Establishing substitution rules of functional groups for high-capacity organic anode materials in Na-ion batteries

Holguin, Kathryn; Qin, Kaiqiang; Kamphaus, Ethan Phillip; Chen, Fu; Cheng, Lei; Xu, Gui-Liang; Amine, Khalil; Luo, Chao

doi:10.1016/j.jpowsour.2022.231383

Title: Establishing substitution rules of functional groups for high-capacity organic anode materials in Na-ion batteries

Journal Article · 02 April 2022 · Journal of Power Sources

DOI: https://doi.org/10.1016/j.jpowsour.2022.231383 · OSTI ID:1880098

Holguin, Kathryn ^[1]; Qin, Kaiqiang ^[1];

^[2]; Chen, Fu ^[3]; Cheng, Lei ^[2]; Xu, Gui-Liang ^[2]; Amine, Khalil ^[4];

^[1]

George Mason Univ., Fairfax, VA (United States)
Argonne National Lab. (ANL), Lemont, IL (United States)
Univ. of Maryland, College Park, MD (United States)
Argonne National Lab. (ANL), Lemont, IL (United States); Stanford Univ., CA (United States)

Tailoring molecular structures of organic electrode materials (OEMs) can enhance their performance in Na-ion batteries, however, the substitution rules and the consequent effect on the specific capacity and working potential remain elusive. Herein, by examining three sodium carboxylates with selective N substitution or extended conjugation structure, we exploited the correlation between structure and performance to establish substitution rules for high-capacity OEMs. Our results show that substitution position and types of functional groups are essential to create active centers for uptake/removal of Na+ and thermodynamically stabilize organic structures. Furthermore, rational host design and electrolytes modulation were performed to extend the cycle life to 500 cycles. A full cell based on the optimal 2,2’-bipyridine-4,4’-dicarboxylic acid disodium salt anode and the polyaniline cathode is demonstrated to confirm the feasibility of achieving all-organic batteries. Lastly, this work provides a valuable guideline for the design principle of high-capacity and stable OEMs for sustainable energy storage.

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Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States)

Sponsoring Organization:: USDOE Office of Energy Efficiency and Renewable Energy (EERE), Transportation Office. Vehicle Technologies Office - Battery Materials Research (BMR) Program; National Science Foundation (NSF)

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1880098

Journal Information:: Journal of Power Sources, Journal Name: Journal of Power Sources Vol. 533; ISSN 0378-7753

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

References (44)

