Electroactive organics as promising anode materials for rechargeable lithium ion and sodium ion batteries

Xiang Li , Yan Wang , Linze Lv , Guobin Zhu , Qunting Qu , Honghe Zheng

Energy Materials ›› 2022, Vol. 2 ›› Issue (3) : 200014

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Energy Materials ›› 2022, Vol. 2 ›› Issue (3) :200014 DOI: 10.20517/energymater.2022.11
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Electroactive organics as promising anode materials for rechargeable lithium ion and sodium ion batteries

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Abstract

Electroactive organics have attracted significant attention as electrode materials for next-generation rechargeable batteries because of their structural diversity, molecular adjustability, abundance, flexibility, environmental friendliness and low cost. To date, a large number of organic materials have been applied in a variety of energy storage devices. However, the inherent problems of organic materials, such as their dissolution in electrolytes and low electronic conductivity, have restricted the development of organic electrodes. In order to solve these problems, many groups have carried out research and remarkable progress has been made. Nevertheless, most reviews of organic electrodes have focused on the positive electrode rather than the negative electrode. This review first provides an overview of the recent work on organic anodes for Li- and Na-ion batteries. Six categories of organic anodes are summarized and discussed. Many of the key factors that influence the electrochemical performance of organic anodes are highlighted and their prospects and remaining challenges are evaluated.

Keywords

Rechargeable batteries / organic anode materials / energy storage mechanism / structural regulation

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Xiang Li, Yan Wang, Linze Lv, Guobin Zhu, Qunting Qu, Honghe Zheng. Electroactive organics as promising anode materials for rechargeable lithium ion and sodium ion batteries. Energy Materials, 2022, 2(3): 200014 DOI:10.20517/energymater.2022.11

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References

[1]

Whittingham MS.Electrical energy storage and intercalation chemistry.Science1976;192:1126-7

[2]

Larcher D.Towards greener and more sustainable batteries for electrical energy storage.Nat Chem2015;7:19-29

[3]

Li M,Chen Z.30 years of lithium-ion batteries.Adv Mater2018;:e1800561

[4]

Yabuuchi N,Dahbi M.Research development on sodium-ion batteries.Chem Rev2014;114:11636-82

[5]

Amin K,Wei Z.Recent progress in polymeric carbonyl-based electrode materials for lithium and sodium ion batteries.Macromol Rapid Commun2019;40:e1800565

[6]

Slater MD,Lee E.Sodium-ion batteries.Adv Funct Mater2013;23:947-58

[7]

Lee S,Ku K.Recent progress in organic electrodes for Li and Na rechargeable batteries.Adv Mater2018;30:e1704682

[8]

Feng K,Liu W.Silicon-based anodes for lithium-ion batteries: from fundamentals to practical applications.Small2018;14:1702737

[9]

Shao Y,Li J,Huang X.Evaluation of the electrochemical and expansion performances of the Sn-Si/graphite composite electrode for the industrial use.Energy Mater 2022;2:200004

[10]

Chang H,Han X.Recent developments in advanced anode materials for lithium-ion batteries.Energy Mater 2021;1:100003

[11]

Huang Z,Qian K.Interfacial engineering enables Bi@C-TiO microspheres as superpower and long life anode for lithium-ion batteries.Nano Energy2018;51:137-45

[12]

Huang Z,Lu H.Grain-boundary-rich mesoporous NiTiO3 micro-prism as high tap-density, super rate and long life anode for sodium and lithium ion batteries.Energy Storage Materials2018;13:329-39

[13]

Lu Y.Prospects of organic electrode materials for practical lithium batteries.Nat Rev Chem2020;4:127-42

[14]

Shea JJ.Organic electrode materials for metal ion batteries.ACS Appl Mater Interfaces2020;12:5361-80

[15]

Huang T,Xiao JX,Wang G.Recent research on emerging organic electrode materials for energy storage.Energy Mater 2021;1:100009

[16]

Wang H,Nie H.Recent progress in carbonyl-based organic polymers as promising electrode materials for lithium-ion batteries (LIBs).J Mater Chem A2020;8:11906-22

[17]

An SY,Mcallister BT.Design strategies for organic carbonyl materials for energy storage: small molecules, oligomers, polymers and supramolecular structures.EcoMat2020;2

[18]

Peng H,Wang S.Molecular design strategies for electrochemical behavior of aromatic carbonyl compounds in organic and aqueous electrolytes.Adv Sci (Weinh)2019;6:1900431 PMCID:PMC6724361

