Synthesis and solvent-free polymerisation of vinyl terephthalate for application as an anode material in organic batteries

Nauroozi, Djawed; Pejic, Marijana; Schwartz, Pierre-Olivier; Wachtler, Mario; Bäuerle, Peter

doi:10.1039/c6ra24064j

Cited by 15 publications

(12 citation statements)

References 32 publications

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“…After stirring at À78 8Cf or 2.5 h, dry DMF (6.00 mL, 77.5 mmol) was slowly added, and the reaction mixture was stirred at room temperature for 2. [(1E,3Z,5Z,7Z)-Cycloocta-1,3,5,7-tetraen-1-yl]methanol (9):N aBH 4 (50.9 mg, 1.34 mmol) was added to as olution of (1E,3Z,5Z,7Z)-cycloocta-1,3,5,7-tetraene-1-carbaldehyde (350 mg, 2.69 mmol) in THF (8 mL) [(1E,3Z,5Z,7Z)-Cycloocta-1,3,5,7-tetraen-1-yl]methyl acetate (4): 4-Dimethylaminopyridine (3.2 mg, 26 mmol) and acetic anhydride (74 mL, 782 mmol) were added to as olution of [(1E,3Z,5Z,7Z)-cycloocta-1,3,5,7-tetraen-1-yl]methanol (9,1 00 mg, 745 mmol) in dry pyridine (5 mL). The reaction mixture was stirred at room temperature for 3h.H 2 O( 10 mL) was added, and the organic layer was separated.…”

Section: Methodsmentioning

confidence: 99%

“…To find suitable organic materials, new monomeric and polymeric compounds have to be identified that show highly reversible redox chemistry . While the majority of organic electrode materials developed is of p type and can be reversibly oxidized at potentials of up to 4.1 V (vs. Li/Li + ), making them suitable as battery cathode materials, fewer examples of n‐type and potential anode materials exist . These, however, are necessary to build fully organic batteries.…”

Section: Introductionmentioning

confidence: 99%

“…[7] While the majority of organic electrode materials developed is of ptype and can be reversibly oxidized at potentials of up to 4.1 V( vs. Li/Li + ), [6,8] making them suitable as battery cathode materials, fewer examples of n-type and potential anode materials exist. [9,10] These,h owever,a re necessary to build fully organic batteries. Cyclooctatetraene (COT, 1)c ould be ideally suited as an n-type, redox-active unit.…”

Section: Introductionmentioning

confidence: 99%

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Evaluation of Cyclooctatetraene‐Based Aliphatic Polymers as Battery Materials: Synthesis, Electrochemical, and Thermal Characterization Supported by DFT Calculations

2017

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Organic electrode materials for rechargeable batteries are becoming a viable alternative for existing technologies. In particular, redox polymers have shown great performances. While many cathode‐active derivatives are known, the development of their anode‐active counterparts, required for the design of full‐organic batteries, lacks behind. Here we present investigation on the suitability of cyclooctatetraene (COT)‐based aliphatic polymers as anode‐active battery materials, inspired by the known reversible reduction chemistry of COT at low electrochemical potential. We found that both synthesized polystyrene derivatives, side‐group functionalized with COT, showed limited electrochemical reversibility of the reduction processes, whereas reductions proceeded reversibly in model compounds of these polymers. Differential scanning calorimetry measurements and density‐functional theory calculations showed that this incomplete reversibility was due to cross‐linking reactions occurring between COT units in the polymers. For the future of COT‐based redox polymers, we propose a molecular design that prevents these cross‐linking reactions.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Evaluation of Cyclooctatetraene‐Based Aliphatic Polymers as Battery Materials: Synthesis, Electrochemical, and Thermal Characterization Supported by DFT Calculations

2017

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“…Another possibility to increase the stability of redox functionalities is by incorporating them in a polymer. In this regard, polymers with pendant terephthalate groups have been synthesized and tested in lithium and sodium half‐cell experiments . Indeed, the stability of the resulting anodes is significantly improved compared to terephthalate small molecule‐based anodes.…”