Advances in Organic Anode Materials for Na‐/K‐Ion Rechargeable Batteries Desai, Aamod V.; Morris, Russell E.; Armstrong, A. Robert ChemSusChem, Vol. 13, Issue 18 https://doi.org/10.1002/cssc.202001334	journal	August 2020
Disodium Terephthalate (Na2C8H4O4) as High Performance Anode Material for Low-Cost Room-Temperature Sodium-Ion Battery Zhao, Liang; Zhao, Junmei; Hu, Yong-Sheng Advanced Energy Materials, Vol. 2, Issue 8 https://doi.org/10.1002/aenm.201200166	journal	May 2012
A highly conductive conjugated coordination polymer for fast-charge sodium-ion batteries: reconsidering its structures Wu, Yanchao; Chen, Yuan; Tang, Mi Chemical Communications, Vol. 55, Issue 73 https://doi.org/10.1039/C9CC05679C	journal	January 2019
Sodium insertion in carboxylate based materials and their application in 3.6 V full sodium cells Abouimrane, Ali; Weng, Wei; Eltayeb, Hussameldin Energy & Environmental Science, Vol. 5, Issue 11, p. 9632-9638 https://doi.org/10.1039/c2ee22864e	journal	January 2012
Oxocarbon Salts for Fast Rechargeable Batteries Zhao, Qing; Wang, Jianbin; Lu, Yong Angewandte Chemie International Edition, Vol. 55, Issue 40 https://doi.org/10.1002/anie.201607194	journal	September 2016
Extended π-Conjugated System for Fast-Charge and -Discharge Sodium-Ion Batteries Wang, Chengliang; Xu, Yang; Fang, Yaoguo Journal of the American Chemical Society, Vol. 137, Issue 8 https://doi.org/10.1021/jacs.5b00336	journal	February 2015
Polymer-Based Organic Batteries Muench, Simon; Wild, Andreas; Friebe, Christian Chemical Reviews, Vol. 116, Issue 16 https://doi.org/10.1021/acs.chemrev.6b00070	journal	August 2016
Recent progress on sodium ion batteries: potential high-performance anodes Li, Li; Zheng, Yang; Zhang, Shilin Energy & Environmental Science, Vol. 11, Issue 9 https://doi.org/10.1039/C8EE01023D	journal	January 2018
Aromatic porous-honeycomb electrodes for a sodium-organic energy storage device Sakaushi, Ken; Hosono, Eiji; Nickerl, Georg Nature Communications, Vol. 4, Issue 1 https://doi.org/10.1038/ncomms2481	journal	February 2013
Carbonyls: Powerful Organic Materials for Secondary Batteries Häupler, Bernhard; Wild, Andreas; Schubert, Ulrich S. Advanced Energy Materials, Vol. 5, Issue 11 https://doi.org/10.1002/aenm.201402034	journal	April 2015
Molecular engineering of covalent organic nanosheets for high-performance sodium-ion batteries Kim, Min-Sung; Lee, Minseop; Kim, Min-Jae Journal of Materials Chemistry A, Vol. 8, Issue 34 https://doi.org/10.1039/D0TA06206E	journal	January 2020
Polymeric Schiff Bases as Low-Voltage Redox Centers for Sodium-Ion Batteries Castillo-Martínez, Elizabeth; Carretero-González, Javier; Armand, Michel Angewandte Chemie International Edition, Vol. 53, Issue 21 https://doi.org/10.1002/anie.201402402	journal	April 2014
Polyimide@Ketjenblack Composite: A Porous Organic Cathode for Fast Rechargeable Potassium‐Ion Batteries Zhang, Chenglin; Xu, Yang; He, Kaiming Small, Vol. 16, Issue 38 https://doi.org/10.1002/smll.202002953	journal	August 2020
Organic Thiocarboxylate Electrodes for a Room-Temperature Sodium-Ion Battery Delivering an Ultrahigh Capacity Zhao, Hongyang; Wang, Jianwei; Zheng, Yuheng Angewandte Chemie, Vol. 129, Issue 48 https://doi.org/10.1002/ange.201708960	journal	November 2017
Recent Progress in Organic Electrodes for Li and Na Rechargeable Batteries Lee, Sechan; Kwon, Giyun; Ku, Kyojin Advanced Materials, Vol. 30, Issue 42 https://doi.org/10.1002/adma.201704682	journal	March 2018
Biologically inspired pteridine redox centres for rechargeable batteries Hong, Jihyun; Lee, Minah; Lee, Byungju Nature Communications, Vol. 5, Issue 1 https://doi.org/10.1038/ncomms6335	journal	October 2014
Nitrogen-rich covalent organic frameworks with multiple carbonyls for high-performance sodium batteries Shi, Ruijuan; Liu, Luojia; Lu, Yong Nature Communications, Vol. 11, Issue 1 https://doi.org/10.1038/s41467-019-13739-5	journal	January 2020
Dual Rate-Modulation Approach for the Preparation of Crystalline Covalent Triazine Frameworks Displaying Efficient Sodium Storage Yang, Na; Gu, Yanqing; Shan, Yilin ACS Macro Letters, Vol. 11, Issue 1 https://doi.org/10.1021/acsmacrolett.1c00591	journal	December 2021
Azo compounds as a family of organic electrode materials for alkali-ion batteries Luo, Chao; Borodin, Oleg; Ji, Xiao Proceedings of the National Academy of Sciences, Vol. 115, Issue 9 https://doi.org/10.1073/pnas.1717892115	journal	February 2018
Highly durable organic electrode for sodium-ion batteries via a stabilized α-C radical intermediate Wu, Shaofei; Wang, Wenxi; Li, Minchan Nature Communications, Vol. 7, Issue 1 https://doi.org/10.1038/ncomms13318	journal	November 2016
Oligomeric-Schiff bases as negative electrodes for sodium ion batteries: unveiling the nature of their active redox centers López-Herraiz, María; Castillo-Martínez, Elizabeth; Carretero-González, Javier Energy & Environmental Science, Vol. 8, Issue 11 https://doi.org/10.1039/C5EE01832C	journal	January 2015
An Organic Pigment as a High-Performance Cathode for Sodium-Ion Batteries Luo, Wei; Allen, Marshall; Raju, Vadivukarasi Advanced Energy Materials, Vol. 4, Issue 15 https://doi.org/10.1002/aenm.201400554	journal	June 2014
