电活性有机物在电极应用上的研究进展
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摘要
与无机电极材料相比,有机电极材料因为具有结构可设计、资源可再生以及成本低廉等特性,被视为具有前景的电化学储能材料。有机化合物电极材料主要包括含共轭羰基类化合物、含硫有机化合物以及氮氧自由基化合物等。本文主要概括了现阶段用以上三类化合物作为电极材料及其电化学性能所进行的探究,并进一步分析了这三类有机化合物应用在实际的储能电池中所需要的结构和性能上的改进,并进行了展望。
Studies of organic electrode materials have attracted enormous attentions in the field of battery electrode materials. Compared with their inorganic counterparts,organic electrode materials are more popular because their structures can be designed,their compositional materials are renewable,their production costs are low,and the organic compounds are environmentally friendly. In this review,recent progresses on the development of organic electrode materials are presented. These organic electrode materials include conjugated carbonyl compounds,sulphur compounds,and compounds with nitrogen oxygen free radicals,etc. Finally,our viewpoints and perspectives on the research of developing future organic electrode materials are discussed.
Studies of organic electrode materials have attracted enormous attentions in the field of battery electrode materials. Compared with their inorganic counterparts,organic electrode materials are more popular because their structures can be designed,their compositional materials are renewable,their production costs are low,and the organic compounds are environmentally friendly. In this review,recent progresses on the development of organic electrode materials are presented. These organic electrode materials include conjugated carbonyl compounds,sulphur compounds,and compounds with nitrogen oxygen free radicals,etc. Finally,our viewpoints and perspectives on the research of developing future organic electrode materials are discussed.
引文
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[11]张春明,黄昭,杨扬,等.聚吡咯/蒽醌-2-磺酸盐复合体系的制备及其在锂离子电池中的应用[J].有机化学,2014,37(7):1347-1351.
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[15]AI W,ZHOU W,DU Z,et al.Toward high energy organic cathodes for Li-ion batteries:a case study of vat dye/graphene composites[J].Adv Funct Mater,2016(5):1-9.
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[22]赖超,李国春,叶世海,等.高容量硫/碳复合正极材料[J].化学进展,2011,23(2):527-532.
[23]WANG J,CHEW S Y,ZHAO Z W,et al.Sulfur-mesoporous carbon composites in conjunction with a novel ionic liquid electrolyte for lithium rechargeable batteries[J].Carbon,2008,46(2):229-235.
[24]DING B,YUAN C,SHEN L,et al.Encapsulating sulfur into hierarchically ordered porous carbon as a high-performance cathode for lithium-sulfur batteries[J].Chem-A Eur J,2013,19(3):1013-1019.
[25]苑克国,王安邦,王维坤,等.正极材料单质硫在Li CF3SO3/DOL+DME电解液中的放电性能[J].电池,2007,37(3):168-170.
[26]肖立新,郭炳焜,李新海.聚合物锂离子电池[J].电池,2003,33(2):110-113.
[27]杨裕生,王维坤,苑克国,等.锂电池正极材料有机多硫化物的展望[J].电池,2002,6(32):1-5.
[28]张敬华,舒东,张永生,等.锂离子电池正极材料二巯基噻二唑的研究进展[J].电池,2005,35(3):237-239.
[29]ZHAN L,SONG Z,ZHANG J,et al.PEDOT:cathode active material with high specific capacity in novel electrolyte system[J].Electrochim Acta,2008,53(28):8319-8323.
[30]ZHAN L,SONG Z,SHAN N,et al.Poly(tetrahydrobenzodithiophene):high discharge specific capacity a cathode material for lithium batteries[J].J Power Sources,2009,193(2):859-863.
[31]DENG S R,KONG L B,HU G Q,et al.Benzene-based polyorganodisulfide cathode materials for secondary lithium batteries[J].Electrochim Acta,2006,51(13):2589-2593.
[32]杨小东,瞿金清.有机自由基电池[J].化学进展,2013,25(8):1283-1291.
[33]NAKAHARA K,IWASA S,IRIYAMA J,et al.Electrochemical and spectroscopic measurements for stable nitroxyl radicals[J].Electrochim Acta,2006,52(3):921-927.
[34]NAKAHARA K,IWASA S,SATOH M,et al.Rechargeable batteries with organic radical cathodes[J].Chem Phy Lett,2002,359(5):351-354.
[35]NAKAHARA K,IRIYAMA J,IWASA S,et al.Al-laminated film packaged organic radical battery for high-power applications[J].J Power Sources,2007,163(2):1110-1113.
[36]NAKAHARA K,IRIYAMA J,IWASA S,et al.Cell properties for modified PTMA cathodes of organic radical batteries[J].JPower Sources,2007,165(1):398-402.
[37]CHOI W,OHTANI S,OYAIZU K,et al.Radical polymer-wrapped SWNTs at a molecular level:high-rate redox mediation through a percolation network for a transparent charge-storage material[J].Adv Mater,2011,23(38):4440-4443.