[19]

Zhu L,Xie L.Conjugated carbonyl compounds as high-performance cathode materials for rechargeable batteries.Chem Mater2019;31:8582-612

[20]

Bhosale ME,Kim JM.Organic small molecules and polymers as an electrode material for rechargeable lithium ion batteries.J Mater Chem A2018;6:19885-911

[21]

Zhao Q,Lu Y,Liang J.Rechargeable lithium batteries with electrodes of small organic carbonyl salts and advanced electrolytes.Ind Eng Chem Res2016;55:5795-804

[22]

Muench S,Friebe C,Janoschka T.Polymer-based organic batteries.Chem Rev2016;116:9438-84

[23]

Tong Y,Zhang Y.Recent advances of covalent organic frameworks in lithium ion batteries.Inorg Chem Front2021;8:558-71

[24]

Liu X,Lai W.Porous organic polymers as promising electrode materials for energy storage devices.Adv Mater Technol

[25]

Zhao H,Wang L,He X.The opportunity of metal organic frameworks and covalent organic frameworks in lithium (ion) batteries and fuel cells.Energy Stor Mater2020;33:360-81

[26]

Kong L,Huang H,Bu X.Metal/covalent-organic framework based cathodes for metal-ion batteries.Adv Energy Mater2022;12:2100172

[27]

Song Z.Towards sustainable and versatile energy storage devices: an overview of organic electrode materials.Energy Environ Sci2013;6:2280

[28]

Schon TB,Li PF.The rise of organic electrode materials for energy storage.Chem Soc Rev2016;45:6345-404

[29]

Han X,Sun J.How many lithium ions can be inserted onto fused C6 aromatic ring systems?.Angew Chem Int Ed Engl2012;51:5147-51

[30]

Yang P,Bi S.Superior anodic lithium storage behavior of organic pigment 2,9-dimethylquinacridone.Chemical Engineering Journal2020;394:124924

[31]

Wang H,Si Z.Multi-ring aromatic carbonyl compounds enabling high capacity and stable performance of sodium-organic batteries.Energy Environ Sci2015;8:3160-5

[32]

Chen L,Zhao L.OH-substituted 2, 3-dichloro-5, 6-dicyano-1, 4-benzoquinone as highly stable organic electrode for lithium ion battery.Electrochimica Acta2017;258:677-83

[33]

Park J,Joo SH.Contorted polycyclic aromatic hydrocarbon: promising Li insertion organic anode.J Mater Chem A2018;6:12589-97

[34]

Park J,Park JH.Capacitive organic anode based on fluorinated-contorted hexabenzocoronene: applicable to lithium-ion and sodium-ion storage cells.Adv Sci (Weinh)2018;5:1801365 PMCID:PMC6299712

[35]

Wang C,Yao Z,Pei J.Using an organic acid as a universal anode for highly efficient Li-ion, Na-ion and K-ion batteries.Org Electro2018;62:536-41

[36]

Thangavel R,Ganesan BK,Yoon WS.Nanoengineered organic electrodes for highly durable and ultrafast cycling of organic sodium-ion batteries.Small2020;16:e2003688

[37]

Wang Y,Guo R.The effect of carboxyl group position of pyrazinedicarboxylic acid on electrochemical performances in lithium ion batteries anode.Journal of Power Sources2020;473:228515

[38]

Wang Y,Qu Q.Ultrahigh-capacity organic anode with high-rate capability and long cycle life for lithium-ion batteries.ACS Energy Lett2017;2:2140-8

[39]

Wang Y,Guo R.A high-capacity organic anode with self-assembled morphological transformation for green lithium-ion batteries.J Mater Chem A2019;7:22621-30

[40]

Guo R,Heng S,Battaglia VS.Pyromellitic dianhydride: a new organic anode of high electrochemical performances for lithium ion batteries.Journal of Power Sources2019;436:226848

[41]

Chen H,Hencz L.Exploring chemical, mechanical, and electrical functionalities of binders for advanced energy-storage devices.Chem Rev2018;118:8936-82

[42]

Fang C,Hubble D.Large-molecule decomposition products of electrolytes and additives revealed by on-electrode chromatography and MALDI.Joule2021;5:415-28

[43]

Taskin OS,Zhu T.Biomass-derived polymeric binders in silicon anodes for battery energy storage applications.Green Chem2021;23:7890-901

[44]

Ma C,Kang L.Non-conjugated dicarboxylate anode materials for electrochemical cells.Angew Chem Int Ed Engl2018;57:8865-70

