Covalent Organic Framework-Based Electrolytes for Lithium Solid-State Batteries—Recent Progress
Abstract
:1. Introduction
2. COF Solid-State Electrolytes
2.1. C-N Linkage
2.1.1. Imine Bond
2.1.2. Imide Bond
2.1.3. β-Ketoenamine Bond
2.1.4. Squaraine Linkage
2.1.5. Triazine Linkage
2.2. C-B and O-B Linkages
2.2.1. Spiroborate Bond
2.2.2. Boronate Ester
3. Conclusions, Challenges, and Future Directions
- −
- Building blocks and pore structure Investigating the type of building blocks used and understanding the impact on the 2D or 3D pore structures of COFs is crucial for optimizing charge mobility within the material.
- −
- Structure stiffness Balancing the degree of structure stiffness is important, as more rigid structures can impede ion mobility, while excessively flexible structures can compromise mechanical integrity.
- −
- Ionic character Exploring the presence of active centers (anionic, cationic, mixed, or neutral) within COFs can aid in the dissolving of lithium salts, which are important for ion conduction.
- −
- Li donor The selection of suitable lithium salts, such as LiPF6, LiClO4, LiTSFI, is crucial for facilitating ion transport within the COF structure.
- −
- Plasticizers and fillers Understanding the influence of plasticizers and fillers on Li+ mobility is important. Ideally, COF materials should possess intrinsic conductivity without the need for additional plasticizers.
- −
- Solvents Delving into the role of solvents in the dissociation of lithium donors can provide insights into improving ion conductivity within COF electrolytes.
Type of Bond | Linkers | σLi+ | Li+ Transference Number; Stability vs. Li+|Li | Ref. |
---|---|---|---|---|
Squaraine | -Squaric acid -Melamine | 8.2 × 10−6 S/cm @30 °C | 0.62; - | [53] |
Triazine | -Triazine -Piperazine | 1.49 × 10−3 S/cm @RT | 0.84; - | [54] |
Imine | -Trisfromylbenzene -Fluorinated-imidazole containing diamine (see Figure 1) | 7.2 × 10−3 S/cm @RT | 0.81; 0–4.5 V | [39] |
Imine | -Trisfromylbenzene -Diaminobenzene | - | 0.85; Stable near 0 V | [38] |
Imine | -2,4,6-Tris(4-aminophenyl)-1,3,5-triazine -2,3,5,6-Tetrafluoroterephthaldehyde | 5.3 × 10−3 S/cm @30 °C | -; up to 5.6 V | [40] |
Imine | -Tri(4-aminophenyl)benzene -Dimethoxyterephthalaldehyde | 2.8 × 10−4 S/cm @30 °C | - | [41] |
Imine | -3,5-Bis(5-formylthiophen-2-yl)phenyl]thiophene-2-carbaldehyde -Tri(4-aminophenyl)amine | 2.2 × 10−4 S/cm @40 °C | -; up to 3.4 V | [42] |
Imine | -2,5-Dihydroxybenzaldehyde -Tri(4-aminophenyl)benzene | 9.74 × 10−5 S/cm @30°C | -; up to 5.5 V | [43] |
Imide | -2,4,6-Tris(2-aminophenol)-triazine -Pyromellitic dianhydride | 1.36 × 10−5 S/cm @30 °C | 0.95; up to 5.5 V | [46] |
β-Ketoenamine | -Triformylphloroglucinol -Benzidine | 2.14 × 10−4 S∙cm−1 @25 °C | 0.724; - | [50] |
β-Ketoenamine | -1,4-Phenylenediamine-2-sulfonic acid -Triformylphloroglucinol | 2.7 × 10−7 S∙cm−1 @RT | 0.9; - | [49] |
Boronate ester | -Benzene dibornic acid -Hexahydroxytriphenylene | 2.6 × 10−4 S∙cm−1 @25 °C | -; −1–10 V | [56] |