Section: Electrodesmentioning

confidence: 99%

Sustainable Battery Materials from Biomass

Liedel

2020

ChemSusChem

127

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Sustainable sources of energy have been identified as a possible way out of today's oil dependency and are being rapidly developed. In contrast, storage of energy to a large extent still relies on heavy metals in batteries. Especially when built from biomass‐derived organics, organic batteries are promising alternatives and pave the way towards truly sustainable energy storage. First described in 2008, research on biomass‐derived electrodes has been taken up by a multitude of researchers worldwide. Nowadays, in principle, electrodes in batteries could be composed of all kinds of carbonized and noncarbonized biomass: On one hand, all kinds of (waste) biomass may be carbonized and used in anodes of lithium‐ or sodium‐ion batteries, cathodes in metal–sulfur or metal–oxygen batteries, or as conductive additives. On the other hand, a plethora of biomolecules, such as quinones, flavins, or carboxylates, contain redox‐active groups that can be used as redox‐active components in electrodes with very little chemical modification. Biomass‐based binders can replace toxic halogenated commercial binders to enable a truly sustainable future of energy storage devices. Besides the electrodes, electrolytes and separators may also be synthesized from biomass. In this Review, recent research progress in this rapidly emerging field is summarized with a focus on potentially fully biowaste‐derived batteries.

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“…[18][19][20][21] While reduction of CPDs led to a fairly stable radical anion species in absence of protons (Figure 1), electro-oxidation has been shown to yield in α-pyrones. [21,22] In the course of our efforts for the development of organic molecules acting as suitable energy storage materials, [23] we got interested in CPDs as a member of the carbonyl family, which recently turned to a promising class of energy storage compounds. [24][25][26] Herein, we present the synthesis of a series of tetraaryl cyclopentadienones aiming to readdress phenyl and heterocyclic substitution effects on both available electrochemical window as well as photophysical properties.…”

Section: Introductionmentioning

confidence: 99%

Tetraaryl Cyclopentadienones: Experimental and Theoretical Insights into Negative Solvatochromism and Electrochemistry

Meitinger¹,

Mengele²,

Witas³

et al. 2020

Eur J Org Chem

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The synthesis of a series of tetraaryl cyclopentadienones comprising different substitution patterns is reported. Their photophysical and electrochemical properties are investigated by UV/Vis spectroscopy and cyclic voltammetry as well as by supporting quantum chemical simulations and reveal a distinct effect of substituents on the redox behavior of the molecules as well as the absorption properties of this class of compounds. While electrochemical data display a shift in reduction potential of up to 200 mV between the differently substituted cyclopentadienones, their photophysical investigations in differently polar solvents suggest a negative solvatochromic effect, although protic solvents induce a bathochromic shift. Crystal structure analyses of some derivatives confirm similarity with related cyclopentadienones while providing insight into intermolecular C–H···O and C–H···π interactions in the solid state.

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Synthesis and solvent-free polymerisation of vinyl terephthalate for application as an anode material in organic batteries

Abstract: Solvent-free polymerisation of vinyl terephthalate was used to obtain high molecular weight polymers, whose corresponding Li-salts underlined the superiority of polymers regarding long term stability in battery tests compared to their monomeric counterparts.

Cited by 15 publications

References 32 publications

Evaluation of Cyclooctatetraene‐Based Aliphatic Polymers as Battery Materials: Synthesis, Electrochemical, and Thermal Characterization Supported by DFT Calculations

Evaluation of Cyclooctatetraene‐Based Aliphatic Polymers as Battery Materials: Synthesis, Electrochemical, and Thermal Characterization Supported by DFT Calculations

Sustainable Battery Materials from Biomass

Tetraaryl Cyclopentadienones: Experimental and Theoretical Insights into Negative Solvatochromism and Electrochemistry

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