[45]

Walker W,Vezin H.Electrochemical characterization of lithium 4,4′-tolane-dicarboxylate for use as a negative electrode in Li-ion batteries.J Mater Chem2011;21:1615-20

[46]

Renault S,Ebadi M,Brandell D.Dilithium 2-aminoterephthalate as a negative electrode material for lithium-ion batteries.Solid State Ionics2017;307:1-5

[47]

Fédèle L,Gottis S.2D-layered lithium carboxylate based on biphenyl core as negative electrode for organic lithium-ion batteries.Chem Mater2017;29:546-54

[48]

Renault S,Araujo CM,Edström K.Superlithiation of organic electrode materials: the case of dilithium benzenedipropiolate.Chem Mater2016;28:1920-6

[49]

Xu Y,Zhu C.High-performance of sodium carboxylate-derived materials for electrochemical energy storage.Sci China Mater2018;61:707-18

[50]

Cabañero JM Jr,Cannon KC,Armstrong AR.Sodium naphthalene-2,6-dicarboxylate: an anode for sodium batteries.ChemSusChem2019;12:4522-8

[51]

Gu T,Wang J.Electrochemical properties and kinetics of asymmetric sodium benzene-1,2,4-tricarboxylate as an anode material for sodium-organic batteries.ChemElectroChem2020;7:3517-21

[52]

Long R,Hu Z,Zhang L.Gradually activated lithium uptake in sodium citrate toward high-capacity organic anode for lithium-ion batteries.Rare Met2021;40:1366-72

[53]

Wang L,Qiu J,Xue J.Metal organic framework-derived cobalt dicarboxylate as a high-capacity anode material for lithium-ion batteries.Energy Technol2017;5:637-42

[54]

Wang L,Chen S.Zinc terephthalates ZnC8H4O4 as anodes for lithium ion batteries.Electrochimica Acta2017;235:304-10

[55]

Wang S,Zhang K,Tao Z.Organic Li4C8H2O6 nanosheets for lithium-ion batteries.Nano Lett2013;13:4404-9

[56]

Wan F,Guo J.Nanoeffects promote the electrochemical properties of organic Na2C8H4O4 as anode material for sodium-ion batteries.Nano Energy2015;13:450-7

[57]

Wang Y,Pan L.Understanding the size-dependent sodium storage properties of Na2C6O6-based organic electrodes for sodium-ion batteries.Nano Lett2016;16:3329-34

[58]

Choi A,Kim TK,Lee KT.4,4′-Biphenyldicarboxylate sodium coordination compounds as anodes for Na-ion batteries.J Mater Chem A2014;2:14986-93

[59]

Wang C,Fang Y.Extended π-conjugated system for fast-charge and -discharge sodium-ion batteries.J Am Chem Soc2015;137:3124-30

[60]

Abouimrane A,Eltayeb H.Sodium insertion in carboxylate based materials and their application in 3.6 V full sodium cells.Energy Environ Sci2012;5:9632

[61]

Zhao H,Zheng Y.Organic thiocarboxylate electrodes for a room-temperature sodium-ion battery delivering an ultrahigh capacity.Angew Chem Int Ed Engl2017;56:15334-8

[62]

Wang J,Xu L,He G.Three-electron redox enabled dithiocarboxylate electrode for superior lithium storage performance.ACS Appl Mater Interfaces2018;10:35469-76

[63]

Fédèle L,Bécuwe M.Hyper-conjugated lithium carboxylate based on a perylene unit for high-rate organic lithium-ion batteries.J Mater Chem A2014;2:18225-8

[64]

Zhang S,Han D,Wang S.Aqueous sodium alginate as binder: dramatically improving the performance of dilithium terephthalate-based organic lithium ion batteries.J Power Sources2019;438:227007

[65]

Zhao R,Ai X.Reversible Li and Na storage behaviors of perylenetetracarboxylates as organic anodes for Li- and Na-ion batteries.J Electroanal Chem2013;688:93-7

[66]

Veerababu M,Kothandaraman R.Improved electrochemical performance of lithium/sodium perylene-3,4,9,10-tetracarboxylate as an anode material for secondary rechargeable batteries.Int J Hydrog Energy2015;40:14925-31

[67]

Mihali VA,Nyholm L.Benzenediacrylates as organic battery electrode materials: Na versus Li.RSC Adv2014;4:38004-11

[68]

Medabalmi V,Ramani VK.Lithium salt of biphenyl tetracarboxylate as an anode material for Li/Na-ion batteries.Applied Surface Science2017;418:9-16