Spiroborate | -Trimethyl borate -3,6-Di(prop-1-yn-1-yl)-9H-fluorene-9,9-dicarboxylate | 3.05 × 10−5 S/cm @RT | 0.8; - | [55] |
Spiroborate | -Trimethyl borate -γ-Cyclodextrin | 2.7 × 10−3 S/cm @RT | - | [27] |
Author Contributions
Funding
Data Availability Statement
Conflicts of Interest
References
- Koohi-Fayegh, S.; Rosen, M. A review of energy storage types, applications and recent developments. J. Energy Storage 2020, 27, 101047. [Google Scholar] [CrossRef]
- Xiao, J.; Li, H.; Zhang, H.; He, S.; Zhang, Q.; Liu, K.; Jiang, S.; Duan, G.; Zhang, K. Nanocellulose and its derived composite electrodes toward supercapacitors: Fabrication, properties, and challenges. J. Bioresour. Bioprod. 2022, 7, 245–269. [Google Scholar] [CrossRef]
- Hassan, Q.; Sameen, A.Z.; Salman, H.M.; Jaszczur, M.; Al-Jiboory, A.K. Hydrogen energy future: Advancements in storage technologies and implications for sustainability. J. Energy Storage 2023, 72, 108404. [Google Scholar] [CrossRef]
- Masias, A.; Marcicki, J.; Paxton, W.A. Opportunities and Challenges of Lithium Ion Batteries in Automotive Applications. ACS Energy Lett. 2021, 6, 621–630. [Google Scholar] [CrossRef]
- Nzereogu, P.; Omah, A.; Ezema, F.; Iwuoha, E.; Nwanya, A. Anode materials for lithium-ion batteries: A review. Appl. Surf. Sci. Adv. 2022, 9, 100233. [Google Scholar] [CrossRef]
- Li, D.; Guo, H.; Jiang, S.; Zeng, G.; Zhou, W.; Li, Z. Microstructures and electrochemical performances of TiO2-coated Mg–Zr co-doped NCM as a cathode material for lithium-ion batteries with high power and long circular life. New J. Chem. 2021, 45, 19446–19455. [Google Scholar] [CrossRef]
- Jayalakshmi, T.; Harini, R.; Nagaraju, G. Lithium ion battery performance of micro and nano-size V2O5 cathode materials. Mater. Today Proc. 2022, 65, 200–206. [Google Scholar] [CrossRef]
- Blomgren, G.E. The Development and Future of Lithium Ion Batteries. J. Electrochem. Soc. 2017, 164, A5019–A5025. [Google Scholar] [CrossRef]
- Kim, T.; Song, W.; Son, D.-Y.; Ono, L.K.; Qi, Y. Lithium-ion batteries: Outlook on present, future, and hybridized technologies. J. Mater. Chem. A 2019, 7, 2942–2964. [Google Scholar] [CrossRef]
- Tian, Y.; Zeng, G.; Rutt, A.; Shi, T.; Kim, H.; Wang, J.; Koettgen, J.; Sun, Y.; Ouyang, B.; Chen, T.; et al. Promises and Challenges of Next-Generation “Beyond Li-ion” Batteries for Electric Vehicles and Grid Decarbonization. Chem. Rev. 2021, 121, 1623–1669. [Google Scholar] [CrossRef]
- Janek, J.; Zeier, W.G. A solid future for battery development. Nat. Energy 2016, 1, 16141. [Google Scholar] [CrossRef]
- Deng, W.; Xu, Y.; Zhang, X.; Li, C.; Liu, Y.; Xiang, K.; Chen, H. (NH4)2Co2V10O28·16H2O/(NH4)2V10O25·8H2O heterostructure as cathode for high-performance aqueous Zn-ion batteries. J. Alloys Compd. 2022, 903, 163824. [Google Scholar] [CrossRef]
- Zhou, G.; Chen, H.; Cui, Y. Formulating energy density for designing practical lithium–sulfur batteries. Nat. Energy 2022, 7, 312–319. [Google Scholar] [CrossRef]
