Solvent effect on the redox potential of quinone-semiquinone systems

Jaworski, Jan S.; Leniewska, Ewa; Kalinowski, Marek K.

doi:10.1016/s0022-0728(79)80126-6

Cited by 56 publications

(39 citation statements)

References 16 publications

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“…[51][52][53] The two-step redox behavior of Na 2 DBQ in EC:PC (1:1 v/v) and ILelectrolytes are shown in Figure 3a. In SIB applications, the dianion interacts with 2 Na + ions and releases them upon complete oxidation, which results in reversible sodiation.…”

Section: Resultsmentioning

confidence: 99%

Enhanced Cycle Performance of Quinone-Based Anodes for Sodium Ion Batteries by Attachment to Ordered Mesoporous Carbon and Use of Ionic Liquid Electrolyte

Gurkan

Qiang

Chen

et al. 2017

J. Electrochem. Soc.

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Sodium ion batteries (SIBs) have emerged as a potential alternative to lithium ion batteries due to their chemical similarities. Key considerations for SIBs include energy storage capacity, lifetime, cost, and safety. Major challenges associated with high performance organic electrodes for rechargeable batteries are their poor electrical conductivity and dissolution of the active material in common electrolytes. The poor conductivity limits the rate performance, while dissolution leads to poor cycle performance and short lifetimes. Here we demonstrate a route to address these challenges in a sodium ion battery for 2,5-disodium-1,4-benzoquinone, Na 2 DBQ (organic active material), through immobilization of the Na 2 DBQ on high surface area ordered mesoporous carbon, OMC, and use of 1-methyl-3-propylpyrrolidinium bis(fluoromethylsulfonyl)imide ionic liquid (IL) electrolyte, NaFSI/[PYR13] [FSI]. These changes increase the rate capability and capacity retention after cycling when compared Na 2 DBQ anodes using standard carbonate electrolytes. At 22 • C, the inclusion of the OMC leads to similar capacities for the IL-and carbonate-electrolytes, but the improved thermal stability of the IL enables safe operation at 60 • C, which more than doubles the discharge capacities due to enhanced ion mobility and charge transfer kinetics. At 60 • C, the capacity retention was 83% for the IL-electrolyte after 300 cycles. For the materials examined here, the use of IL electrolyte does not adversely impact the performance of organic anode sodium-ion batteries and provides advantages with a wider operating temperature range and improved safety when compared to typical carbonate-based electrolytes. The move toward clean energy technologies associated with electrical vehicles and renewable energy production requires energy storage systems that are safe, reliable and economical.1,2 Lithium ion batteries (LIBs) have dominated energy storage solutions for portable devices due to their high energy density (∼200 Wh/kg). 3 The need for improved performance has fueled significant efforts in new electrode materials to enhance the energy density of LIBs. 4,5 However, the growing demands for large-scale energy storage generate questions regarding the future availability and the cost of lithium, which could adversely impact the competitiveness of intermittent energy sources.6-8 Sodium with its orders of magnitude greater natural abundance compared to Li can potentially address these availability and cost concerns, 9 but the larger atomic size (Na + : 4.44 Å 3 and Li + : 1.84 Å 3 ) and higher intrinsic mass per charge of sodium leads to lower theoretical capacity for sodium ion batteries (SIBs) in comparison to LIBs. Challenges for SIBs include improving the reversible insertion electrode materials for Na + for enhanced discharge capacity and cyclability.10 In addition to the active materials for the electrodes, the selection of the electrolyte impacts performance, safety and cost. 11A variety of carbon materials, including ordered mesoporous ca...

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Section: Resultsmentioning

confidence: 99%

Enhanced Cycle Performance of Quinone-Based Anodes for Sodium Ion Batteries by Attachment to Ordered Mesoporous Carbon and Use of Ionic Liquid Electrolyte

Gurkan

Qiang

Chen

et al. 2017

J. Electrochem. Soc.

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“…However, this is only a crude estimate, and it should be possible to refine this value using the concept of "acceptor number." Jaworski and colleagues (18) showed that the redox potential of a quinone undergoing the first electron reduction in organic solvent is related to the electrophilic properties of the solvent. This work was based on a formulation by Gutman (19) of an acceptor number, a dimensionless number that expresses the acceptor properties of a given solvent relative to that of SbCl 5 .…”

