100359	journal	April 2011
Enhancement of Proton Conduction at Low Humidity by Incorporating Imidazole Microcapsules into Polymer Electrolyte Membranes Wang, Jingtao; Yue, Xiujun; Zhang, Zizhuo Advanced Functional Materials, Vol. 22, Issue 21 https://doi.org/10.1002/adfm.201201436	journal	June 2012
One-dimensional imidazole aggregate in aluminium porous coordination polymers with high proton conductivity Bureekaew, Sareeya; Horike, Satoshi; Higuchi, Masakazu Nature Materials, Vol. 8, Issue 10 https://doi.org/10.1038/nmat2526	journal	September 2009
Protic ionic liquids: Fuel cell applications Yasuda, Tomohiro; Watanabe, Masayoshi MRS Bulletin, Vol. 38, Issue 7 https://doi.org/10.1557/mrs.2013.153	journal	July 2013
Brønsted Acid−Base Ionic Liquids as Proton-Conducting Nonaqueous Electrolytes Noda, Akihiro; Susan, Md. Abu Bin Hasan; Kudo, Kenji The Journal of Physical Chemistry B, Vol. 107, Issue 17 https://doi.org/10.1021/jp022347p	journal	May 2003
A Computer Simulation Model for Proton Transport in Liquid Imidazole Chen, Hanning; Yan, Tianying; Voth, Gregory A. The Journal of Physical Chemistry A, Vol. 113, Issue 16 https://doi.org/10.1021/jp811156r	journal	March 2009
Charge transport in poly-imidazole membranes: a fresh appraisal of the Grotthuss mechanism Mangiatordi, Giuseppe Felice; Butera, Valeria; Russo, Nino Physical Chemistry Chemical Physics, Vol. 14, Issue 31 https://doi.org/10.1039/c2cp23727j	journal	January 2012
First principles molecular dynamics study of proton dynamics and transport in phosphoric acid/imidazole (2:1) system Vilčiauskas, Linas; Tuckerman, Mark E.; Melchior, Jan P. Solid State Ionics, Vol. 252 https://doi.org/10.1016/j.ssi.2013.07.003	journal	December 2013
Quantum Chemistry Study of Proton Transport in Imidazole Chains Kumar, Milan; Venkatnathan, Arun The Journal of Physical Chemistry B, Vol. 119, Issue 7 https://doi.org/10.1021/jp508994c	journal	February 2015
Molecular Origin of Enhanced Proton Conductivity in Anhydrous Ionic Systems Wojnarowska, Zaneta; Paluch, Krzysztof J.; Shoifet, Evgeni Journal of the American Chemical Society, Vol. 137, Issue 3 https://doi.org/10.1021/ja5103458	journal	January 2015
Protonic Conductivity in Imidazole Single Crystal Kawada, A.; McGhie, A. R.; Labes, M. M. The Journal of Chemical Physics, Vol. 52, Issue 6 https://doi.org/10.1063/1.1673447	journal	March 1970
The diffusion mechanism of an excess proton in imidazole molecule chains: first results of an ab initio molecular dynamics study Münch, W.; Kreuer, K. -D; Silvestri, W. Solid State Ionics, Vol. 145, Issue 1-4 https://doi.org/10.1016/S0167-2738(01)00941-9	journal	December 2001
Hydrogen bonding at the water surface revealed by isotopic dilution spectroscopy Stiopkin, Igor V.; Weeraman, Champika; Pieniazek, Piotr A. Nature, Vol. 474, Issue 7350 https://doi.org/10.1038/nature10173	journal	June 2011
Ether- and alcohol-functionalized task-specific ionic liquids: attractive properties and applications Tang, Shaokun; Baker, Gary A.; Zhao, Hua Chemical Society Reviews, Vol. 41, Issue 10 https://doi.org/10.1039/c2cs15362a	journal	January 2012
Low-Melting, Low-Viscous, Hydrophobic Ionic Liquids: Aliphatic Quaternary Ammonium Salts with Perfluoroalkyltrifluoroborates Zhou, Zhi-Bin; Matsumoto, Hajime; Tatsumi, Kuniaki Chemistry - A European Journal, Vol. 11, Issue 2 https://doi.org/10.1002/chem.200400817	journal	January 2005
The random free‐energy barrier model for ac conduction in disordered solids Dyre, Jeppe C. Journal of Applied Physics, Vol. 64, Issue 5 https://doi.org/10.1063/1.341681	journal	September 1988
Universality of ac conduction in disordered solids Dyre, Jeppe C.; Schrøder, Thomas B. Reviews of Modern Physics, Vol. 72, Issue 3 https://doi.org/10.1103/RevModPhys.72.873	journal	July 2000
Charge Transport and Glassy Dynamics in Ionic Liquids Sangoro, Joshua R.; Kremer, Friedrich Accounts of Chemical Research, Vol. 45, Issue 4 https://doi.org/10.1021/ar2001809	journal	November 2011
Charge Transport and Structural Dynamics in Carboxylic-Acid-Based Deep Eutectic Mixtures Griffin, Philip J.; Cosby, Tyler; Holt, Adam P. The Journal of Physical Chemistry B, Vol. 118, Issue 31 https://doi.org/10.1021/jp503105g	journal	July 2014
Analysis of the Dielectric Permittivity of Suspensions by Means of the Logarithmic Derivative of Its Real Part Jiménez, M. L.; Arroyo, F. J.; van Turnhout, J. Journal of Colloid and Interface Science, Vol. 249, Issue 2 https://doi.org/10.1006/jcis.2001.8141	journal	May 2002

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Conformational aspects of polymorphs and phases of 2-propyl-1 H -benzimidazole Zuñiga, Fco. Javier; Cruz-Cabeza, Aurora J.; Aretxabaleta, Xabier M. IUCrJ, Vol. 5, Issue 6 https://doi.org/10.1107/s2052252518011685	journal	September 2018
Conformational aspects of polymorphs and phases of 2-propyl-1 H -benzimidazole Zuñiga, Fco. Javier; Cruz-Cabeza, Aurora J.; Aretxabaleta, Xabier M. International Union of Crystallography (IUCr) https://doi.org/10.1107/s2052252518011685/lq5016iiltsup5.hkl	text	January 2018

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