Electrochemical Evaluation of a Napthalene Diimide Derivative for Potential Application in Aqueous Organic Redox Flow Batteries

Wiberg, Cedrik; Owusu, Francis; Wang, Ergang; Ahlberg, Elisabet

doi:10.1002/ente.201900843

Cited by 27 publications

(24 citation statements)

References 53 publications

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“…87 A quaternary amine-functionalized NDI was synthesized by Wiberg et al, which shows a solubility of 0.68 M in water, and the redox potential is −0.13 V (vs SHE) in 1 M H 2 SO 4 . 71 This NDI derivative shows excellent charge− discharge stability, and no degradation is detected after a cycling test for 1 week. N-Hydroxyphthalimide (NHPI) was recently reported by Tian et al to exhibit excellent electrochemical reversibility with a high redox potential (+1.3 V vs SHE) in 1 M H 2 SO 4 aqueous electrolyte solution using acetonitrile (ACN) as a cosolvent.…”

Section: Redox-active Organic Electrolytesmentioning

confidence: 91%

“…The first studies of organic electrolyte materials have been performed with a system pairing a highly soluble dihydroxybenzene derivative, tiron, with Pb/PbSO 4 in strong acidic electrolytes. , From that time there has emerged many conjugated compounds/polymers as organic electrolytes for aqueous flow batteries (Figure and Table ). In an acidic aqueous system the organic anolyte materials include the derivatives/polymers of quinone, phenazine, imide, and so on, ,,,,,− while the organic catholyte materials cover many derivatives/polymers of quinone, thiazine dye, imide, and so on. − ,,,,, …”

Section: Redox-active Organic Electrolytesmentioning

confidence: 99%

“…Typical redox-active organic molecules for acidic aqueous system and their solubility, number of electrons transferred, and theoretical capacity. 9,10-Anthraquinone-2,7-disulfonic acid (2,7-AQDS), 4,5-dihydroxy-1,3-benzenedisulfonic acid (BQDSH 2 , tiron), , anthraquinone-2-sulfonic acid (AQS), 3,4-dihydroxy-9,10-anthraquinone-2-sulfonic acid (ARS), quinizarin-SO 3 -TKMP, alizarin S. Red-TKMP, 3,6-dihydroxy-2,4-dimethylbenzenesulfonic acid (DHDMBS), 1,8-dihydroxyanthraquinone-2,7-disulfonic acid (DHAQDS), 1,4-dihydroxyanthraquinone-2,3-dimethylsulfonic acid (DHAQDMS), 4,4′-biphenol-3,3′,5,5′-tetrasulfonic acid (4,4′-BPTS), lignosulfonate, polyhydroquinone (PHQ), 2,3,5,6-tetrakis((dimethylamino)methyl)hydroquinone (FQH 2 ), 2,3-diaza-9,10-anthracenedione (DAD), 2,3-diaza-6-methoxy-anthracene-9,10-dione (DAD(MeO)), 2,3-diaza-5,8-dihydroxy-anthracene-9,10-dione (DADdi(OH)), 5,8-dihydroxy-2,3-phthalazine (DHP), 5,8-dihydroxy-6-methoxy-2,3-phthalazine (DHP(MeO), 5,8-dihydroxy-6,7-dimethyl-2,3-phthalazine (DHP(Me) 2 , dopamine (DP), 3,3′,5,5′-tetramethylaminemethylene-4,4′-biphenol (TABP), 2-methoxy-1,4-hydroquinone (MHQ), 2-((2,5-dihydroxyphenyl)sulfanyl)ethan-1-aminium chloride (SEAHQ), methylene blue (MB), , Neutral Red (NR) or desalted Basic Red 5 (d-BR5), Azure A, promethazine (PMZ), chlorpromazine (CPZ), quaternary amine-functionalized naphthalenediimide (NDI), naphthalene-1,4,5,8-tetracarboxylic acid dianhydride–ethylenediamine copolymer (PI1), naphthalene-1,4,5,8-tetracarboxylic acid dianhydride- p -phenylenediamine copolymer (PI2), N -hydroxyphthalimide (NHPI), and 5,5′-indigodisulfonic acid (IC-H) …”

Section: Redox-active Organic Electrolytesmentioning

confidence: 99%

“…The electrochemical properties of NDIs can be tuned by introducing suitable electron-donating or electron-withdrawing groups into the naphthalene core while the addition of hydrophilic groups to the imide nitrogen facilitates the improvement of water-solubility . A quaternary amine-functionalized NDI was synthesized by Wiberg et al, which shows a solubility of 0.68 M in water, and the redox potential is −0.13 V (vs SHE) in 1 M H 2 SO 4 . This NDI derivative shows excellent charge–discharge stability, and no degradation is detected after a cycling test for 1 week.…”

Section: Redox-active Organic Electrolytesmentioning

confidence: 99%

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Organic Flow Batteries: Recent Progress and Perspectives

Cao

Tian

et al. 2020

Energy Fuels

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As a necessary supplement to clean renewable energy, aqueous flow batteries have become one of the most promising next-generation energy storage and conversion devices because of their excellent safety, high efficiency, flexibility, low cost, and particular capability of being scaled severally in light of energy and power density. The water-soluble redox-active electrolytes are the core components of aqueous flow batteries. The redox-active organic molecules have leaped to the more important electrolytes than conventional inorganic species because of their structural diversity, tailorability, and potential low cost. Much research work was conducted on organic electrolytes for designing high-performance aqueous flow batteries. The motivation of this review is to summarize and present the structure features, property evaluation methods, performance improvement schemes and battery design principles. The detailed functionalization methods to improve the physical and chemical performances of organic electrolytes including redox potential, reaction kinetic rate, solubility, and permeability have been emphatically provided and analyzed. Meanwhile, the further development prospect of aqueous organic electrolytes was put forward.

