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Feasibility of TEMPO-functionalized imidazolium, ammonium and pyridinium salts as redox-active carriers in ethaline deep eutectic solvent for energy storage

Journal Article · · Molecular Systems Design & Engineering
DOI:https://doi.org/10.1039/d0me00038h· OSTI ID:1803807
The discovery of electrolytes that have low vapor pressures and high solubility towards redox active species with an ability to undergo multiple electron transfer reactions is a challenge to realize in large-scale energy storage. In this work, we investigate the feasibility of (2,2,6,6-tetramethylpiperidin-1-yl)oxyl (TEMPO) derived halide salts as redox active species in ethaline (1 : 2 ethylene glycol : choline chloride), a deep eutectic solvent (DES). Hydrogen bonding and electrostatic interactions achieved by the functionalization of TEMPO are shown to improve solubility in ethaline. This is the first study evaluating the physical properties and electrochemical behavior of the newly synthesized TEMPO-salts in ethaline providing insight into the impact of chemical functionality on the utility of these redox active species in DESs.
Research Organization:
Case Western Reserve Univ., Cleveland, OH (United States)
Sponsoring Organization:
USDOE Office of Science (SC), Basic Energy Sciences (BES)
Grant/Contract Number:
SC0019409
OSTI ID:
1803807
Alternate ID(s):
OSTI ID: 1635411
Journal Information:
Molecular Systems Design & Engineering, Journal Name: Molecular Systems Design & Engineering Journal Issue: 6 Vol. 5; ISSN 2058-9689
Publisher:
Royal Society of ChemistryCopyright Statement
Country of Publication:
United States
Language:
English

References (53)