- Yang, Y.; Hong, X.-J.; Song, C.-L.; Li, G.-H.; Zheng, Y.-X.; Zhou, D.-D.; Zhang, M.; Cai, Y.-P.; Wang, H. Lithium bis(trifluoromethanesulfonyl)imide assisted dual-functional separator coating materials based on covalent organic frameworks for high-performance lithium–selenium sulfide batteries. J. Mater. Chem. A 2019, 7, 16323–16329. [Google Scholar] [CrossRef]
- Deng, W.-N.; Li, Y.-H.; Xu, D.-F.; Zhou, W.; Xiang, K.-X.; Chen, H. Three-dimensional hierarchically porous nitrogen-doped carbon from water hyacinth as selenium host for high-performance lithium–selenium batteries. Rare Met. 2022, 41, 3432–3445. [Google Scholar] [CrossRef]
- Tian, H.; Tian, H.; Wang, S.; Chen, S.; Zhang, F.; Song, L.; Liu, H.; Liu, J.; Wang, G. High-power lithium–selenium batteries enabled by atomic cobalt electrocatalyst in hollow carbon cathode. Nat. Commun. 2020, 11, 5025. [Google Scholar] [CrossRef] [PubMed]
- McDonagh, A.M.; Tkacheva, A.; Sun, B.; Zhang, J.; Wang, G. Nitronyl nitroxide-based redox mediators for Li-O2 batteries. J. Phys. Chem. C 2021, 125, 2824–2830. [Google Scholar] [CrossRef]
- Kamaya, N.; Homma, K.; Yamakawa, Y.; Hirayama, M.; Kanno, R.; Yonemura, M.; Kamiyama, T.; Kato, Y.; Hama, S.; Kawamoto, K.; et al. A lithium superionic conductor. Nat. Mater. 2011, 10, 682–686. [Google Scholar] [CrossRef] [PubMed]
- Hayamizu, K.; Seki, S.; Haishi, T. 7Li NMR diffusion studies in micrometre-space for perovskite-type Li0.33La0.55TiO3 (LLTO) influenced by grain boundaries. Solid State Ion. 2018, 326, 37–47. [Google Scholar] [CrossRef]
- Polczyk, T.; Zając, W.; Ziąbka, M.; Świerczek, K. Mitigation of grain boundary resistance in La2/3-xLi3xTiO3 perovskite as an electrolyte for solid-state Li-ion batteries. J. Mater. Sci. 2020, 56, 2435–2450. [Google Scholar] [CrossRef]
- Wu, J.-F.; Guo, X. Size effect in nanocrystalline lithium-ion conducting perovskite: Li0.30La0.57TiO3. Solid State Ion. 2017, 310, 38–43. [Google Scholar] [CrossRef]
- Xu, S.; Hu, L. Towards a high-performance garnet-based solid-state Li metal battery: A perspective on recent advances. J. Power Sources 2020, 472, 228571. [Google Scholar] [CrossRef]
- Zhou, D.; Shanmukaraj, D.; Tkacheva, A.; Armand, M.; Wang, G. Polymer Electrolytes for Lithium-Based Batteries: Advances and Prospects. Chem 2019, 5, 2326–2352. [Google Scholar] [CrossRef]
- Li, C.; Liu, L.; Kang, J.; Xiao, Y.; Feng, Y.; Cao, F.-F.; Zhang, H. Pristine MOF and COF materials for advanced batteries. Energy Storage Mater. 2020, 31, 115–134. [Google Scholar] [CrossRef]
- Jiang, S.; Lv, T.; Peng, Y.; Pang, H. MOFs Containing Solid-State Electrolytes for Batteries. Adv. Sci. 2023, 10, 2206887. [Google Scholar] [CrossRef]
- Wei, T.; Wang, Z.-M.; Zhang, Q.; Zhou, Y.; Sun, C.; Wang, M.; Liu, Y.; Wang, S.; Yu, Z.; Qiu, X.-Y.; et al. Metal–organic framework-based solid-state electrolytes for all solid-state lithium metal batteries: A review. CrystEngComm 2022, 24, 5014–5030. [Google Scholar] [CrossRef]
- Zhang, Y.; Duan, J.; Ma, D.; Li, P.; Li, S.; Li, H.; Zhou, J.; Ma, X.; Feng, X.; Wang, B. Three-Dimensional Anionic Cyclodextrin-Based Covalent Organic Frameworks. Angew. Chem. Int. Ed. 2017, 56, 16313–16317. [Google Scholar] [CrossRef]
