Reversible Redox Chemistry of Azo Compounds for Sodium-Ion Batteries

Luo, Chao; Xu, Gui-Liang; Ji, Xiao; Hou, Singyuk; Chen, Long; Wang, Fei; Jiang, Jianjun; Chen, Zonghai; Ren, Yang; Amine, Khalil; Wang, Chunsheng

doi:10.1002/anie.201713417

Reversible Redox Chemistry of Azo Compounds for Sodium-Ion Batteries

Journal Article · Sun Jan 28 23:00:00 EST 2018 · Angewandte Chemie (International Edition)

DOI:https://doi.org/10.1002/anie.201713417· OSTI ID:1426720

Luo, Chao ^[1]; Xu, Gui-Liang ^[2]; Ji, Xiao ^[3]; Hou, Singyuk ^[1]; Chen, Long ^[1]; Wang, Fei ^[1]; Jiang, Jianjun ^[4]; Chen, Zonghai ^[2]; Ren, Yang ^[2]; Amine, Khalil ^[5]; ^[1]

Univ. of Maryland, College Park, MD (United States)
Argonne National Lab. (ANL), Argonne, IL (United States)
Univ. of Maryland, College Park, MD (United States); Huazhong Univ. of Science and Technology, Wuhan (China)
Huazhong Univ. of Science and Technology, Wuhan (China)
Argonne National Lab. (ANL), Argonne, IL (United States); Imam Abdulrahman Bin Faisal Univ., Dammam (Saudi Arabia)

Sustainable sodium-ion batteries (SSIBs) using renewable organic electrodes are promising alternatives to lithium-ion batteries for the large-scale renewable energy storage. However, the lack of high-performance anode material impedes the development of SSIBs. Herein, we report a new type of organic anode material based on azo group for SSIBs. Azobenzene-4,4'-dicarboxylic acid sodium salt is used as a model to investigate the electrochemical behaviors and reaction mechanism of azo compound. It exhibits a reversible capacity of 170 mAhg^-1 at 0.2C. When current density is increased to 20C, the reversible capacities of 98 mAhg^-1 can be retained for 2000 cycles, demonstrating excellent cycling stability and high rate capability. The detailed characterizations reveal that azo group acts as an electrochemical active site to reversibly bond with Na⁺. The reversible redox chemistry between azo compound and Na ions offer opportunities for developing longcycle-life and high-rate SSIBs.

View Accepted Manuscript (DOE)

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

Sponsoring Organization:: National Science Foundation (NSF); USDOE Office of Energy Efficiency and Renewable Energy (EERE), Vehicle Technologies Office (EE-3V)

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1426720

Journal Information:: Angewandte Chemie (International Edition), Journal Name: Angewandte Chemie (International Edition) Journal Issue: 11 Vol. 57; ISSN 1433-7851

Publisher:: WileyCopyright Statement

Country of Publication:: United States

Language:: English

References (39)

