A Tris-fused Tetrathiafulvalene Analog Composed of an Anthraquinoid- and Two Vinyl-extended Tetrathiafulvalenes

Oshima, Toko; Sasaki, Ami; Yamauchi, Tomokazu; Yoshimura, Aya; Shirahata, Takashi; Yao, Masaru; Misaki, Yohji

doi:10.1246/cl.210070

Cited by 8 publications

(3 citation statements)

References 34 publications

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“…In a previous study, we found that TTF-4TPA acts as an active material . CV of TTF alone and reports on molecules containing it suggest that it can act as an active material. − However, the possible function of the TPA moiety as an active substance remains unclear, and its in-cell polymerization has not been reported. Therefore, the charge/discharge curves and cycle performance of the cell with TPA were investigated in a Li system, as shown in Figure .…”

Section: Resultsmentioning

confidence: 93%

Cation-Independent Anion Battery Using Organic Cathodes Utilizing a Triphenylamine Moiety for In-Cell Electropolymerization

Sano,

Yoshimura,

Zhang

et al. 2024

ACS Appl. Polym. Mater.

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Lithium-ion batteries have become the dominant technology for portable electronics and electric vehicles over the past few decades; however, high costs and limited resources have prompted the need for alternative materials. Organic batteries made of abundant and inexpensive materials have the potential to address these challenges. Our previous study focused on tetrathiafulvalene (TTF) bearing triphenylamine (TPA) moieties, TTF-4TPA, wherein TTF exhibits redox activity and TPA shows both polymerization properties and redox activity. Polymerization of active material molecules contributes to long cyclability. TTF-4TPA has been reported to polymerize during the first charge and exhibit high cyclability thereafter. This study investigated the electrochemical properties of a TTF-4TPA-based organic battery. The TTF-4TPA battery was found to exhibit excellent rate performance in a Li-ion system. Moreover, the TTF-4TPA battery was found to be operable even in a Na-ion system.

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Section: Resultsmentioning

confidence: 93%

Cation-Independent Anion Battery Using Organic Cathodes Utilizing a Triphenylamine Moiety for In-Cell Electropolymerization

Sano,

Yoshimura,

Zhang

et al. 2024

ACS Appl. Polym. Mater.

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“…Among the redox-active organic molecules, tetrathiafulvalene (TTF) and its vinyl analogue, ethanediylidene-2,2′-bis(1,3-dithiole) (EBDT) (Figure ), are superior active materials in terms of their theoretical capacities and redox potentials. , Unfortunately, pristine TTF and EBDT are soluble in organic electrolytes. Our group has developed many fused donors comprising TTF and/or EBDT to attempt lowering the solubility via increasing the size and planarity of the molecules and intermolecular interactions. − However, producing slightly soluble TTFs and EBDTs for organic electrolytes remains elusive. Although one approach to solving the solubility issue is to use polymers grafted onto redox sites, the required redox-inactive linkage usually leads to decreased capacity. , …”

Section: Introductionmentioning

confidence: 99%

Improvement in Cycle Life of Organic Lithium-Ion Batteries by In-Cell Polymerization of Tetrathiafulvalene-Based Electrode Materials

Yoshimura

Hemmi

Moriwaki

et al. 2022

ACS Appl. Mater. Interfaces

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Redox-active organic molecules are promising candidates for next-generation electrode materials. Nevertheless, finding low-molecular-weight organic materials with a long cycle life remains a crucial challenge. Herein, we demonstrate the application of tetrathiafulvalene and its vinyl analogue bearing triphenylamines as long-cycle-life electrodes for lithium-ion batteries (LIBs). These molecules were successfully synthesized using palladium-catalyzed C–H arylation. Electrochemical analysis revealed that a polymer formed on the electrode. LIBs comprising these molecules exhibited noteworthy charge–discharge properties with a long cycle life (the capacity after 100 cycles was greater than 90% of the discharge capacity in the third cycle) and a high utilization ratio (approximately 100%). “In-cell” polymerization during the first charge process is considered to contribute to the effect. This study indicates new avenues for the creation of organic materials for rechargeable batteries.

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“…Our research group has sought to lower the solubility of redox-active tetrathiafulvalene (TTF) analogs 8 by increasing the size and planarity of the molecules and intermolecular interactions. [9][10][11][12][13][14][15][16][17][18] Recently, we have successfully demonstrated the application of TTF bearing triphenylamines (TTF-4TPA, Fig. 1) as long-cycle-life electrodes for LIBs via the ''in-cell polymerization'' technique.…”

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confidence: 99%

Synthesis of Bz-TTFs with polymerization sites and the properties of Li-ion batteries comprising them as active materials

Yoshimura,

Yoshinouchi,

Hemmi

et al. 2023

New J. Chem.

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A Tris-fused Tetrathiafulvalene Analog Composed of an Anthraquinoid- and Two Vinyl-extended Tetrathiafulvalenes

Cited by 8 publications

References 34 publications

Cation-Independent Anion Battery Using Organic Cathodes Utilizing a Triphenylamine Moiety for In-Cell Electropolymerization

Cation-Independent Anion Battery Using Organic Cathodes Utilizing a Triphenylamine Moiety for In-Cell Electropolymerization

Improvement in Cycle Life of Organic Lithium-Ion Batteries by In-Cell Polymerization of Tetrathiafulvalene-Based Electrode Materials

Synthesis of Bz-TTFs with polymerization sites and the properties of Li-ion batteries comprising them as active materials

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