Fused Tetrathiafulvalene and Benzoquinone Triads: Organic Positive‐Electrode Materials Based on a Dual Redox System

Misaki, Yohji; Noda, Shigenobu; Kato, Masaru; Yamauchi, Tomokazu; Oshima, Toko; Yoshimura, Aya; Shirahata, Takashi; Yao, Masaru

doi:10.1002/cssc.202000178

Cited by 27 publications

(11 citation statements)

References 55 publications

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“…The chemistry of quinones and their derivatives has been studied for over 80 years and, recently, these molecules have received renewed interest in material chemistry due to their “ non-innocent ” behavior ( vide supra ) and inherent redox activity. 54,63,77–80 In fact, benzoquinones can undergo a one-electron reversible reduction which leads to the formation of a semiquinone species that can be further reduced to hydroquinone. These reversible reactions make this class of molecules ideal candidates as building blocks for constructing switchable materials, where magnetic and/or conducting properties can be tuned by switching quinone–semiquinone species.…”

Section: Redox Activity Of Quinonesmentioning

confidence: 99%

Redox-active benzoquinones as challenging “non-innocent” linkers to construct 2D frameworks and nanostructures with tunable physical properties

et al. 2022

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Section: Redox Activity Of Quinonesmentioning

confidence: 99%

Redox-active benzoquinones as challenging “non-innocent” linkers to construct 2D frameworks and nanostructures with tunable physical properties

et al. 2022

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“…It has been widely used in field-effect transistors, dye-sensitized solar cells, electrochromic devices, and molecular machines and is a promising candidate for both solid-state and liquid-state organic batteries. − For solid-state battery applications, the solubility of TTF in electrolytes needs to be as low as possible. Misaki et al used oligomerization of TTF to lower its solubility in organic electrolytes and achieved improved cycling stability . For liquid-state RFB applications, the solubility of TTF in electrolytes needs to be as high as possible.…”

Section: Introductionmentioning

confidence: 99%

Highly Soluble Dimethoxymethyl Tetrathiafulvalene with Excellent Stability for Non-Aqueous Redox Flow Batteries

Chen

Shen

Chen

et al. 2023

ACS Appl. Mater. Interfaces

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Non-aqueous redox flow batteries (RFBs) are highly attractive for grid-scale energy storage applications because of their independent design of energy and power, high energy density and efficiency, easy maintenance, and potentially low cost. In order to develop active molecules with large solubility, excellent electrochemical stability, and high redox potential for a nonaqueous RFB catholyte, herein, two flexible methoxymethyl groups had been attached to a famous redox-active tetrathiafulvalene (TTF) core. The strong intermolecular packing of the rigid TTF unit was effectively depressed, leading to a dramatically improved solubility of up to 3.1 M in conventional carbonate solvents. The performance of the obtained dimethoxymethyl TTF (DMM-TTF) was studied in a semi-solid RFB system with Li foil as the counter electrode. When using porous Celgard as the separator, the hybrid RFB with 0.1 M DMM-TTF had two high discharge plateaus at 3.20 and 3.52 V and a low capacity retention of 30.7% after 100 cycles at 5 mA cm −2 . Replacing Celgard with a permselective membrane, the capacity retention was increased to 85.4%. Further increasing the concentration of DMM-TTF to 1.0 M and current density to 20 mA cm −2 , the hybrid RFB exhibited a high volumetric discharge capacity of 48.5 A h L −1 and an energy density of 154 W h L −1 . The capacity was maintained at 72.2% after 100 cycles (10.7 days). The great redox stability of DMM-TTF was revealed by UV−vis and 1 H NMR tests and verified by density functional theory calculations. Therefore, the methoxymethyl group is an excellent group to increase the solubility while maintaining the redox capability of TTF for high-performance non-aqueous RFBs.

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“…[27][28][29][30] TTF and its derivatives are known to afford a great number of molecular conductors with metal conductivity. [31][32][33] The redox of TTF units can be used to store energy [34][35][36][37] and TTF as an additive can effectively improve the cycle performance of LiÀ O 2 and lithium-ion batteries. [38][39][40] However, the application of TTF as a conjugated platform for the development of organic anode materials has not be reported yet.…”

Section: Introductionmentioning

confidence: 99%

Conjugated Tetrathiafulvalene Carboxylates for Stable Organic Lithium Batteries

Chen

et al. 2022

ChemElectroChem

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Organic electrode materials are potential energy storage materials for the next generation lithium batteries. Herein, carboxylate groups are installed to a conjugated tetrathiafulvalene (TTF) platform to yield two compounds, namely lithium tetrathiafulvalene‐dicarboxylate (TTF‐Li2) and lithium tetrathiafulvalene‐tetracarboxylate (TTF‐Li4), as stable anode materials for lithium batteries. The low solubility in the electrolyte, brought about by the carboxylate groups, and high rechargeability ensured by the conjugated TTF platform lead to excellent battery performance. After cycling at a current density of 0.5 C for 120 cycles, a net specific capacity of 108.19 mAh g−1 and 217.55 mAh g−1 is obtained for the TTF‐Li2 and TTF‐Li4 anodes containing 70 wt.% of active materials, corresponding to 61.4 % and 82.0 % of their theoretical capacities, respectively. The density functional theory (DFT) calculation confirms the well‐delocalized charge for both TTF‐Li2 and TTF‐Li4. Therefore, the TTF‐Li2 and TTF‐Li4 are promising anode materials for lithium batteries.

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Fused Tetrathiafulvalene and Benzoquinone Triads: Organic Positive‐Electrode Materials Based on a Dual Redox System

Cited by 27 publications

References 55 publications

Redox-active benzoquinones as challenging “non-innocent” linkers to construct 2D frameworks and nanostructures with tunable physical properties

Redox-active benzoquinones as challenging “non-innocent” linkers to construct 2D frameworks and nanostructures with tunable physical properties

Highly Soluble Dimethoxymethyl Tetrathiafulvalene with Excellent Stability for Non-Aqueous Redox Flow Batteries

Conjugated Tetrathiafulvalene Carboxylates for Stable Organic Lithium Batteries

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