Vibrational characterization of azobenzenes, azoxybenzenes and azoaromatic and azoxyaromatic polyethers Tecklenburg, Mary M. J.; Kosnak, Derek J.; Bhatnagar, Atul Journal of Raman Spectroscopy, Vol. 28, Issue 10 https://doi.org/10.1002/(SICI)1097-4555(199710)28:10<755::AID-JRS143>3.0.CO;2-V	journal	October 1997
Sodium Terephthalate as an Organic Anode Material for Sodium Ion Batteries Park, Yuwon; Shin, Dong-Seon; Woo, Seung Hee Advanced Materials, Vol. 24, Issue 26 https://doi.org/10.1002/adma.201201205	journal	June 2012
A High-Energy Room-Temperature Sodium-Sulfur Battery Xin, Sen; Yin, Ya-Xia; Guo, Yu-Guo Advanced Materials, Vol. 26, Issue 8 https://doi.org/10.1002/adma.201304126	journal	December 2013
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
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
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
Charge and Discharge Processes and Sodium Storage in Disodium Pyridine-2,5-Dicarboxylate Anode-Insights from Experiments and Theory Padhy, Harihara; Chen, Yingqian; Lüder, Johann Advanced Energy Materials, Vol. 8, Issue 7 https://doi.org/10.1002/aenm.201701572	journal	November 2017
Redox Cofactor from Biological Energy Transduction as Molecularly Tunable Energy-Storage Compound Lee, Minah; Hong, Jihyun; Seo, Dong-Hwa Angewandte Chemie, Vol. 125, Issue 32 https://doi.org/10.1002/ange.201301850	journal	June 2013
All Organic Sodium-Ion Batteries with Na ₄ C ₈ H ₂ O ₆ Wang, Shiwen; Wang, Lijiang; Zhu, Zhiqiang Angewandte Chemie, Vol. 126, Issue 23 https://doi.org/10.1002/ange.201400032	journal	February 2014
Polymeric Schiff Bases as Low-Voltage Redox Centers for Sodium-Ion Batteries Castillo-Martínez, Elizabeth; Carretero-González, Javier; Armand, Michel Angewandte Chemie, Vol. 126, Issue 21 https://doi.org/10.1002/ange.201402402	journal	April 2014
Use of Graphite as a Highly Reversible Electrode with Superior Cycle Life for Sodium-Ion Batteries by Making Use of Co-Intercalation Phenomena Jache, Birte; Adelhelm, Philipp Angewandte Chemie, Vol. 126, Issue 38 https://doi.org/10.1002/ange.201403734	journal	July 2014
Oxocarbon Salts for Fast Rechargeable Batteries Zhao, Qing; Wang, Jianbin; Lu, Yong Angewandte Chemie, Vol. 128, Issue 40 https://doi.org/10.1002/ange.201607194	journal	September 2016
Redox Cofactor from Biological Energy Transduction as Molecularly Tunable Energy-Storage Compound Lee, Minah; Hong, Jihyun; Seo, Dong-Hwa Angewandte Chemie International Edition, Vol. 52, Issue 32 https://doi.org/10.1002/anie.201301850	journal	June 2013
All Organic Sodium-Ion Batteries with Na ₄ C ₈ H ₂ O ₆ Wang, Shiwen; Wang, Lijiang; Zhu, Zhiqiang Angewandte Chemie International Edition, Vol. 53, Issue 23 https://doi.org/10.1002/anie.201400032	journal	February 2014
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
Use of Graphite as a Highly Reversible Electrode with Superior Cycle Life for Sodium-Ion Batteries by Making Use of Co-Intercalation Phenomena Jache, Birte; Adelhelm, Philipp Angewandte Chemie International Edition, Vol. 53, Issue 38 https://doi.org/10.1002/anie.201403734	journal	July 2014
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
Self-Healing Chemistry between Organic Material and Binder for Stable Sodium-Ion Batteries Luo, Chao; Fan, Xiulin; Ma, Zhaohui Chem, Vol. 3, Issue 6 https://doi.org/10.1016/j.chempr.2017.09.004	journal	December 2017
Carbon coated hollow Na2FePO4F spheres for Na-ion battery cathodes Langrock, Alex; Xu, Yunhua; Liu, Yihang Journal of Power Sources, Vol. 223 https://doi.org/10.1016/j.jpowsour.2012.09.059	journal	February 2013
Graphene oxide wrapped croconic acid disodium salt for sodium ion battery electrodes Luo, Chao; Zhu, Yujie; Xu, Yunhua Journal of Power Sources, Vol. 250 https://doi.org/10.1016/j.jpowsour.2013.10.131	journal	March 2014
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
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
A Highly Reversible Room-Temperature Sodium Metal Anode Seh, Zhi Wei; Sun, Jie; Sun, Yongming ACS Central Science, Vol. 1, Issue 8 https://doi.org/10.1021/acscentsci.5b00328	journal	November 2015
A New Class of Lithium and Sodium Rechargeable Batteries Based on Selenium and Selenium–Sulfur as a Positive Electrode Abouimrane, Ali; Dambournet, Damien; Chapman, Karena W. Journal of the American Chemical Society, Vol. 134, Issue 10 https://doi.org/10.1021/ja211766q	journal	February 2012
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
Selenium@Mesoporous Carbon Composite with Superior Lithium and Sodium Storage Capacity Luo, Chao; Xu, Yunhua; Zhu, Yujie ACS Nano, Vol. 7, Issue 9 https://doi.org/10.1021/nn403108w	journal	August 2013
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
P2-type Nax[Fe1/2Mn1/2]O2 made from earth-abundant elements for rechargeable Na batteries Yabuuchi, Naoaki; Kajiyama, Masataka; Iwatate, Junichi Nature Materials, Vol. 11, Issue 6 https://doi.org/10.1038/nmat3309	journal	April 2012
P2-NaxVO2 system as electrodes for batteries and electron-correlated materials Guignard, Marie; Didier, Christophe; Darriet, Jacques Nature Materials, Vol. 12, Issue 1 https://doi.org/10.1038/nmat3478	journal	November 2012
High-rate electrochemical energy storage through Li+ intercalation pseudocapacitance Augustyn, Veronica; Come, Jérémy; Lowe, Michael A. Nature Materials, Vol. 12, Issue 6 https://doi.org/10.1038/nmat3601	journal	April 2013
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
Advanced intermediate-temperature Na–S battery Lu, Xiaochuan; Kirby, Brent W.; Xu, Wu Energy Environ. Sci., Vol. 6, Issue 1 https://doi.org/10.1039/C2EE23606K	journal	January 2013
Comparison of electrochemical performances of olivine NaFePO ₄ in sodium-ion batteries and olivine LiFePO ₄ in lithium-ion batteries Zhu, Yujie; Xu, Yunhua; Liu, Yihang Nanoscale, Vol. 5, Issue 2 https://doi.org/10.1039/C2NR32758A	journal	January 2013
Na _0.67 Mn _1−x Mg _x O ₂ (0 ≤ x ≤ 0.2): a high capacity cathode for sodium-ion batteries Billaud, Juliette; Singh, Gurpreet; Armstrong, A. Robert Energy Environ. Sci., Vol. 7, Issue 4 https://doi.org/10.1039/C4EE00465E	journal	January 2014
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
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
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
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
Synthesis of New Azo Compounds Based on N-(4-Hydroxypheneyl)maleimide and N-(4-Methylpheneyl)maleimide Mohammed, Issam Ahmed; Mustapha, Asniza Molecules, Vol. 15, Issue 10 https://doi.org/10.3390/molecules15107498	journal	October 2010

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