Synthesis and Characterization of a Molecularly Designed High-Performance Organodisulfide as Cathode Material for Lithium Batteries
Abstract
An innovative organodisulfide compound, 2,3,4,6,8,9,10,12–Octathia biscyclopenta[b,c]–5,11–anthraquinone–1,7–dithione (TPQD), has been successfully designed, synthesized, and characterized as a cathode material for lithium batteries. A benzoquinone is introduced to coordinate with dithiolane through 1,4–dithianes. The molecular structure, electrochemical performances, and the lithiation/delithiation mechanism of the TPQD cathode have been systematically investigated. TPQD can deliver an initial capacity of 251.7 mAh g-1 at a rate of C/10, which corresponds to the transfer of 4.7 electrons per formula. Highly reversible capacities and stable cyclic performances can be achieved at rates from C/10 to 5 C. Very interestingly, TPQD can retain a capacity of 120 mAh g-1 after 200 cycles at the 5 C rate, which is quite impressive for organodisulfide compounds. X–ray absorption spectroscopy measurements and density functional theory calculation results suggest that such a high capacity is contributed by both O redox of the quinone group and the cleavage and recombination of the disulfide bond. Moreover, the extended π–conjugation structure of the material, introduced by benzoquinone and dithiane, is beneficial for improving the high rate capability and cyclic stability. Furthermore this study illustrates an innovative approach in designing new organodisulfide compounds with improved cyclability and rate capability as cathode materials for high performance lithiummore »
- Authors:
-
[1];
[1]
- Brookhaven National Lab. (BNL), Upton, NY (United States)
- Jingdezhen Ceramic Institute, Jingdezhen (China)
- Canadian Light Source, Saskatoon (Canada)
- Stony Brook Univ., Stony Brook, NY (United States)
- Publication Date:
- Research Org.:
- Brookhaven National Laboratory (BNL), Upton, NY (United States)
- Sponsoring Org.:
- USDOE Office of Science (SC), Basic Energy Sciences (BES); USDOE Office of Energy Efficiency and Renewable Energy (EERE), Vehicle Technologies Office (EE-3V)
- OSTI Identifier:
- 1507114
- Alternate Identifier(s):
- OSTI ID: 1506702
- Report Number(s):
- BNL-211534-2019-JAAM
Journal ID: ISSN 1614-6832
- Grant/Contract Number:
- SC0012704
- Resource Type:
- Accepted Manuscript
- Journal Name:
- Advanced Energy Materials
- Additional Journal Information:
- Journal Volume: 9; Journal Issue: 21; Journal ID: ISSN 1614-6832
- Publisher:
- Wiley
- Country of Publication:
- United States
- Language:
- English
- Subject:
- 25 ENERGY STORAGE; organodisulfide; lithium battery; high rate; soft X ray absorption spectroscopy
Citation Formats
Shadike, Zulipiya, Lee, Hung ‐Sui, Tian, Chuanjin, Sun, Ke, Song, Liang, Hu, Enyuan, Waluyo, Iradwikanari, Hunt, Adrian, Ghose, Sanjit, Hu, Yongfeng, Zhou, Jigang, Wang, Jian, Northrup, Paul, Bak, Seong ‐Min, and Yang, Xiao ‐Qing. Synthesis and Characterization of a Molecularly Designed High-Performance Organodisulfide as Cathode Material for Lithium Batteries. United States: N. p., 2019.
Web. doi:10.1002/aenm.201900705.
Shadike, Zulipiya, Lee, Hung ‐Sui, Tian, Chuanjin, Sun, Ke, Song, Liang, Hu, Enyuan, Waluyo, Iradwikanari, Hunt, Adrian, Ghose, Sanjit, Hu, Yongfeng, Zhou, Jigang, Wang, Jian, Northrup, Paul, Bak, Seong ‐Min, & Yang, Xiao ‐Qing. Synthesis and Characterization of a Molecularly Designed High-Performance Organodisulfide as Cathode Material for Lithium Batteries. United States. https://doi.org/10.1002/aenm.201900705
Shadike, Zulipiya, Lee, Hung ‐Sui, Tian, Chuanjin, Sun, Ke, Song, Liang, Hu, Enyuan, Waluyo, Iradwikanari, Hunt, Adrian, Ghose, Sanjit, Hu, Yongfeng, Zhou, Jigang, Wang, Jian, Northrup, Paul, Bak, Seong ‐Min, and Yang, Xiao ‐Qing. Wed .
"Synthesis and Characterization of a Molecularly Designed High-Performance Organodisulfide as Cathode Material for Lithium Batteries". United States. https://doi.org/10.1002/aenm.201900705. https://www.osti.gov/servlets/purl/1507114.