[38]BUGNON L,MORTON C J H,NOVAK P,et al.Synthesis of poly(4-methacryloyloxy-TEMPO)via group-transfer polymerization and its evaluation in organic radical battery[J].Chem Mater,2007,19(11):2910-2914.
[39]SU C,JI L,XU L,et al.A polytriphenylamine derivative exhibiting a four-electron redox center as a high free radical density organic cathode[J].RSC Adv,2016,6(27):22989-22995.
[40]XU L,JI L,WANG G,et al.A novel nitroxide radical polymer-containing conductive polyaniline as molecular skeleton:its synthesis and electrochemical properties as organic cathode[J].Ionics,2016,22(8):1377-1385.
[41]POIZOT P,DOLHEM F.Clean energy new deal for a sustainable world:from non-CO2generating energy sources to greener electrochemical storage devices[J].Energ Environ Sci,2011,4(6):2003-2019.
[42]CASADO N,HERNANDEZ G,VELOSO A,et al.PEDOT radical polymer with synergetic redox and electrical properties[J].ACS Macro Lett,2015,5(1):59-64.
[43]SUGURO M,IWASA S,KUSACHI Y,et al.Cationic polymerization of poly(vinyl ether)bearing a TEMPO radical:a new cathode-active material for organic radical batteries[J].Macromol Rapid Commun,2007,28(18):1929-1933.
[44]SUGA T,PU Y J,OYAIZU K,et al.Electron-transfer kinetics of nitroxide radicals as an electrode-active material[J].Bull Chem Soc Jpn,2004,77(12):2203-2204.
[2]WILLIAMS D L,BYRNE J J,DRISCOLL J S.A high energy density lithium/dichloroisocyanuric acid battery system[J].JElectrochem Soc,1969,116(1):2-4.
[3]ALT H,BINDER H,KOHLING A,et al.Investigation into the use of quinone compounds for battery cathodes[J].Electrochim Acta,1972,17(5):873-887.
[4]徐国祥,其鲁,闻雷,等.聚1,5-二氨基蒽醌二次锂电池正极材料研究[J].高分子学报,2006(6):795-799.
[5]CHEN H Y,ARMAND M,COURTY M,et al.Lithium salt of tetrahydroxybenzoquinone:toward the development of a sustainable Li-ion batteries[J].J Am Chem Soc,2009,131(25):8984-8988.
[6]王维坤,张勇勇,王安邦,等.锂电池正极材料1,4,5,8-四羟基-9,10-蒽醌的电化学性能[J].Acta Phys-Chim Sin,2010,26(1):47-50.
[7]徐艳,文越华,程杰,等.酚醌类有机物电化学性能及化学电源上的应用[J].电源技术,2011,35(2):153-157.
[8]HAN X Y,QING G Y,SUN J T,et al.How many lithium ions can be inserted onto fused C6 aromatic ring systems?[J/OL].Angew Chem Int Ed,2012,51:5147-5151.http://dx.doi.org/10.1002/anie.201109187.
[9]王诗文.A-4C-8H-2O-6(A=Li/Na)与联苯醌类羰基化合物的制备及锂/钠离子电池性能研究[D].天津:南开大学,2014.
[10]吴海平,王凯,孟月娜,等.基于聚酰亚胺类复合材料的有机正极材料[C]//成都:中国化学会第28届学术年会第10分会场摘要集,2012:1.
[11]张春明,黄昭,杨扬,等.聚吡咯/蒽醌-2-磺酸盐复合体系的制备及其在锂离子电池中的应用[J].有机化学,2014,37(7):1347-1351.
[12]XU F,WANG H,LIN J,et al.Poly(anthraquinonyl imide)as a high capacity organic cathode material for Na-ion batteries[J].J Mate Chem A,2016,4(29):11491-11497.
[13]周晓,孙敏强,王庚超.石墨烯负载新型π-共轭聚合物纳米复合电极材料的合成及其超级电容特性[J].物理化学学报,2016,32(4):975-982.
[14]NOKAMI T,MATSUO T,INATOMI Y,et al.Polymer-bound pyrene-4,5,9,10-tetraone for fast-charge and-discharge lithium-ion batteries with high capacity[J].J Am Chem Soc,2012,134(48):19694-19700.
[15]AI W,ZHOU W,DU Z,et al.Toward high energy organic cathodes for Li-ion batteries:a case study of vat dye/graphene composites[J].Adv Funct Mater,2016(5):1-9.
[16]WANG Y,DING Y,PAN L,et al.Understanding the size-dependent sodium storage properties of Na2C6O6-based organic electrodes for sodium-ion batteries[J].Nano Lett,2016,16(5):3329-3334.
[17]REDDY A L M,NAGARAJAN S,CHUMYIM P,et al.Lithium storage mechanisms in purpurin based organic lithium ion battery electrodes[J].Sci Rep,2012,2(960):1-5.
[18]RENAULT S,BRANDELL D,GUSTAFSSON T,et al.Improving the electrochemical performance of organic Li-ion battery electrodes[J].Chem Commun,2013,49(19):1945-1947.