A Highly Concentrated Catholyte Based on a Solvate Ionic Liquid for Rechargeable Flow Batteries journal March 2015
A Total Organic Aqueous Redox Flow Battery Employing a Low Cost and Sustainable Methyl Viologen Anolyte and 4-HO-TEMPO Catholyte journal December 2015
Redox-Flow Batteries: From Metals to Organic Redox-Active Materials journal November 2016
An Aqueous Redox-Flow Battery with High Capacity and Power: The TEMPTMA/MV System journal October 2016
Application of Hole Theory to the Viscosity of Ionic and Molecular Liquids journal August 2004
Direct, Mild, and Selective Synthesis of Unprotected Dialdo-Glycosides journal October 2006
Studying Two Series of Ternary Deep Eutectic Solvents (Choline Chloride–Urea–Glycerol) and (Choline Chloride–Malic Acid–Glycerol), Synthesis and Characterizations journal February 2017
Are deep eutectic solvents benign or toxic? journal February 2013
Electrochemical properties of a non-aqueous redox battery with all-organic redox couples journal October 2015
Organic radical battery: nitroxide polymers as a cathode-active material journal November 2004
The development of an all copper hybrid redox flow battery using deep eutectic solvents journal June 2013
Physicochemical properties of ammonium-based deep eutectic solvents and their electrochemical evaluation using organometallic reference redox systems journal December 2013
Stability of aqueous electrolytes based on LiFSI and NaFSI journal October 2019
Symmetric-cell characterization of the redox flow battery system: Application to the detection of degradations journal October 2019
Density, transport properties and electrochemical potential windows for the 2-hydroxy-N,N,N-trimethylethanaminium chlorides based ionic liquids at several temperatures journal June 2015
Measurement and PC-SAFT modeling of solid-liquid equilibrium of deep eutectic solvents of quaternary ammonium chlorides and carboxylic acids journal September 2017
Thermodynamic properties of hydrophobic deep eutectic solvents and solubility of water and HMF in them: Measurements and PC-SAFT modeling journal June 2019
Physical properties of seven deep eutectic solvents based on l-proline or betaine journal April 2019
The use of ionic liquids based on choline chloride for metal deposition: A green alternative? journal August 2009
Shifting redox potential of nitroxyl radical by introducing an imidazolium substituent and its use in aqueous flow batteries journal April 2019
Glycerol-based deep eutectic solvents: Physical properties journal March 2016
Choline chloride based deep eutectic solvents selection and liquid-liquid equilibrium for separation of dimethyl carbonate and ethanol journal February 2019
Prospects of applying ionic liquids and deep eutectic solvents for renewable energy storage by means of redox flow batteries journal February 2014
Choline-based deep eutectic solvents for CO2 separation: Review and thermodynamic analysis journal December 2018
Extraction of polyphenolic antioxidants from orange peel waste using deep eutectic solvents journal November 2018
Removing phenolic pollutants using Deep Eutectic Solvents journal November 2019
Densities of aqueous mixtures of (choline chloride+ethylene glycol) and (choline chloride+malonic acid) deep eutectic solvents in temperature range 283.15–363.15K journal January 2015
Separation Performance of BioRenewable Deep Eutectic Solvents journal March 2015
Physical Properties of the Pure Deep Eutectic Solvent, [ChCl]:[Lev] (1:2) DES, and Its Binary Mixtures with Alcohols journal October 2016
Pyridine and Pyridinium Electrochemistry on Polycrystalline Gold Electrodes and Implications for CO 2 Reduction journal May 2015
Aqueous 2,2,6,6-Tetramethylpiperidine- N -oxyl Catholytes for a High-Capacity and High Current Density Oxygen-Insensitive Hybrid-Flow Battery journal January 2017
Status and Prospects of Organic Redox Flow Batteries toward Sustainable Energy Storage journal August 2019
Deep Eutectic Solvents (DESs) and Their Applications journal October 2014
Deep Eutectic Solvents Formed between Choline Chloride and Carboxylic Acids:  Versatile Alternatives to Ionic Liquids journal July 2004
Phosphonium-Based Ionic Liquids Analogues and Their Physical Properties journal November 2010
Application of Hole Theory to Define Ionic Liquids by their Transport Properties journal May 2007
1-Oxo-2,2,6,6-tetramethylpiperidinium bromide converts α-H N,N-dialkylhydroxylamines to nitrones via a two-electron oxidation mechanism journal October 2018
Room temperature deep eutectic solvents of (1S)-(+)-10-camphorsulfonic acid and sulfobetaines: hydrogen bond-based mixtures with low ionicity and structure-dependent toxicity journal January 2015
A cathode ray polarograph. Part II.—The current-voltage curves journal January 1948
Novel solvent properties of choline chloride/urea mixturesElectronic supplementary information (ESI) available: spectroscopic data. See http://www.rsc.org/suppdata/cc/b2/b210714g/ journal November 2002
Nitroxyl radicals: electrochemical redox behaviour and structure–activity relationships journal January 2007
Deep eutectic solvents: syntheses, properties and applications journal January 2012
Analysis of Recent Measurements of the Viscosity of Glasses journal May 1992
Oscillographic polarography with periodical triangular voltage journal January 1948
Plating Utilization of Carbon Felt in a Hybrid Flow Battery journal August 2015
Communication—Iron Ionic Liquid Electrolytes for Redox Flow Battery Applications journal January 2016
Electrochemical Properties of an All-Organic Redox Flow Battery Using 2,2,6,6-Tetramethyl-1-Piperidinyloxy and N-Methylphthalimide journal January 2011
Performance of a Non-Aqueous Vanadium Acetylacetonate Prototype Redox Flow Battery: Examination of Separators and Capacity Decay journal December 2014
Avoiding Pitfalls in the Determination of Reliable Electrochemical Kinetics Parameters for the Cu 2+ → Cu 1+ Reduction Reaction in Deep Eutectic Solvents journal January 2018
Effect of Solvent Polarity on the One-electron Oxidation of Cyclic Nitroxyl Radicals journal July 2007
Pyrrolidinium salt based binary and ternary deep eutectic solvents: green preparations and physiochemical property characterizations journal July 2018
The physicochemical and thermodynamic properties of the choline chloride-based deep eutectic solvents journal January 2017
Using Deep Eutectic Solvents for the Removal of Glycerol from Palm Oil-Based Biodiesel journal December 2010

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