Lithiated 1,4,5,8-Naphthalenetetraol Formaldehyde Polymer, An Organic Cathode Material

Kassam, Adil; Burnell, D. Jean; Dahn, J. R.

doi:10.1149/1.3516954

Cited by 29 publications

(28 citation statements)

References 6 publications

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“…A noticeable decrease in capacity on cycling was also noticed due to certain solubility in the electrolyte, which can partly be suppressed by simply adding γ‐Al 2 O 3 nanoparticles to the composite electrode; this suggests that much better performance can be expected by designing efficient composite electrodes. As previously observed by Dahn et al 8. for a polymer based on a lithiated naphthazarin unit, the reversible deintercalation process occurring in Li 2 DHDMQ (System 1) also suffers from quite large polarization.…”

Section: Resultssupporting

confidence: 64%

“…reported no electrochemical response for parent structure Li 2 H 2 C 6 O 4 (Figure 1 a). Dahn and co‐workers8 recently reported a polymer based on a lithiated naphthazarin unit that reacts at an average potential of 3 V, but this material exhibits limited electrochemical performance coupled with an intriguingly high polarization value (i.e., charge/discharge potential difference).…”

Section: Introductionmentioning

confidence: 99%

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High‐Potential Reversible Li Deintercalation in a Substituted Tetrahydroxy‐p‐benzoquinone Dilithium Salt: An Experimental and Theoretical Study

Barrès

Geng

Bonnard

et al. 2012

Chemistry A European J

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Efficient organic Li-ion batteries require air-stable lithiated organic structures that can reversibly deintercalate Li at sufficiently high potentials. To date, most of the cathode materials reported in the literature are typically synthesized in their fully oxidized form, which restricts the operating potential of such materials and requires use of an anode material in its lithiated state. Reduced forms of quinonic structures could represent examples of lithiated organic-based cathodes that can deintercalate Li(+) at potentials higher than 3 V thanks to substituent effects. Having previously recognized the unique electrochemical properties of the C(6)O(6)-type ring, we have now designed and then elaborated, through a simple three-step method, lithiated 3,6-dihydroxy-2,5-dimethoxy-p-benzoquinone, a new redox amphoteric system derived from the tetralithium salt of tetrahydroxy-p-benzoquinone. Electrochemical investigations revealed that such an air-stable salt can reversibly deintercalate one Li(+) ion on charging with a practical capacity of about 100 mAh g(-1) at about 3 V, albeit with a polarization effect. Better capacity retention was obtained by simply adding an adsorbing additive. A tetrahydrated form of the studied salt was also characterized by XRD and first-principles calculations. Various levels of theory were probed, including DFT with classical functionals (LDA, GGA, PBEsol, revPBE) and models for dispersion corrections to DFT. One of the modified dispersion-corrected DFT schemes, related to a rescaling of both van der Waals radii and s(6) parameter, provides significant improvements to the description of this kind of crystal over other treatments. We then applied this optimized approach to the screening of hypothetical frameworks for the delithiated phases and to search for the anhydrous structure.

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Section: Resultssupporting

confidence: 64%

Section: Introductionmentioning

confidence: 99%

High‐Potential Reversible Li Deintercalation in a Substituted Tetrahydroxy‐p‐benzoquinone Dilithium Salt: An Experimental and Theoretical Study

Barrès

Geng

Bonnard

et al. 2012

Chemistry A European J

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show abstract

“…[ 151,152 ] The cycle performance of 116 , ∼ 80% capacity retention after forty cycles, is acceptable (in comparison with the poor performance of the early compounds), but both the C theo (228 mAh g − 1 ) and discharge potential (2.3 V vs Li/Li + ) of 116 are lower than quinone 114 . Unfortunately, both the two polymers obtained with this method, the dihydroxybenzoquinone derivative 117 [ 158 ] and dihydroxynaphthoquinone derivative [ 159 ] (the structure of which polymer was not specifi ed) meet with low utilization of the active material (no more than one-electron exchange per monomer unit) and thus low capacities (100 − 120 mAh g − 1 ). From a structural point of view, the above polymers could be regarded as the result of electroactive molecular carbonyl compounds connected by NH groups.…”

Section: Reviewmentioning

confidence: 99%

Organic Electrode Materials for Rechargeable Lithium Batteries

Liang

Tao

Chen

2012

Advanced Energy Materials

1,193

1,016

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Organic compounds offer new possibilities for high energy/power density, cost-effective, environmentally friendly, and functional rechargeable lithium batteries. For a long time, they have not constituted an important class of electrode materials, partly because of the large success and rapid development of inorganic intercalation compounds. In recent years, however, exciting progress has been made, bringing organic electrodes to the attention of the energy storage community. Herein thirty years' research efforts in the fi eld of organic compounds for rechargeable lithium batteries are summarized. The working principles, development history, and design strategies of these materials, including organosulfur compounds, organic free radical compounds, organic carbonyl compounds, conducting polymers, non-conjugated redox polymers, and layered organic compounds are presented. The cell performances of these materials are compared, providing a comprehensive overview of the area, and straightforwardly revealing the advantages/disadvantages of each class of materials.

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“…In addition, the easily dissolved carbonyls (raw materials or radical products) are shuttled to the Li anode with side reactions, resulting in low Coulombic efficiency and poor cycling stability. One is by increasing the molecular weight through polymerization (Figure 8), [119][120][121][122][123][124][125][126][127] and the other is by enhancing the polarity through salt formation (Figure 9). Therefore, most research interests so far have focused on solving this problem and enhancing the stability of carbonyls and extending cycling life.…”

Section: Stability-orientedmentioning

confidence: 99%

“…[30] Two derivatives of 8-1, poly(2,5-dihydroxy-1,4-benzoquinone-3,6-methylene) (PDBM, [128] and lithiated 1,4,5,8-naphalenetetraol formaldehyde polymer (LNFP, the concrete structure was not given), [122] have also been assessed as electrode materials for LIBs, and some progress has been made in their cycling stability. [30] Two derivatives of 8-1, poly(2,5-dihydroxy-1,4-benzoquinone-3,6-methylene) (PDBM, [128] and lithiated 1,4,5,8-naphalenetetraol formaldehyde polymer (LNFP, the concrete structure was not given), [122] have also been assessed as electrode materials for LIBs, and some progress has been made in their cycling stability.…”

Section: Stability-orientedmentioning

confidence: 99%

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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Lithiated 1,4,5,8-Naphthalenetetraol Formaldehyde Polymer, An Organic Cathode Material

Cited by 29 publications

References 6 publications

High‐Potential Reversible Li Deintercalation in a Substituted Tetrahydroxy‐p‐benzoquinone Dilithium Salt: An Experimental and Theoretical Study

High‐Potential Reversible Li Deintercalation in a Substituted Tetrahydroxy‐p‐benzoquinone Dilithium Salt: An Experimental and Theoretical Study

Organic Electrode Materials for Rechargeable Lithium Batteries

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

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