[69]

Wang S,Zhu Z,Zhao Q.All organic sodium-ion batteries with Na4C8H2O6.Angew Chem Int Ed Engl2014;53:5892-6

[70]

Hu P,Yang Y,Lin J.Renewable-biomolecule-based full lithium-ion batteries.Adv Mater2016;28:3486-92

[71]

Wu D,Du S.A low-cost non-conjugated dicarboxylate coupled with reduced graphene oxide for stable sodium-organic batteries.J Power Sources2018;398:99-105

[72]

Zhang H,Chen L,Hu H.Synthesis and electrochemical characterization of lithium carboxylate 2D compounds as high-performance anodes for Li-ion batteries.ChemElectroChem2019;7:306-13

[73]

Wu J,Wang C.Nanostructured conjugated ladder polymers for stable and fast lithium storage anodes with high-capacity.Adv Energy Mater2015;5:1402189

[74]

Wu J,Long G,Yan Q.Pushing up lithium storage through nanostructured polyazaacene analogues as anode.Angew Chem Int Ed Engl2015;54:7354-8

[75]

Xie J,Gu P.Novel conjugated ladder-structured oligomer anode with high lithium storage and long cycling capability.ACS Appl Mater Interfaces2016;8:16932-8

[76]

Yang L,Ma Y,Chang G.Intermolecular channel expansion induced by cation-π interactions to enhance lithium storage in a crosslinked π-conjugated organic anode.J Power Sources2020;449:227551

[77]

Xie J,Gu P,Xu ZJ.A novel quinone-based polymer electrode for high performance lithium-ion batteries.Sci China Mater2016;59:6-11

[78]

Wu D,Hu X.A sulfurization-based oligomeric sodium salt as a high-performance organic anode for sodium ion batteries.Chem Commun (Camb)2016;52:11207-10

[79]

Li K,Han D,Wang HG.Carbonyl-rich poly(pyrene-4,5,9,10-tetraone Sulfide) as anode materials for high-performance Li and Na-ion batteries.Chem Asian J2021;16:1973-8

[80]

Yamamoto R,Miyasaka M.Synthesis of conjugated carbonyl containing polymer negative electrodes for sodium ion batteries.J Electrochem Soc2018;165:A434-8

[81]

Wang Y,Liu H,Li B.A novel high-capacity anode material derived from aromatic imides for lithium-ion batteries.Small2018;14:e1704094

[82]

He J,Hu Q.Multi carbonyl polyimide as high capacity anode materials for lithium ion batteries.J Power Sources2020;451:227792

[83]

Zhang C,Mu P.Toward high performance thiophene-containing conjugated microporous polymer anodes for lithium-ion batteries through structure design.Adv Funct Mater2018;28:1705432

[84]

Castillo-Martínez E,Armand M.Polymeric Schiff bases as low-voltage redox centers for sodium-ion batteries.Angew Chem Int Ed Engl2014;53:5341-5

[85]

López-herraiz M,Carretero-gonzález J,Rojo T.Oligomeric-Schiff bases as negative electrodes for sodium ion batteries: unveiling the nature of their active redox centers.Energy Environ Sci2015;8:3233-41

[86]

Sun Y,Pan Q.A hyperbranched conjugated Schiff base polymer network: a potential negative electrode for flexible thin film batteries.Chem Commun (Camb)2016;52:3000-2

[87]

Ye H,Li H,Yin J.Facile synthesis of conjugated polymeric Schiff base as negative electrodes for lithium ion batteries.Electrochimica Acta2017;253:319-23

[88]

Sun T,Wang HG,Meng FL.A biodegradable polydopamine-derived electrode material for high-capacity and long-life lithium-ion and sodium-ion batteries.Angew Chem Int Ed Engl2016;55:10662-6

[89]

Zhang S,Hu P.Conjugated microporous polymers with excellent electrochemical performance for lithium and sodium storage.J Mater Chem A2015;3:1896-901

[90]

Deng W,Wu X.A low cost, all-organic Na-ion battery based on polymeric cathode and anode.Sci Rep2013;3:2671 PMCID:PMC3773616

[91]

Li G,Wang J.Electrochromic poly(chalcogenoviologen)s as anode materials for high-performance organic radical lithium-ion batteries.Angew Chem Int Ed Engl2019;58:8468-73

[92]

Kang H,Li C.Polyanthraquinone-triazine-a promising anode material for high-energy lithium-ion batteries.ACS Appl Mater Interfaces2018;10:37023-30

