Quinone and its derivatives for energy harvesting and storage materials

Son, Eun Jin; Kim, Jae Hong; Kim, Kayoung; Park, Chan Beum

doi:10.1039/c6ta03123d

Cited by 247 publications

(172 citation statements)

References 245 publications

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“…[167][168][169][170][171] [9][10][11][12][13][14][15][16][17][18][19][20][21], were proposed by Tarascon's group. [167][168][169][170][171] [9][10][11][12][13][14][15][16][17][18][19][20][21], were proposed by Tarascon's group.…”

Section: Stability-orientedmentioning

confidence: 99%

“…Specifically, 8-19 demonstrated the highest average discharge voltage of 2.47 V (vs Li + /Li), and 8-17 exhibited capacity retentions of more than 90% after 100 cycles at various rates. For example, introducing polyethylene oxide (PEO) into PIs(8)(9)(10)(11)(12)(13)(14)(15)(16)20) could eliminate the use of binders and reduce the use of conductive carbon (15 wt%), which not only Adv.Mater. For example, introducing polyethylene oxide (PEO) into PIs(8)(9)(10)(11)(12)(13)(14)(15)(16)20) could eliminate the use of binders and reduce the use of conductive carbon (15 wt%), which not only Adv.Mater.…”

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Molecular Engineering with Organic Carbonyl Electrode Materials for Advanced Stationary and Redox Flow Rechargeable Batteries

2017

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Organic carbonyl electrode materials that have the advantages of high capacity, low cost and being environmentally friendly, are regarded as powerful candidates for next-generation stationary and redox flow rechargeable batteries (RFBs). However, low carbonyl utilization, poor electronic conductivity and undesired dissolution in electrolyte are urgent issues to be solved. Here, we summarize a molecular engineering approach for tuning the capacity, working potential, concentration of active species, kinetics, and stability of stationary and redox flow batteries, which well resolves the problems of organic carbonyl electrode materials. As an example, in stationary batteries, 9,10-anthraquinone (AQ) with two carbonyls delivers a capacity of 257 mAh g (2.27 V vs Li /Li), while increasing the number of carbonyls to four with the formation of 5,7,12,14-pentacenetetrone results in a higher capacity of 317 mAh g (2.60 V vs Li /Li). In RFBs, AQ, which is less soluble in aqueous electrolyte, reaches 1 M by grafting -SO H with the formation of 9,10-anthraquinone-2,7-disulphonic acid, resulting in a power density exceeding 0.6 W cm with long cycling life. Therefore, through regulating substituent groups, conjugated structures, Coulomb interactions, and the molecular weight, the electrochemical performance of carbonyl electrode materials can be rationally optimized. This review offers fundamental principles and insight into designing advanced carbonyl materials for the electrodes of next-generation rechargeable batteries.

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Section: Stability-orientedmentioning

confidence: 99%

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confidence: 99%

Molecular Engineering with Organic Carbonyl Electrode Materials for Advanced Stationary and Redox Flow Rechargeable Batteries

2017

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“…Additionally, their electron acceptor and donor properties can be fine‐tuned by varying the substituent groups on the central ring and by adjusting the properties of their immediate environment, for example through hydrogen bonding interactions in a protein pocket. It is not surprising that these features make quinones attractive also in artificial photosynthesis and in technological applications such as functionalization of materials developed for energy harvesting and storage …”

Section: Introductionmentioning

confidence: 99%

Systematic High‐Accuracy Prediction of Electron Affinities for Biological Quinones

