Synthesis and investigation of a new organic electrode material based on condensation product of triquinoyl with 1,2,4,5-tetraaminobenzene

Baymuratova, G. R.; Khatmullina, K. G.; Yakuschenko, Igor K.; Tulibaeva, G. Z.; Savinykh, T. A.; Troshin, Pavel A.; Shestakov, Alexander F.; Yarmolenko, O. V.

doi:10.1016/j.jelechem.2021.115234

Cited by 6 publications

(9 citation statements)

References 22 publications

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“…Nietzki (1847–1917) is an unfamiliar figure to many modern organic chemists, but he made farsighted contributions in areas of enduring importance. − Nietzki’s impact can be measured by the frequency with which compounds first made in his research group are used today. In particular, BTA ( 1 ) and its derivatives are at the center of an imposing array of projects, including studies in which the compounds are used as precursors of redox-active materials, − ligands in coordination chemistry, − components for making metal–organic frameworks (MOFs) and covalent organic frameworks (COFs) by modular construction, − monomers for producing polymers, − components of switches and sensors, , precursors for synthesizing diverse heterocyclic compounds, − and enzyme inhibitors for use in treating cancer …”

Section: Introductionmentioning

confidence: 99%

Refreshing the Legacy of Rudolf Nietzki: Benzene-1,2,4,5-tetramine and Related Compounds

Sosoe,

Malveau,

Maris

et al. 2023

J. Org. Chem.

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Like hydroquinones and quinones, aromatic compounds with multiple NH2 groups and the corresponding quinonediimines have the potential to serve as components of useful redox-active organic materials. Benzene-1,2,4,5-tetramine (BTA) and its oxidized form BTA-H2 offer a promising redox pair of this type, and the compounds have proven to be useful in many areas of chemistry. However, key aspects of their behavior have remained poorly studied, such as the nature of their protonated forms, their preferred molecular structures, their reactivity, and their organization in condensed phases. In the present work, we have used a combination of improved methods of synthesis, computation, spectroscopic studies, and structural analyses to develop a deeper understanding of BTA, BTA-H2, their salts, and related compounds. The new knowledge is expected to accelerate exploitation of the compounds in areas of materials science where desirable properties can only be attained by properly controlling the organization of molecular components.

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Section: Introductionmentioning

confidence: 99%

Refreshing the Legacy of Rudolf Nietzki: Benzene-1,2,4,5-tetramine and Related Compounds

Sosoe,

Malveau,

Maris

et al. 2023

J. Org. Chem.

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“…Scheme 1 shows the electrochemical redox transformation of PTTA accompanying the charge and discharge of the cell, which follows from the quantum chemical calculations [20].…”

Section: Resultsmentioning

confidence: 99%

“…Previously, in the study of PTTA in lithium cells [20], an unexpectedly strong effect of the addition of 5 wt% benzo-15-crown-5 in 1 M LiPF6 in EC/DMC (1:1 v/v) was found. For example, it was shown in [20] that the discharge capacity of PTTA increased by a factor of 3 (344 mAh g −1 ) in the presence of only 5 wt% crown ether in the electrolyte composition. It is known that crown ethers can "extract" metal ions from solvate shells of solvents [23][24][25].…”

Section: Ventsmentioning

confidence: 91%

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Influence of the Lithium Cation Desolvation Process at the Electrolyte/Electrode Interface on the Performance of Lithium Batteries

et al. 2022

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The article considers the effect of the solvate environment of the lithium cation in various aprotic solvents.The redox reactions of electrodes made from a polymeric condensation product of triquinoyl with 1,2,4,5-tetraaminobenzene are studied. A 1 M LiPF6 solution was used as an electrolyte, in either ethylene carbonate/dimethyl carbonate (EC/DMC) or tetraglyme. Based on the electrochemical studies and quantum chemical modeling, it was shown that the desolvation of lithium cations in the tetraglyme-based electrolyte makes it possible to obtain a capacity close to the theoretical one (up to 546 mAh g−1) and only 125 mAh g−1 for the EC/DMC electrolyte. This decrease is due to the fact that the lithium cation adds to the functional groups of the organic material with two dimethyl carbonate molecules, as well as the PF6- anion.

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“…Selecting 1,2,4,5-BTA ( 1 ) for detailed study is warranted because the compound is at the center of an impressive range of projects in which it is used as a precursor of redox-active materials, − a ligand in coordination chemistry, − a component of metal–organic frameworks (MOFs) and covalent organic frameworks (COFs), − a monomer for producing polymers, − a component of switches and sensors, , a precursor for synthesizing diverse heterocyclic compounds, − and an enzyme inhibitor for use in treating cancer . However, fuller exploitation of 1,2,4,5-BTA ( 1 ) and analogues such as 1,2,3,4-BTA ( 3 ) will require a better understanding of their fundamental properties, such as the nature of their salts and their preferred patterns of association in the solid state, which will determine how they are best used as the components of redox-active materials.…”

Section: Introductionmentioning

confidence: 99%

Strongly Hydrogen-Bonded Networks Formed by Sulfate and Bisulfate Salts of Benzenetetramines

Sosoe,

Maris,

Wuest

2023

Crystal Growth & Design

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Benzenetetramines, like other aromatic compounds with multiple NH2 groups, are easily oxidized and are attractive candidates for use as components of redox-active organic materials. However, many aspects of the chemistry of benzenetetramines and related compounds remain poorly understood, such as the nature of their salts and their preferred patterns of association, which determine how they can be used to construct predictably ordered redox-active solids. To provide relevant new information, we have studied a series of sulfate and bisulfate salts of the 1,2,4,5- and 1,2,3,4-isomers, which have been found to crystallize as strongly hydrogen-bonded networks. The results of this work promise to facilitate the use of benzenetetramines and other complex arylamines as components of redox-active organic solids.

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Synthesis and investigation of a new organic electrode material based on condensation product of triquinoyl with 1,2,4,5-tetraaminobenzene

Cited by 6 publications

References 22 publications

Refreshing the Legacy of Rudolf Nietzki: Benzene-1,2,4,5-tetramine and Related Compounds

Refreshing the Legacy of Rudolf Nietzki: Benzene-1,2,4,5-tetramine and Related Compounds

Influence of the Lithium Cation Desolvation Process at the Electrolyte/Electrode Interface on the Performance of Lithium Batteries

Strongly Hydrogen-Bonded Networks Formed by Sulfate and Bisulfate Salts of Benzenetetramines

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