Section: Discussionmentioning

confidence: 99%

Recruitment of a Foreign Quinone into the A1 Site of Photosystem I

Semenov¹,

Vassiliev²,

Est³

et al. 2000

Journal of Biological Chemistry

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Interruption of the menA or menB gene in Synechocystis sp. PCC 6803 results in the incorporation of a foreign quinone, termed Q, into the A 1 site of photosystem I with a number of experimental indicators identifying Q as plastoquinone-9. A global multiexponential analysis of time-resolved optical spectra in the blue region shows the following three kinetic components: 1) a 3-ms lifetime in the absence of methyl viologen that represents charge recombination between P700؉ and an FeS ؊ cluster; 2) a 750-s lifetime that represents electron donation from an FeS ؊ cluster to methyl viologen; and 3) an ϳ15-s lifetime that represents an electrochromic shift of a carotenoid pigment. Room temperature direct detection transient EPR studies of forward electron transfer show a spectrum of P700 ؉ Q ؊ during the lifetime of the spin polarization and give no evidence of a significant population of P700 ؉ FeS ؊ for t < 2-3 s. The UV difference spectrum measured 5 s after a flash shows a maximum at 315 nm, a crossover at 280 nm, and a minimum at 255 nm as well as a shoulder at 290 -295 nm, all of which are characteristic of the plastoquinone-9 anion radical. Kinetic measurements that monitor Q at 315 nm show a major phase of forward electron transfer to the FeS clusters with a lifetime of ϳ15 s, which matches the electrochromic shift at 485 nm of the carotenoid, as well as an minor phase with a lifetime of ϳ250 s. Electrometric measurements show similar biphasic kinetics. The slower kinetic phase can be detected using timeresolved EPR spectroscopy and has a spectrum characteristic of a semiquinone anion radical. We estimate the redox potential of plastoquinone-9 in the A 1 site to be more oxidizing than phylloquinone so that electron transfer from Q ؊ to F X is thermodynamically unfavorable in the menA and menB mutants.The overall goal of these studies is to replace phylloquinone (vitamin K 1 ; 2-methyl-3-phytyl-1,4-naphthoquinone) in the A 1 site of photosystem I with a foreign quinone of different redox and/or kinetic properties but still capable of forward electron transfer to the FeS 1 clusters. In two previous papers, we described the construction and physiology of phylloquinone biosynthetic mutants in Synechocystis sp. PCC 6803 (1), and we reported EPR and electron nuclear double resonance studies that implied the presence of a foreign quinone, termed Q, in the A 1 site of PS I (2). To summarize briefly, the interruption of the menA and menB genes, which code for dihydroxynaphthoic acid synthase and phytyltransferase, respectively, results in the termination of phylloquinone biosynthesis as judged by high pressure liquid chromatography/mass spectroscopy (HPLC/ MS) and gas chromatography/mass spectroscopy of pigment extracts from isolated PS I complexes. However, the menA and menB mutant strains grow photoautotrophically under low light intensities, and isolated PS I complexes are capable of sustaining high rates of steady-state electron transfer from cytochrome c 6 to flavodoxin. HPLC and HPLC/MS studies show that quantita...

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“…This shift can be explained by the higher AN for MeCN which solvates stronger, and therefore stabilize more, the anions. 54 In CO 2 ─saturated solutions (Blue lines in Figure 4a), little change was found for the reduction potentials and peak intensities for the first reduction waves, but positive shifts were observed for the second reduction waves, revealing the chemical reaction of Q 2¯ with CO 2 . The positive shifts were in general more pronounced in MeCN than in DMF, indicating a more stable adduct of Q 2¯ and CO 2 was formed in MeCN (Table S1).…”

Section: Figure 1 Chemical Structure Of the Herein Investigated Quinonesmentioning

confidence: 96%

Electrochemical Reduction of CO₂ Mediated by Quinone Derivatives: Implication for Li–CO₂ Battery

et al. 2018

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The pivotal role of CO 2 played in global temperature cycles has motivated the ongoing research on carbon capture and storage (CCS). Within this context, Li─CO 2 battery, alike the configuration of Li─O 2 battery, has been proposed as a novel energy storage device with the potential to reduce CO 2. Nevertheless, the highly negative potential required for the electrochemical reduction of CO 2 adds difficulty to the achievement of energy efficient Li─CO 2 battery. Facilitating the electron transfer to this inert molecule, which largely dictates the discharge voltage and rate capability of a Li─CO 2 battery, is therefore necessary. Herein three types of quinones have been surveyed aiming to mediate the reduction of CO 2 , which is expected to result in lower overpotential than with a direct electron transfer. We demonstrate by cyclic voltammetry that, in the presence of quinones, CO 2 reduction proceeds through an intermolecular interaction between CO 2 and quinone dianion. Importantly, such catalytic CO 2 reduction reaction is associated with the molecular structure of quinones, the supporting cation (e.g. Li +), and the electrolyte solvent. Furthermore, Li─CO 2 battery mediated by 2, 5-di-tertbutyl-1, 4-benzoquinone with Li 2 CO 3 as the ultimate discharge product is achieved. This study validates the concept of using quinones as chemical catalysts to promote CO 2 reduction in Li─CO 2 battery. Besides, battery performance and NMR analysis together suggest that side reactions involving quinone itself and/or other cell components occur.

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Solvent effect on the redox potential of quinone-semiquinone systems

Cited by 56 publications

References 16 publications

Enhanced Cycle Performance of Quinone-Based Anodes for Sodium Ion Batteries by Attachment to Ordered Mesoporous Carbon and Use of Ionic Liquid Electrolyte

Enhanced Cycle Performance of Quinone-Based Anodes for Sodium Ion Batteries by Attachment to Ordered Mesoporous Carbon and Use of Ionic Liquid Electrolyte

Recruitment of a Foreign Quinone into the A1 Site of Photosystem I

Electrochemical Reduction of CO₂ Mediated by Quinone Derivatives: Implication for Li–CO₂ Battery

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Solvent effect on the redox potential of quinone-semiquinone systems

Cited by 56 publications

References 16 publications

Enhanced Cycle Performance of Quinone-Based Anodes for Sodium Ion Batteries by Attachment to Ordered Mesoporous Carbon and Use of Ionic Liquid Electrolyte

Enhanced Cycle Performance of Quinone-Based Anodes for Sodium Ion Batteries by Attachment to Ordered Mesoporous Carbon and Use of Ionic Liquid Electrolyte

Recruitment of a Foreign Quinone into the A1 Site of Photosystem I

Electrochemical Reduction of CO2 Mediated by Quinone Derivatives: Implication for Li–CO2 Battery

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Electrochemical Reduction of CO₂ Mediated by Quinone Derivatives: Implication for Li–CO₂ Battery