2018

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Quinones play vital roles as electron carriers in fundamental biological processes; therefore, the ability to accurately predict their electron affinities is crucial for understanding their properties and function. The increasing availability of cost-effective implementations of correlated wave function methods for both closed-shell and open-shell systems offers an alternative to density functional theory approaches that have traditionally dominated the field despite their shortcomings. Here, we define a benchmark set of quinones with experimentally available electron affinities and evaluate a range of electronic structure methods, setting a target accuracy of 0.1 eV. Among wave function methods, we test various implementations of coupled cluster (CC) theory, including local pair natural orbital (LPNO) approaches to canonical and parameterized CCSD, the domainbased DLPNO approximation, and the equations-of-motion approach for electron affinities, EA-EOM-CCSD. In addition, several variants of canonical, spin-component-scaled, orbital-optimized, and explicitly correlated (F12) Møller-Plesset perturbation theory are benchmarked. Achieving systematically the target level of accuracy is challenging and a composite scheme that combines canonical CCSD(T) with large basis set LPNObased extrapolation of correlation energy proves to be the most accurate approach. Methods that offer comparable performance are the parameterized LPNO-pCCSD, the DLPNO-CCSD(T 0 ), and the orbital optimized OO-SCS-MP2. Among DFT methods, viable practical alternatives are only the M06 and the double hybrids, but the latter should be employed with caution because of significant basis set sensitivity. A highly accurate yet cost-effective DLPNO-based coupled cluster approach is used to investigate the methoxy conformation effect on the electron affinities of ubiquinones found in photosynthetic bacterial reaction centers.

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“…[6][7][8] In this context, substituting traditional metal-based intercalation compounds by redox-active polymers (RAPs) with electroactive organic redox functionalities have attracted the attention of researchers due to the greater abundance of organic compounds, huge synthetic possibilities, lower-cost, and sustainability. [15][16][17] In particular, within the family of quinones, anthraquinone-based polymers have demonstrated superior electrochemical performance, exhibiting enhanced (electro)chemical stability, high active-material utilization and facilitated redox kinetics. [9][10][11][12][13][14] Among the vast variety of organic redox-active groups (nitroxyl, phenoxyl, quinones, viologens, carbazol, etc.…”

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confidence: 99%

New Anthraquinone‐Based Conjugated Microporous Polymer Cathode with Ultrahigh Specific Surface Area for High‐Performance Lithium‐Ion Batteries

Molina

Patil

Ventosa

et al. 2019

Adv Funct Materials

109

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Redox-active conjugated microporous polymers (RCMPs) polymerized by conventional methods are commonly obtained as irregular insoluble solid particles making the electrode processing difficult. In this work, the synthesis of RCMP based on anthraquinone moieties (IEP-11) is developed via a two-step pathway combining miniemulsion and solvothermal techniques that results in polymer nanostructures that are much easier to disperse in solvents facilitating the fabrication of electrodes. Interestingly, this synthetic approach is also found to have an important impact on the inherent morphology of IEP-11 that exhibits a dual porosity combining micro and mesopores with a specific surface area as high as 2200 m 2 g −1 , which is one of the highest values reported for RCMPs. Moreover, the compactness of the electrodes is also improved, the resulting electrodes have triple the density than those obtained with conventional methods. Consequently, when these electrodes are tested as cathodes in Li-ion battery, they deliver high gravimetric capacities (≈100 mAh g −1 ) and extraordinary rate capability keeping 76% of discharge capacity when charged-discharged in only 12 min (@5 C). Moreover, the insoluble and robust conjugated porous structure provides IEP-11-E12 with an unprecedented cycling stability retain ≈90% and ≈60% of its initial capacity after 5000 (@2 C) and 80 000 cycles (@30 C), respectively.

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Quinone and its derivatives for energy harvesting and storage materials

Abstract: Recent advances in the design of quinone-functionalized hybrid materials are reviewed based on quinone's redox, electrical, optical, and metal chelating/reducing properties to determine these materials' applications in energy harvesting and storage systems.

Cited by 247 publications

References 245 publications

Molecular Engineering with Organic Carbonyl Electrode Materials for Advanced Stationary and Redox Flow Rechargeable Batteries

Molecular Engineering with Organic Carbonyl Electrode Materials for Advanced Stationary and Redox Flow Rechargeable Batteries

Systematic High‐Accuracy Prediction of Electron Affinities for Biological Quinones

New Anthraquinone‐Based Conjugated Microporous Polymer Cathode with Ultrahigh Specific Surface Area for High‐Performance Lithium‐Ion Batteries

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