- Nagai, A.; Guo, Z.; Feng, X.; Jin, S.; Chen, X.; Ding, X.; Jiang, D. Pore surface engineering in covalent organic frameworks. Nat. Commun. 2011, 2, 536. [Google Scholar] [CrossRef] [PubMed]
- Fang, Q.; Zhuang, Z.; Gu, S.; Kaspar, R.B.; Zheng, J.; Wang, J.; Qiu, S.; Yan, Y. Designed synthesis of large-pore crystalline polyimide covalent organic frameworks. Nat. Commun. 2014, 5, 4503. [Google Scholar] [CrossRef] [PubMed]
- Geng, K.; He, T.; Liu, R.; Dalapati, S.; Tan, K.T.; Li, Z.; Tao, S.; Gong, Y.; Jiang, Q.; Jiang, D. Covalent Organic Frameworks: Design, Synthesis, and Functions. Chem. Rev. 2020, 120, 8814–8933. [Google Scholar] [CrossRef] [PubMed]
- Ibrahim, M.; Abdelhamid, H.N.; Abuelftooh, A.M.; Mohamed, S.G.; Wen, Z.; Sun, X. Covalent organic frameworks (COFs)-derived nitrogen-doped carbon/reduced graphene oxide nanocomposite as electrodes materials for supercapacitors. J. Energy Storage 2022, 55, 105375. [Google Scholar] [CrossRef]
- Dai, Y.; Wang, Y.; Li, X.; Cui, M.; Gao, Y.; Xu, H.; Xu, X. In situ form core-shell carbon nanotube-imide COF composite for high performance negative electrode of pseudocapacitor. Electrochim. Acta 2022, 421, 140470. [Google Scholar] [CrossRef]
- Nagai, A. Covalent Organic Frameworks, 1st ed.; Jenny Stanford Publishing Pte. Ltd.: Singapore, 2020; Volume 1. [Google Scholar]
- Gu, S.; Chen, J.; Hao, R.; Chen, X.; Wang, Z.; Hussain, I.; Liu, G.; Liu, K.; Gan, Q.; Li, Z.; et al. Redox of anionic and cationic radical intermediates in a bipolar polyimide COF for high-performance dual-ion organic batteries. Chem. Eng. J. 2023, 454, 139877. [Google Scholar] [CrossRef]
- Cai, Y.-Q.; Gong, Z.-T.; Rong, Q.; Liu, J.-M.; Yao, L.-F.; Cheng, F.-X.; Liu, J.-J.; Xia, S.-B.; Guo, H. Improved and stable triazine-based covalent organic framework for lithium storage. Appl. Surf. Sci. 2022, 594, 153481. [Google Scholar] [CrossRef]
- Wu, M.; Zhou, Z. Covalent organic frameworks as electrode materials for rechargeable metal-ion batteries. Interdiscip. Mater. 2023, 2, 231–259. [Google Scholar] [CrossRef]
- Zeng, S.-M.; Huang, X.-X.; Ma, Y.-J.; Zhi, L.-J. A review of covalent organic framework electrode materials for rechargeable metal-ion batteries. New Carbon Mater. 2021, 36, 1–18. [Google Scholar] [CrossRef]
- Xu, Y.; Zhou, Y.; Li, T.; Jiang, S.; Qian, X.; Yue, Q.; Kang, Y. Multifunctional covalent organic frameworks for high capacity and dendrite-free lithium metal batteries. Energy Storage Mater. 2020, 25, 334–341. [Google Scholar] [CrossRef]
- Hu, Y.; Dunlap, N.; Wan, S.; Lu, S.; Huang, S.; Sellinger, I.; Ortiz, M.; Jin, Y.; Lee, S.-H.; Zhang, W. Crystalline Lithium Imidazolate Covalent Organic Frameworks with High Li-Ion Conductivity. J. Am. Chem. Soc. 2019, 141, 7518–7525. [Google Scholar] [CrossRef] [PubMed]
- Niu, C.; Luo, W.; Dai, C.; Yu, C.; Xu, Y. High-Voltage-Tolerant Covalent Organic Framework Electrolyte with Holistically Oriented Channels for Solid-State Lithium Metal Batteries with Nickel-Rich Cathodes. Angew. Chem. Int. Ed. 2021, 60, 24915–24923. [Google Scholar] [CrossRef]
