Synthesis and charge/discharge properties of cellulose derivatives carrying free radicals

Qu, Jinqing; Khan, Fareha Zafar; Satoh, Masaharu; Wada, Jun; Hayashi, Hiroyuki; Mizoguchi, K.; Masuda, Toshio

doi:10.1016/j.polymer.2008.01.065

Cited by 44 publications

(26 citation statements)

References 41 publications

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“…The polymer should also have affinity for the electrolyte to support the ionic conductivity. To date, various backbone polymers, such as polymethacrylate, 8,9 poly(vinyl ether), 12 polystyrene, 16,17 polyether, 13 polynorbornene, 1820 polysiloxane, 21 polyacetylene, 22,23 cellulose, 24 and DNA complexes 25 have been reported. The polymer used must be dense in a thick electrode to obtain sufficient capacity.…”

Section: ç 2 Radical Polymers For Rechargeable Battery Electrodementioning

confidence: 99%

Organic Radical Battery Approaching Practical Use

Nakahara¹,

Oyaizu²,

Nishide³

2011

Chemistry Letters

271

221

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The electrochemical redox reactions of organic polymers bearing robust unpaired electrons were investigated to determine the applicability of these polymers to rechargeable batteries. Such an "organic radical battery" would be environmentally friendly and have high-power characteristics. This highlight review describes the performance of a battery using a nitroxyl radical polymer as the cathode active material. The electrontransfer mechanism and recent developments that should lead to the practical application of the organic radical battery are also described. Ç 1. IntroductionLithium-ion batteries are widely used power sources for portable electric devices such as cellular phones and laptop computers because of their high-energy density and long life. Application of these batteries is expanding to electric vehicles and domestic energy storage. 15 In these batteries, a lithium transition-metal oxide cathode and a graphite anode are used as energy storage electrodes. Since the lithium transition-metal oxide cathode comprises the main part of a lithium ion battery, the lithium transition-metal oxide mainly determines the battery's energy density and capacity. The lithium transition-metal oxide is charged/discharged electrochemically in accordance with deintercalation/intercalation of the lithium ions and oxidation/ reduction of the transition-metal ions. Although toxicity, safety, and resource availability are known problems with lithium transition-metal oxide, alternatives have been hardly reported except for conducting polymers and disulfide compounds. 6,7 Radical polymers are candidates for replacing lithium transition-metal oxide. 811 We call a polymer which has unpaired electrons a radical polymer. The disappearance of the unpaired electrons due to chemical bond formation can be suppressed by a precisely designed chemical structure through a combination of the resonance effect of the electrons and the sterically hindered effect of the substituent groups. Chemical groups such as nitroxyl, phenoxyl, and hydrazyl are robust structures with lessreactive unpaired electrons in the uncharged state. Radical polymers with alicyclic nitroxyl such as 2,2,6,6-tetramethylpiperidine-1-oxyl (TEMPO) and 2,2,5,5-tetramethylpyrrolidine-1-oxyl (PROXYL) in particular have been studied in detail.

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Section: ç 2 Radical Polymers For Rechargeable Battery Electrodementioning

confidence: 99%

Organic Radical Battery Approaching Practical Use

Nakahara¹,

Oyaizu²,

Nishide³

2011

Chemistry Letters

271

221

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“…[7] Recently, we have reported the synthesis of ethyl cellulose derivatives and cellulose acetate derivatives carrying TEMPO or PROXY radicals (TEMPO ¼ 2,2,6,6-tetramethyl-1-piperidinyloxy, PROXY ¼ 2,2,5,5-tetramethyl-1-pyrrolidinyloxy), and found that the free radical-containing cellulose derivatives demonstrate reversible charge/discharge processes. [8] In the present study, we disclose the synthesis of ethyl cellulose derivatives [poly (1)] carrying triphenylamine moieties by the reaction of 4-(diphenylamino)benzoic acid with the residual hydroxy groups of organosoluble cellulosics (Scheme 1), and clarify the fundamental properties and electro-optical characteristics of the formed polymer.…”

Section: Introductionmentioning

confidence: 95%

“…The degree of substitution with TPA groups in the cellulose derivatives was estimated by elemental analysis (%N content) of poly (1) according to Scheme 1. [8] The total degree of substitution (DS total ) of poly (1) was calculated by the following equation:…”

Section: Determination Of Degree Of Substitutionmentioning

confidence: 99%

Cellulose Derivatives Carrying Triphenylamine (TPA) Moieties: Synthesis and Electro‐Optical Properties

Liao

Huan-qin

et al. 2009

Macromolecular Bioscience

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A novel ethyl cellulose derivative [poly(1)] that carries triphenylamine moieties is synthesized with a moderate number-average molecular weight up to 78,200 in 85% yield by the reaction of 4-(diphenylamino)benzoic acid with the residual hydroxy group of ethyl cellulose. Poly(1) is soluble in common organic solvents including toluene, CHCl3, CH2Cl2, and tetrahydrofuran while insoluble in hexane, diethyl ether, and methanol. The polymer emits blue-green fluorescence with quantum yields up to 65% in CHCl3 and displays unique solvatochromism. The cyclic voltammograms of poly(1) indicate that the polymer carrying TPA moieties is electrochemically redox active. The onset temperature of weight loss of the poly(1) is about 177 degrees C according to thermogravimetric analysis in air.

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“…103 (60 f) ) 3.55 73 (20C) r = 1; [ 133 ] 113 (60 f) ) 3.55 85 (20C) r = 3; [ 133 ] 88 492.6 109 (2) 107 (80 f (1) 91 (80 f) ) 3.98 p) q) (150C) p-dope; (C 4 H 9 )N + as counter cation; [ 122 ] 82 (80 f) ) 2.65 p) q) (150C) n-dope; (C 4 H 9 )N + as counter cation; [ 122 ] 103 61 (80 f) ) 3.0 52 (110) 33 (60C) R = Ac, R' = TEMPO; [ 123 ] 104…”

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confidence: 99%

Organic Electrode Materials for Rechargeable Lithium Batteries

Liang

Tao

Chen

2012

Advanced Energy Materials

1,174

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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Synthesis and charge/discharge properties of cellulose derivatives carrying free radicals

Cited by 44 publications

References 41 publications

Organic Radical Battery Approaching Practical Use

Organic Radical Battery Approaching Practical Use

Cellulose Derivatives Carrying Triphenylamine (TPA) Moieties: Synthesis and Electro‐Optical Properties

Organic Electrode Materials for Rechargeable Lithium Batteries

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