[93]

Lei Z,Xu Y.Boosting lithium storage in covalent organic framework via activation of 14-electron redox chemistry.Nat Commun2018;9:576 PMCID:PMC5805684

[94]

Lei Z,Sun W,Wang Y.Exfoliated triazine-based covalent organic nanosheets with multielectron redox for high-performance lithium organic batteries.Adv Energy Mater2019;9:1801010

[95]

Chen X,Wang L.High-lithium-affinity chemically exfoliated 2D covalent organic frameworks.Adv Mater2019;31:e1901640

[96]

Haldar S,Nandi S.High and reversible lithium ion storage in self-exfoliated triazole-triformyl phloroglucinol-based covalent organic nanosheets.Adv Energy Mater2018;8:1702170

[97]

Liu W,Bao Y.A two-dimensional conjugated aromatic polymer via C-C coupling reaction.Nat Chem2017;9:563-70

[98]

Lin Z,Zhang B.Solution-processed nitrogen-rich graphene-like holey conjugated polymer for efficient lithium ion storage.Nano Energy2017;41:117-27

[99]

Yang H,Han L.High conductive two-dimensional covalent organic framework for lithium storage with large capacity.ACS Appl Mater Interfaces2016;8:5366-75

[100]

Patra BC,Ghosh A.Covalent organic framework based microspheres as an anode material for rechargeable sodium batteries.J Mater Chem A2018;6:16655-63

[101]

Wang X,Xu Y.Conjugated microporous polytetra(2-Thienyl)ethylene as high performance anode material for lithium- and sodium-ion batteries.Macromol Chem Phys2018;219:1700524

[102]

Luo C,Xu Y.Graphene oxide wrapped croconic acid disodium salt for sodium ion battery electrodes.J Power Sources2014;250:372-8

[103]

Cao T,Zhang SW.A reduced graphene oxide/disodium terephthalate hybrid as a high-performance anode for sodium-ion batteries.Chemistry2017;23:16586-92

[104]

Dong C.Cobalt- and cadmium-based metal-organic frameworks as high-performance anodes for sodium ion batteries and lithium ion batteries.ACS Appl Mater Interfaces2017;9:7160-8

[105]

Mou C,Deng Q,Li J.Calcium terephthalate/graphite composites as anode materials for lithium-ion batteries.Ionics2015;21:1893-9

[106]

Zhao L,Hu Y.Disodium terephthalate (Na2C8H4O4) as high performance anode material for low-cost room-temperature sodium-ion battery.Adv Energy Mater2012;2:962-5

[107]

Wang Y,Qu Q,Battglia VS.A novel maleic acid/graphite composite anode for lithium ion batteries with high energy and power density.Carbon2018;132:420-9

[108]

Guo R,Shan X,Cao Z.A novel itaconic acid-graphite composite anode for enhanced lithium storage in lithium ion batteries.Carbon2019;152:671-9

[109]

Guo R,Wang Y,Lv L.A high-performance maleic acid/graphene/graphite composite anode under the effect of synergistic lithium storage mechanism.J Power Sources2020;479:229112

[110]

Ge D,Qu G.Nanostructured Co( ii )-based MOFs as promising anodes for advanced lithium storage.New J Chem2016;40:9238-44

[111]

Li T,Li J.Hericium erinaceus -like copper-based MOFs as anodes for high performance lithium ion batteries.ACS Appl Energy Mater2021;4:11400-7

[112]

Gou L,Lei H.Isostructural metal organic frameworks based on 1,4-naphthalene dicarboxylate as anodes for lithium ion battery.Materials Technology2017;32:630-7

[113]

Li C,Tong W.Ultrathin manganese-based metal-organic framework nanosheets: low-cost and energy-dense lithium storage anodes with the coexistence of metal and ligand redox activities.ACS Appl Mater Interfaces2017;9:29829-38

[114]

Yin C,Pan Y.Metal-organic framework as anode materials for lithium-ion batteries with high capacity and rate performance.ACS Appl Energy Mater2020;3:10776-86

[115]

Yang GP,Liu YF,Wu XL.[Co33-O)]-based metal-organic frameworks as advanced anode materials in K- and Na-ion batteries.ACS Appl Mater Interfaces2021;13:46902-8

[116]

Weng YG,Zhang ZR,Zhu QY.Tetrathiafulvalene-cobalt metal-organic frameworks for lithium-ion batteries with superb rate capability.Inorg Chem2021;60:17074-82

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