Naphthalene Diimide Based Materials with Adjustable Redox Potentials: Evaluation for Organic Lithium-Ion Batteries

Vadehra, Geeta S.; Maloney, Ryan; Garcı́a-Garibay, Miguel A.; Dunn, Bruce

doi:10.1021/cm503800r

Cited by 146 publications

(150 citation statements)

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“…[77,[97][98][99][100][101][102] For example, Vadehra et al systematically studied a series of naphthalene diimidebased materials. [77,[97][98][99][100][101][102] For example, Vadehra et al systematically studied a series of naphthalene diimidebased materials.…”

Section: Working-potential-orientedmentioning

confidence: 99%

“…Carbonyl compounds indeed possess fast reaction kinetics but generally experience poor rate performance due to their intrinsic low electronic conductivity. Structure, theoretical capacities and first reduction voltage (vs Li + /Li) of a) naphthalene diimide-based materials with different substituent groups, [97] b) AQ and its heteroatom-ring analogue (PID), [104] c) PQ and its two N-substituted analogues, [107] d) Li 4 -p-DHT and Li 4 -o-DHT. [110] Theoretically, the electron conductivity of organic molecules could also be adjusted by molecular engineering.…”

Section: Kinetics-orientedmentioning

confidence: 99%

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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: Working-potential-orientedmentioning

confidence: 99%

Section: Kinetics-orientedmentioning

confidence: 99%

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

2017

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“…[21] As ac lassic organic sodium-ion battery anode,the sodium salt of terephthalate (PTA-Na, compound a in Figure 1) has ac apacity of 295 mAh g À1 at ac urrent density of 0.1 C( 30 mA g À1 ), [16,21] which is comparable to the commonly available hard carbon anodes (ca. [21,26,27] Thel imitation of these functional groups is that they can only store one sodium ion reversibly,w hich results in ac apacity that is strongly limited by the molecular weight of the molecule. [25] Up to now,m ost of the organic sodium-ion electrodes are composed of oxygen-containing functional groups (carboxylate and carbonyl groups).…”

mentioning

confidence: 99%

Organic Thiocarboxylate Electrodes for a Room‐Temperature Sodium‐Ion Battery Delivering an Ultrahigh Capacity

et al. 2017

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Organic room-temperature sodium-ion battery electrodes with carboxylate and carbonyl groups have been widely studied. Herein, for the first time,wereport afamily of sodiumion battery electrodes obtained by replacing stepwise the oxygen atoms with sulfur atoms in the carboxylate groups of sodium terephthalate whichi mproves electron delocalization, electrical conductivity and sodium uptake capacity.T he versatile strategy based on molecular engineering greatly enhances the specific capacity of organic electrodes with the same carbon scaffold. By introducing two sulfur atoms to as ingle carboxylates caffold, the molecular solid reaches ar eversible capacity of 466 mAh g À1 at ac urrent density of 50 mA g À1 .When four sulfur atoms are introduced, the capacity increases to 567 mAh g À1 at ac urrent density of 50 mA g À1 , which is the highest capacity value reported for organic sodium-ion battery anodes until now.Organic battery electrodes are alternatives to traditional metal-oxide electrode materials due to their low costs, absence of heavy metals and easily tunable structures. [1][2][3][4][5][6][7][8][9][10][11][12][13][14][15] Generally,o rganic electrodes accommodate redox centers and alkali-metal ions by functional groups such as carboxylate, [16] carbonyl, [17] organodisulfide, [18] thioether [19] and nitroxyl radicals, [20] while the aromatic cores donate or accept electrons during the redox process. [19] Carboxylate groups are usually applied as lithium/sodium anodes which reversibly store/release Li + /Na + ions through at wo-electron process. [21,22] In the case of alithium-ion anode,far more than two Li + ions can be stored in the carboxylate molecule under deep discharge, [23,24] which leads to the high capacity of organic lithium anodes.H owever,f or sodium-ion battery cells,there is no evidence of super-sodiation. Thesodium ion is larger and less electronegative than the lithium ion.Even though the organic sodium-ion battery has al ower specific capacity than the lithium-ion battery,the sodium-ion battery is attractive because of the less rigid lattice compared with metal-oxide lattices,w hich can accommodate the large sodium ions so that the rate capability and cycle stability are advantageous. [21] As ac lassic organic sodium-ion battery anode,the sodium salt of terephthalate (PTA-Na, compound a in Figure 1) has ac apacity of 295 mAh g À1 at ac urrent density of 0.

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“…Aiming to increase the voltage of NDI s in lithium‐ion batteries, Dunn and co‐workers introduced substituents with different electronic effects onto the NDI core. Compounds with electron donating groups −NMe 2 ( 16 and 23 ) and electron withdrawing −F ( 17 ) and −CN ( 18 and 22 ) were considered . The synthetic routes to prepare different NDI derivatives are described in Scheme .…”

Section: Redox‐active Carbonyl‐based π‐Conjugated Small Molecules Formentioning

confidence: 99%

Carbonyl‐Based π‐Conjugated Materials: From Synthesis to Applications in Lithium‐Ion Batteries

Oubaha

Melinte

2019

ChemPlusChem

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The constant growth in the global energy demand together with the increasing awareness of clean and sustainable development has strongly pushed scientists to search for metal‐free, low‐cost, environmentally friendly functional energy‐storage systems (ESSs). Among the reported organic electrode materials, carbonyl‐based π‐conjugated compounds show excellent rate capabilities and cycling stabilities and are powerful candidates for the next generation of rechargeable lithium‐ion batteries (LIBs). Benefiting from the molecular structure versatility and design feasibility, the electrochemical properties of organic and polymeric materials can be easily tuned. This Review summarizes recent efforts in the search for carbonyl‐based π‐conjugated electrode materials in LIBs with a focus on the synthetic strategies developed to improve their electrochemical performance. The use of these materials in flexible, all‐organic LIBs is highlighted as a unique direction towards widespread applications of LIBs.

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Naphthalene Diimide Based Materials with Adjustable Redox Potentials: Evaluation for Organic Lithium-Ion Batteries

Cited by 146 publications

References 23 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

Organic Thiocarboxylate Electrodes for a Room‐Temperature Sodium‐Ion Battery Delivering an Ultrahigh Capacity

Carbonyl‐Based π‐Conjugated Materials: From Synthesis to Applications in Lithium‐Ion Batteries

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