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Section: Redox-active Organic Electrolytesmentioning

confidence: 91%

Section: Redox-active Organic Electrolytesmentioning

confidence: 99%

Section: Redox-active Organic Electrolytesmentioning

confidence: 99%

Section: Redox-active Organic Electrolytesmentioning

confidence: 99%

See 2 more Smart Citations

Organic Flow Batteries: Recent Progress and Perspectives

Cao

Tian

et al. 2020

Energy Fuels

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“…The coordination reaction can also be used to reversibly store the hydronium (H 3 O + ), indicating the possibility of developing the organic hydronium batteries . Furthermore, the soluble organic molecules can be used as active materials for flow batteries . Organic molecules with a much larger size than metal ions can be efficiently separated by a size‐exclusion membrane, which can be used to reduce costs .…”

Section: Introductionmentioning

confidence: 99%

Progress of Organic Electrodes in Aqueous Electrolyte for Energy Storage and Conversion

et al. 2020

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She received her Ph.D. from Fudan University in 2017 supervised by Prof. Yongyao Xia. Her research mainly focuses on novel electrolytes and electrode materials for lowtemperature applications, including lithiumion batteries, sodium-ion batteries, electrochemical capacitors, and new devices. Zhaowei Guo received her B.Sc. degree in chemistry from Fudan University (2015). She then joined the Department of Chemistry of Fudan University as aP h.D. student under the supervision of Prof. Yonggang Wang. Her research focuses on organic electrode development and the novel applications of aqueous rechargeable batteries. Yonggang Wang received his Ph.D. in physical chemistry from Fudan University in 2007. From 2007 to 2011, he worked as ap ostdoctoral research associate at AIST, Japan. He is currently af ull Professor in the Department of Chemistry at Fudan University.H is research interests include electrochemical functional materials and their application in lithium-ion batteries, metalair batteries, supercapacitors, and fuel cells.

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Controlling π–π Interactions of Highly Soluble Naphthalene Diimide Derivatives for Neutral pH Aqueous Redox Flow Batteries

et al. 2023

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limited fundamentally, and more tunable charge carriers must be found. Organic molecules are compelling candidates, [5][6][7] because there is an inexhaustible supply of carbon, hydrogen, nitrogen, and oxygen on earth. In principle, their properties can be varied over a great range by changing the molecular architecture and employing functional groups. The ideal charge carrier should display fully reversible redox reactions without degradation, be highly soluble in water, and operate at neutral pH.Robust redox-activity can be achieved using aromatic systems that delocalize the charge across the whole molecule for extra stability. But the non-polar nature of aromatics can lower the solubility in water. Another serious challenge is that the radical intermediates may be highly reactive leading to undesirable side reactions and fading of the battery performance. The pH of the electrolyte solutions during battery operation deserves special attention. Because many organic systems employ proton-coupled electron transfer to achieve charge neutrality, [7][8][9][10][11][12] highly acidic or basic conditions are often encountered. However, an excess of H + ions can corrode cell components and trigger undesirable reactions. [13] In addition, highly concentrated OHin the alkaline solution diminishes volumetric energy density. [13,14] Naphthalene diimide (NDI) is an ideal platform for systematically implementing advantageous design principles, because it Organic redox-active molecules are a promising platform for designing sustainable, cheap, and safe charge carriers for redox flow batteries. However, radical formation during the electron-transfer process causes severe side reactions and reduces cyclability. This problem is mitigated by using naphthalene diimide (NDI) molecules and regulating their π-π interactions. The longrange π-stacking of NDI molecules, which leads to precipitation, is disrupted by tethering four ammonium functionalities, and the solubility approaches 1.5 m in water. The gentle π-π interactions induce clustering and disassembling of the NDI molecules during the two-electron transfer processes. When the radical anion forms, the antiferromagnetic coupling develops tetramer and dimer and nullifies the radical character. In addition, short-range-order NDI clusters at 1 m concentration are not precipitated but inhibit crossover. They are disassembled in the subsequent electron-transfer process, and the negatively charged NDI core strongly interacts with ammonium groups. These behaviors afford excellent RFB performance, demonstrating 98% capacity retention for 500 cycles at 25 mA cm -2 and 99.5% Coulombic efficiency with 2 m electron storage capacity.

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Electrochemical Evaluation of a Napthalene Diimide Derivative for Potential Application in Aqueous Organic Redox Flow Batteries

Cited by 27 publications

References 53 publications

Organic Flow Batteries: Recent Progress and Perspectives

Organic Flow Batteries: Recent Progress and Perspectives

Progress of Organic Electrodes in Aqueous Electrolyte for Energy Storage and Conversion

Controlling π–π Interactions of Highly Soluble Naphthalene Diimide Derivatives for Neutral pH Aqueous Redox Flow Batteries

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