[19]MARMORSTEIN D,YU T H,STRIEBEM K A,et al.Electrochemical performance of lithium/sulfur cells with three different polymer electrolytes[J].J Power Sources,2000,89(1):219-226.
[20]MIKHAYLIK Y V,AKRIDGE J R.Polysulfide shuttle study in the Li/S battery system[J].J Electrochem Soc,2004,151(11):A1969-A1976.
[21]李琰,马志远,邢晨曦.锂电池正极材料多硫化碳炔的制备及性能研究[J].上海化工,2009(7):10-12.
[22]赖超,李国春,叶世海,等.高容量硫/碳复合正极材料[J].化学进展,2011,23(2):527-532.
[23]WANG J,CHEW S Y,ZHAO Z W,et al.Sulfur-mesoporous carbon composites in conjunction with a novel ionic liquid electrolyte for lithium rechargeable batteries[J].Carbon,2008,46(2):229-235.
[24]DING B,YUAN C,SHEN L,et al.Encapsulating sulfur into hierarchically ordered porous carbon as a high-performance cathode for lithium-sulfur batteries[J].Chem-A Eur J,2013,19(3):1013-1019.
[25]苑克国,王安邦,王维坤,等.正极材料单质硫在Li CF3SO3/DOL+DME电解液中的放电性能[J].电池,2007,37(3):168-170.
[26]肖立新,郭炳焜,李新海.聚合物锂离子电池[J].电池,2003,33(2):110-113.
[27]杨裕生,王维坤,苑克国,等.锂电池正极材料有机多硫化物的展望[J].电池,2002,6(32):1-5.
[28]张敬华,舒东,张永生,等.锂离子电池正极材料二巯基噻二唑的研究进展[J].电池,2005,35(3):237-239.
[29]ZHAN L,SONG Z,ZHANG J,et al.PEDOT:cathode active material with high specific capacity in novel electrolyte system[J].Electrochim Acta,2008,53(28):8319-8323.
[30]ZHAN L,SONG Z,SHAN N,et al.Poly(tetrahydrobenzodithiophene):high discharge specific capacity a cathode material for lithium batteries[J].J Power Sources,2009,193(2):859-863.
[31]DENG S R,KONG L B,HU G Q,et al.Benzene-based polyorganodisulfide cathode materials for secondary lithium batteries[J].Electrochim Acta,2006,51(13):2589-2593.
[32]杨小东,瞿金清.有机自由基电池[J].化学进展,2013,25(8):1283-1291.
[33]NAKAHARA K,IWASA S,IRIYAMA J,et al.Electrochemical and spectroscopic measurements for stable nitroxyl radicals[J].Electrochim Acta,2006,52(3):921-927.
[34]NAKAHARA K,IWASA S,SATOH M,et al.Rechargeable batteries with organic radical cathodes[J].Chem Phy Lett,2002,359(5):351-354.
[35]NAKAHARA K,IRIYAMA J,IWASA S,et al.Al-laminated film packaged organic radical battery for high-power applications[J].J Power Sources,2007,163(2):1110-1113.
[36]NAKAHARA K,IRIYAMA J,IWASA S,et al.Cell properties for modified PTMA cathodes of organic radical batteries[J].JPower Sources,2007,165(1):398-402.
[37]CHOI W,OHTANI S,OYAIZU K,et al.Radical polymer-wrapped SWNTs at a molecular level:high-rate redox mediation through a percolation network for a transparent charge-storage material[J].Adv Mater,2011,23(38):4440-4443.
[38]BUGNON L,MORTON C J H,NOVAK P,et al.Synthesis of poly(4-methacryloyloxy-TEMPO)via group-transfer polymerization and its evaluation in organic radical battery[J].Chem Mater,2007,19(11):2910-2914.
[39]SU C,JI L,XU L,et al.A polytriphenylamine derivative exhibiting a four-electron redox center as a high free radical density organic cathode[J].RSC Adv,2016,6(27):22989-22995.
[40]XU L,JI L,WANG G,et al.A novel nitroxide radical polymer-containing conductive polyaniline as molecular skeleton:its synthesis and electrochemical properties as organic cathode[J].Ionics,2016,22(8):1377-1385.
[41]POIZOT P,DOLHEM F.Clean energy new deal for a sustainable world:from non-CO2generating energy sources to greener electrochemical storage devices[J].Energ Environ Sci,2011,4(6):2003-2019.
[42]CASADO N,HERNANDEZ G,VELOSO A,et al.PEDOT radical polymer with synergetic redox and electrical properties[J].ACS Macro Lett,2015,5(1):59-64.
[43]SUGURO M,IWASA S,KUSACHI Y,et al.Cationic polymerization of poly(vinyl ether)bearing a TEMPO radical:a new cathode-active material for organic radical batteries[J].Macromol Rapid Commun,2007,28(18):1929-1933.
[44]SUGA T,PU Y J,OYAIZU K,et al.Electron-transfer kinetics of nitroxide radicals as an electrode-active material[J].Bull Chem Soc Jpn,2004,77(12):2203-2204.
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