- Wang, Z.; Zheng, W.; Sun, W.; Zhao, L.; Yuan, W. Covalent Organic Frameworks-Enhanced Ionic Conductivity of Polymeric Ionic Liquid-Based Ionic Gel Electrolyte for Lithium Metal Battery. ACS Appl. Energy Mater. 2021, 4, 2808–2819. [Google Scholar] [CrossRef]
- Shan, Z.; Wu, M.; Du, Y.; Xu, B.; He, B.; Wu, X.; Zhang, G. Covalent organic framework-based electrolytes for fast Li+conduction and high-temperature solid-state lithium-ion batteries. Chem. Mater. 2021, 33, 5058–5066. [Google Scholar] [CrossRef]
- Li, Z.; Liu, Z.; Li, Z.; Wang, T.; Zhao, F.; Ding, X.; Feng, W.; Han, B. Defective 2D Covalent Organic Frameworks for Postfunctionalization. Adv. Funct. Mater. 2020, 30, 1909267. [Google Scholar] [CrossRef]
- Steinstraeter, M.; Heinrich, T.; Lienkamp, M. Effect of Low Temperature on Electric Vehicle Range. World Electr. Veh. J. 2021, 12, 115. [Google Scholar] [CrossRef]
- Xuan, Y.; Wang, Y.; He, B.; Bian, S.; Liu, J.; Xu, B.; Zhang, G. Covalent Organic Framework-Derived Quasi-Solid Electrolyte for Low-Temperature Lithium-Ion Battery. Chem. Mater. 2022, 34, 9104–9110. [Google Scholar] [CrossRef]
- Wang, Z.; Zhang, Y.; Zhang, P.; Yan, D.; Liu, J.; Chen, Y.; Liu, Q.; Cheng, P.; Zaworotko, M.J.; Zhang, Z. Thermally rearranged covalent organic framework with flame-retardancy as a high safety Li-ion solid electrolyte. eScience 2022, 2, 311–318. [Google Scholar] [CrossRef]
- Tolganbek, N.; Yerkinbekova, Y.; Kalybekkyzy, S.; Bakenov, Z.; Mentbayeva, A. Current state of high voltage olivine structured LiMPO4 cathode materials for energy storage applications: A review. J. Alloys Compd. 2021, 882, 160774. [Google Scholar] [CrossRef]
- Van der Jagt, R.; Vasileiadis, A.; Veldhuizen, H.; Shao, P.; Feng, X.; Ganapathy, S.; Habisreutinger, N.C.; van der Veen, M.A.; Wang, C.; Wagemaker, M.; et al. Synthesis and Structure–Property Relationships of Polyimide Covalent Organic Frameworks for Carbon Dioxide Capture and (Aqueous) Sodium-Ion Batteries. Chem. Mater. 2021, 33, 818–833. [Google Scholar] [CrossRef]
- Jeong, K.; Park, S.; Jung, G.Y.; Kim, S.H.; Lee, Y.-H.; Kwak, S.K.; Lee, S.-Y. Solvent-Free, Single Lithium-Ion Conducting Covalent Organic Frameworks. J. Am. Chem. Soc. 2019, 141, 5880–5885. [Google Scholar] [CrossRef] [PubMed]
- Cheng, D.; Sun, C.; Lang, Z.; Zhang, J.; Hu, A.; Duan, J.; Chen, X.; Zang, H.-Y.; Chen, J.; Zheng, M.; et al. Hybrid covalent organic-framework-based electrolytes for optimizing interface resistance in solid-state lithium-ion batteries. Cell Rep. Phys. Sci. 2022, 3, 100731. [Google Scholar] [CrossRef]
- Nagai, A.; Chen, X.; Feng, X.; Ding, X.; Guo, Z.; Jiang, D. A Squaraine-Linked Mesoporous Covalent Organic Framework. Angew. Chem. Int. Ed. 2013, 52, 3770–3774. [Google Scholar] [CrossRef] [PubMed]
- Qiao, W.; Li, Z. Recent Progress of Squaraine-Based Fluorescent Materials and Their Biomedical Applications. Symmetry 2022, 14, 966. [Google Scholar] [CrossRef]