Na-ion batteries, recent advances and present challenges to become low cost energy storage systems Palomares, Verónica; Serras, Paula; Villaluenga, Irune Energy & Environmental Science, Vol. 5, Issue 3 https://doi.org/10.1039/c2ee02781j	journal	January 2012
Advanced Organic Electrode Materials for Rechargeable Sodium-Ion Batteries Zhao, Qing; Lu, Yong; Chen, Jun Advanced Energy Materials, Vol. 7, Issue 8 https://doi.org/10.1002/aenm.201601792	journal	December 2016
Reversible Redox Chemistry of Azo Compounds for Sodium-Ion Batteries Luo, Chao; Xu, Gui-Liang; Ji, Xiao Angewandte Chemie International Edition, Vol. 57, Issue 11 https://doi.org/10.1002/anie.201713417	journal	February 2018
A conjugated tetracarboxylate anode for stable and sustainable Na-ion batteries Qin, Kaiqiang; Holguin, Kathryn; Mohammadiroudbari, Motahareh Chemical Communications, Vol. 57, Issue 19 https://doi.org/10.1039/D0CC08273B	journal	January 2021
Organic electrode materials for non-aqueous, aqueous, and all-solid-state Na-ion batteries Holguin, Kathryn; Mohammadiroudbari, Motahareh; Qin, Kaiqiang Journal of Materials Chemistry A, Vol. 9, Issue 35 https://doi.org/10.1039/D1TA00528F	journal	January 2021
Sodium-Ion Batteries Slater, Michael D.; Kim, Donghan; Lee, Eungje Advanced Functional Materials, Vol. 23, Issue 8, p. 947-958 https://doi.org/10.1002/adfm.201200691	journal	May 2012
Hexacyanoferrate‐Type Prussian Blue Analogs: Principles and Advances Toward High‐Performance Sodium and Potassium Ion Batteries Zhou, Aijun; Cheng, Weijie; Wang, Wei Advanced Energy Materials, Vol. 11, Issue 2 https://doi.org/10.1002/aenm.202000943	journal	May 2020
The rise of organic electrode materials for energy storage Schon, Tyler B.; McAllister, Bryony T.; Li, Peng-Fei Chemical Society Reviews, Vol. 45, Issue 22 https://doi.org/10.1039/C6CS00173D	journal	January 2016
Roll-to-roll fabrication of organic nanorod electrodes for sodium ion batteries Luo, Chao; Wang, Jingjing; Fan, Xiulin Nano Energy, Vol. 13 https://doi.org/10.1016/j.nanoen.2015.03.041	journal	April 2015
Regulating Steric Hindrance in Redox‐Active Porous Organic Frameworks Achieves Enhanced Sodium Storage Performance (Small 1/2022) Shan, Yilin; He, Yanyan; Yang, Na Small, Vol. 18, Issue 1 https://doi.org/10.1002/smll.202270004	journal	January 2022
Opportunities and Challenges for Organic Electrodes in Electrochemical Energy Storage Poizot, Philippe; Gaubicher, Joël; Renault, Stéven Chemical Reviews, Vol. 120, Issue 14 https://doi.org/10.1021/acs.chemrev.9b00482	journal	March 2020
Research Development on Sodium-Ion Batteries Yabuuchi, Naoaki; Kubota, Kei; Dahbi, Mouad Chemical Reviews, Vol. 114, Issue 23 https://doi.org/10.1021/cr500192f	journal	October 2014
Recent advances in developing organic electrode materials for multivalent rechargeable batteries Qin, Kaiqiang; Huang, Jinghao; Holguin, Kathryn Energy & Environmental Science, Vol. 13, Issue 11 https://doi.org/10.1039/D0EE02111C	journal	January 2020
Redox‐Active Organic Compounds for Future Sustainable Energy Storage System Lee, Sechan; Hong, Jihyun; Kang, Kisuk Advanced Energy Materials, Vol. 10, Issue 30 https://doi.org/10.1002/aenm.202001445	journal	June 2020
Organic materials for rechargeable sodium-ion batteries Xu, Yang; Zhou, Min; Lei, Yong Materials Today, Vol. 21, Issue 1 https://doi.org/10.1016/j.mattod.2017.07.005	journal	January 2018
A Pyrazine‐Based Polymer for Fast‐Charge Batteries Mao, Minglei; Luo, Chao; Pollard, Travis P. Angewandte Chemie International Edition, Vol. 58, Issue 49 https://doi.org/10.1002/anie.201910916	journal	December 2019
Room-temperature stationary sodium-ion batteries for large-scale electric energy storage Pan, Huilin; Hu, Yong-Sheng; Chen, Liquan Energy & Environmental Science, Vol. 6, Issue 8 https://doi.org/10.1039/c3ee40847g	journal	January 2013
How Many Lithium Ions Can Be Inserted onto Fused C ₆ Aromatic Ring Systems? Han, Xiaoyan; Qing, Guangyan; Sun, Jutang Angewandte Chemie International Edition, Vol. 51, Issue 21 https://doi.org/10.1002/anie.201109187	journal	April 2012
High-performance sodium–organic battery by realizing four-sodium storage in disodium rhodizonate Lee, Minah; Hong, Jihyun; Lopez, Jeffrey Nature Energy, Vol. 2, Issue 11 https://doi.org/10.1038/s41560-017-0014-y	journal	October 2017
Covalent–Organic Frameworks: Advanced Organic Electrode Materials for Rechargeable Batteries Sun, Tao; Xie, Jian; Guo, Wei Advanced Energy Materials, Vol. 10, Issue 19 https://doi.org/10.1002/aenm.201904199	journal	April 2020
Organic Electrode Materials for Metal Ion Batteries Shea, John J.; Luo, Chao ACS Applied Materials & Interfaces, Vol. 12, Issue 5 https://doi.org/10.1021/acsami.9b20384	journal	January 2020
Sodium storage in triazine-based molecular organic electrodes: The importance of hydroxyl substituents Shan, Yilin; He, Yanyan; Gu, Yanqing Chemical Engineering Journal, Vol. 430 https://doi.org/10.1016/j.cej.2021.133055	journal	February 2022

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25 ENERGY STORAGE
Sodium carboxylate
Organic electrode materials
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Substitution rules

Title: Establishing substitution rules of functional groups for high-capacity organic anode materials in Na-ion batteries

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