Synthesis and Properties of DNA Complexes Containing 2,2,6,6‐Tetramethyl‐1‐piperidinoxy (TEMPO) Moieties as Organic Radical Battery Materials

Qu, Jinqing; Morita, Ryuhei; Satoh, Masaharu; Wada, Jun; Terakura, Fumiaki; Mizoguchi, K.; Ogata, Naoya; Masuda, Toshio

doi:10.1002/chem.200800021

Cited by 54 publications

(27 citation statements)

References 38 publications

(68 reference statements)

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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

274

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

274

221

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“…13 C NMR (100 MHz, CDCl 3 ): d ¼ 24. 6, 28.1, 28.7, 29.0, 29.1, 29.2, 29.3, 30.2, 32.8, 34.0, 50.2, 61.7, 171.5, 173.3, 180.2. Compound 2 was synthesized as follows: The methyl groups of compound 1 were removed according to the literature method, [16] and then the product was reacted with 9H-carbazol-9-yl-ethanol referring to literature. [17] Yield 65%, white solid.…”

Section: Synthesis Of Lipidsmentioning

confidence: 99%

“…19,H 6.33,N 6.40. Found: C 67.16,H 6.54,N 6.10. Preparation of the DNA-Lipid Complex [14,16] A small amount of lipid (2.0 mmol) in THF was added slowly into double-distilled water to form a uniform solution. An aqueous solution (200 mL) of DNA-Na from salmon testes (0.50 g, 0.68 mmol bp À1 ) was added dropwise into an aqueous lipid solution (the feed mole ratio of phosphate to lipid was 1.50).…”

Section: Synthesis Of Lipidsmentioning

confidence: 99%

“…[14,15] Recently, we prepared DNA-cationic lipid complexes carrying 2,2,6,6-tetramethyl-1-piperidine-1-oxy (TEMPO), applied them as positive electrode materials of organic radical battery (ORB), and found that the complexes displayed a two-stage discharge process. [16] The total capacity of a TEMPO-containing DNA-cationic lipid complex reached 192% of its theoretical value for one electron redox reaction, suggesting two-electron redox reactions between the cation and the anion. We have also studied the DNA-lipid complexes carrying Cz and triphenylamine, and found that their solution emitted fluorescence in 5.7 and 76.4% quantum yields, respectively, and displayed electrochemical properties.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis and Electro‐Optical Properties of a Novel DNA–Lipid Complex Carrying Carbazole Moieties

Liu

Huan-qin

et al. 2010

Macro Chemistry & Physics

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A novel DNA–lipid complex carrying carbazole (Cz) moieties was prepared by substituting the sodium counter cation with cationic lipid, namely lipid(2Cz), in which the actual mole ratio of phosphate to lipid was 1:1.05. The DNA–lipid(2Cz) complex was soluble in common organic solvents including CHCl3, CH2Cl2, methanol, and ethanol, while insoluble in THF, toluene, and water. CD spectroscopy revealed that the DNA–lipid complex took a predominantly double helical structure in methanol and that the helical structure was fairly stable against heating. A solution of the DNA–lipid(2Cz) complex emitted fluorescence in 40.0% quantum yield, which was lower than that of the corresponding lipid(2Cz) (76%). The cyclic voltammograms of the complex indicated that the oxidation potential of DNA–lipid(2Cz) was 0.65 V. The onset temperature of weight loss of the DNA–lipid complex is 230 °C according to TGA in air.magnified image

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“…Although new kinds of organic radical polymer with the active centre attaching to different polymers [12] or the polymers substituted with different nitrox ides [13,14] have been synthesized, the delivered spe cific capacities of the materials do not exceed 150 mA h g -1 . For example, the theoretical specific capac ity of PTMA and PTVE is 111 [1] and 117 mA h g -1 [7], respectively.…”

Section: Introductionmentioning

confidence: 99%

Improvement of electrochemical properties of PTMA cathode by using carbon blacks with high specific surface area

et al. 2012

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Abstract-A PTMA (poly(4 methacryloyloxy 2,2,6,6 tetramethyl piperidine N oxyl)) electrode with high energy density is prepared with Black Pearl 2000 (BP 2000). For comparisons, vapor grown carbon fiber (VGCF) and acetylene black (AB) are also employed to fabricate the PTMA electrodes. The electrochemical properties of the electrode are improved obviously by employing BP 2000. The specific capacity of the PTMA BP electrode based on the mass of PTMA is 26.7% larger than that of the PTMA VGCF and PTMA AB electrodes at a 1 C rate. At higher discharge rates, the polarization degree of the Li/PTMA BP cell is the minimum one. At a discharge rate of 50 C, the specific capacity of the PTMA BP electrode is 104.9 mA h g -1 , and is 27.6 and 16.7% larger than that of the PTMA VGCF and PTMA AB electrodes, respectively. Besides, the discharge plateau of the Li/PTMA BP cell is 3.35 V, and is 0.03 and 0.13 V higher than that of the Li/PTMA AB and Li/PTMA VGCF cells, respectively. The larger specific capacity of BP 2000 and the improved electrochemical kinetics of PTMA at the surface of BP carbon, resulted from the larger surface area of BP 2000, are the main factors for improving the capacity and rate capability of the PTMA electrode. The high specific surface area of BP 2000 is also beneficial to the thorough contact of PTMA with BP carbon, result ing in the improved conductivity of the PTMA BP composites. The cycling performance of the PTMA BP electrode is also satisfied.

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Synthesis and Properties of DNA Complexes Containing 2,2,6,6‐Tetramethyl‐1‐piperidinoxy (TEMPO) Moieties as Organic Radical Battery Materials

Cited by 54 publications

References 38 publications

Organic Radical Battery Approaching Practical Use

Organic Radical Battery Approaching Practical Use

Synthesis and Electro‐Optical Properties of a Novel DNA–Lipid Complex Carrying Carbazole Moieties

Improvement of electrochemical properties of PTMA cathode by using carbon blacks with high specific surface area

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