- Wang, Y.; Geng, S.; Yan, G.; Liu, X.; Zhang, X.; Feng, Y.; Shi, J.; Qu, X. A Squaraine-Linked Zwitterionic Covalent Organic Framework Nanosheets Enhanced Poly(ethylene oxide) Composite Polymer Electrolyte for Quasi-Solid-State Li–S Batteries. ACS Appl. Energy Mater. 2022, 5, 2495–2504. [Google Scholar] [CrossRef]
- Cheng, Z.; Lu, L.; Zhang, S.; Liu, H.; Xing, T.; Lin, Y.; Ren, H.; Li, Z.; Zhi, L.; Wu, M. Amphoteric covalent organic framework as single Li+ superionic conductor in all-solid-state. Nano Res. 2022, 16, 528–535. [Google Scholar] [CrossRef]
- Du, Y.; Yang, H.; Whiteley, J.M.; Wan, S.; Jin, Y.; Lee, S.; Zhang, W. Ionic Covalent Organic Frameworks with Spiroborate Linkage. Angew. Chem. 2016, 128, 1769–1773. [Google Scholar] [CrossRef]
- Vazquez-Molina, D.A.; Mohammad-Pour, G.S.; Lee, C.; Logan, M.W.; Duan, X.; Harper, J.K.; Uribe-Romo, F.J. Mechanically Shaped 2-Dimensional Covalent Organic Frameworks Reveal Crystallographic Alignment and Fast Li-Ion Conductivity. J. Am. Chem. Soc. 2016, 138, 9767–9770. [Google Scholar] [CrossRef] [PubMed]
- Usiskin, R.; Lu, Y.; Popovic, J.; Law, M.; Balaya, P.; Hu, Y.-S.; Maier, J. Fundamentals, status and promise of sodium-based batteries. Nat. Rev. Mater. 2021, 6, 1020–1035. [Google Scholar] [CrossRef]
- Min, X.; Xiao, J.; Fang, M.; Wang, W.; Zhao, Y.; Liu, Y.; Abdelkader, A.M.; Xi, K.; Kumar, R.V.; Huang, Z. Potassium-ion batteries: Outlook on present and future technologies. Energy Environ. Sci. 2021, 14, 2186–2243. [Google Scholar] [CrossRef]
- You, C.; Wu, X.; Yuan, X.; Chen, Y.; Liu, L.; Zhu, Y.; Fu, L.; Wu, Y.; Guo, Y.-G.; van Ree, T. Advances in rechargeable Mg batteries. J. Mater. Chem. A 2020, 8, 25601–25625. [Google Scholar] [CrossRef]
- Elia, G.A.; Kravchyk, K.V.; Kovalenko, M.V.; Chacón, J.; Holland, A.; Wills, R.G. An overview and prospective on Al and Al-ion battery technologies. J. Power Sources 2021, 481, 228870. [Google Scholar] [CrossRef]
- Wang, N.; Wan, H.; Duan, J.; Wang, X.; Tao, L.; Zhang, J. A review of zinc-based battery from alkaline to acid. Mater. Today Adv. 2021, 11, 100149. [Google Scholar] [CrossRef]
Disclaimer/Publisher’s Note: The statements, opinions and data contained in all publications are solely those of the individual author(s) and contributor(s) and not of MDPI and/or the editor(s). MDPI and/or the editor(s) disclaim responsibility for any injury to people or property resulting from any ideas, methods, instructions or products referred to in the content. |
© 2023 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (https://creativecommons.org/licenses/by/4.0/).
Share and Cite
Polczyk, T.; Nagai, A. Covalent Organic Framework-Based Electrolytes for Lithium Solid-State Batteries—Recent Progress. Batteries 2023, 9, 469. https://doi.org/10.3390/batteries9090469
Polczyk T, Nagai A. Covalent Organic Framework-Based Electrolytes for Lithium Solid-State Batteries—Recent Progress. Batteries. 2023; 9(9):469. https://doi.org/10.3390/batteries9090469
Chicago/Turabian StylePolczyk, Tomasz, and Atsushi Nagai. 2023. "Covalent Organic Framework-Based Electrolytes for Lithium Solid-State Batteries—Recent Progress" Batteries 9, no. 9: 469. https://doi.org/10.3390/batteries9090469