@article{osti_1507114,
title = {Synthesis and Characterization of a Molecularly Designed High-Performance Organodisulfide as Cathode Material for Lithium Batteries},
author = {Shadike, Zulipiya and Lee, Hung ‐Sui and Tian, Chuanjin and Sun, Ke and Song, Liang and Hu, Enyuan and Waluyo, Iradwikanari and Hunt, Adrian and Ghose, Sanjit and Hu, Yongfeng and Zhou, Jigang and Wang, Jian and Northrup, Paul and Bak, Seong ‐Min and Yang, Xiao ‐Qing},
abstractNote = {An innovative organodisulfide compound, 2,3,4,6,8,9,10,12–Octathia biscyclopenta[b,c]–5,11–anthraquinone–1,7–dithione (TPQD), has been successfully designed, synthesized, and characterized as a cathode material for lithium batteries. A benzoquinone is introduced to coordinate with dithiolane through 1,4–dithianes. The molecular structure, electrochemical performances, and the lithiation/delithiation mechanism of the TPQD cathode have been systematically investigated. TPQD can deliver an initial capacity of 251.7 mAh g-1 at a rate of C/10, which corresponds to the transfer of 4.7 electrons per formula. Highly reversible capacities and stable cyclic performances can be achieved at rates from C/10 to 5 C. Very interestingly, TPQD can retain a capacity of 120 mAh g-1 after 200 cycles at the 5 C rate, which is quite impressive for organodisulfide compounds. X–ray absorption spectroscopy measurements and density functional theory calculation results suggest that such a high capacity is contributed by both O redox of the quinone group and the cleavage and recombination of the disulfide bond. Moreover, the extended π–conjugation structure of the material, introduced by benzoquinone and dithiane, is beneficial for improving the high rate capability and cyclic stability. Furthermore this study illustrates an innovative approach in designing new organodisulfide compounds with improved cyclability and rate capability as cathode materials for high performance lithium batteries.},
doi = {10.1002/aenm.201900705},
journal = {Advanced Energy Materials},
number = 21,
volume = 9,
place = {United States},
year = {Wed Apr 10 00:00:00 EDT 2019},
month = {Wed Apr 10 00:00:00 EDT 2019}
}
Free Publicly Available Full Text
Publisher's Version of Record
Other availability
Search WorldCat to find libraries that may hold this journal
Cited by: 29 works
Citation information provided by
Web of Science
Web of Science
Save to My Library
You must Sign In or Create an Account in order to save documents to your library.
Works referenced in this record:
Recent Progress in Organic Electrodes for Li and Na Rechargeable Batteries
journal, March 2018
- Lee, Sechan; Kwon, Giyun; Ku, Kyojin
- Advanced Materials, Vol. 30, Issue 42
Investigation into the use of quinone compounds-for battery cathodes
journal, May 1972
- Alt, H.; Binder, H.; Köhling, A.
- Electrochimica Acta, Vol. 17, Issue 5
Anthracene based organodisulfide positive active materials for lithium secondary battery
journal, October 2003
- Xue, L. J.; Li, J. X.; Hu, S. Q.
- Electrochemistry Communications, Vol. 5, Issue 10
A Novel Class of Organosulfur Electrodes for Energy Storage
journal, January 1989
- Visco, Steven J.
- Journal of The Electrochemical Society, Vol. 136, Issue 3
Aniline-based polyorganodisulfide redox system of high energy for secondary lithium batteries
journal, June 2004
- Li, Jinxia; Zhan, Hui; Zhou, Lei
- Electrochemistry Communications, Vol. 6, Issue 6
High-performance lithium–organic batteries by achieving 16 lithium storage in poly(imine-anthraquinone)
journal, January 2019
- Man, Zengming; Li, Peng; Zhou, Dong
- Journal of Materials Chemistry A, Vol. 7, Issue 5
Sulfur K-edge X-ray absorption spectroscopy for determining the chemical speciation of sulfur in biological systems
journal, December 1998
- Pickering, Ingrid J.; Prince, Roger C.; Divers, Thomas
- FEBS Letters, Vol. 441, Issue 1
Sulfur: not a “silent” element any more
journal, January 2006
- Jalilehvand, Farideh
- Chem. Soc. Rev., Vol. 35, Issue 12
Conducting polymers and their inorganic composites for advanced Li-ion batteries: a review
journal, January 2015
- Sengodu, Prakash; Deshmukh, Abhay D.
- RSC Advances, Vol. 5, Issue 52
Benzene-based polyorganodisulfide cathode materials for secondary lithium batteries
journal, March 2006
- Deng, Shi-Ren; Kong, Ling-Bo; Hu, Gao-Qiang
- Electrochimica Acta, Vol. 51, Issue 13
Electrochemical behavior of polyamides with cyclic disulfide structure and their application to positive active material for lithium secondary battery
journal, January 2001
- Tsutsumi, Hiromori; Oyari, Yoshiaki; Onimura, Kenjiro
- Journal of Power Sources, Vol. 92, Issue 1-2
Structure-Related Electrochemistry of Sulfur-Poly(acrylonitrile) Composite Cathode Materials for Rechargeable Lithium Batteries
journal, November 2011
- Fanous, Jean; Wegner, Marcus; Grimminger, Jens
- Chemistry of Materials, Vol. 23, Issue 22
Polyanthra[1,9,8-b,c,d,e][4,10,5-b,c,d,e]bis-[1,6,6a(6a-S) trithia]pentalene-active material for cathode of lithium secondary battery with unusually high specific capacity
journal, October 2006
- Liu, Z. J.; Kong, L. B.; Zhou, Y. H.
- Journal of Power Sources, Vol. 161, Issue 2
High-performance Lithium Secondary Batteries Using Cathode Active Materials of Triquinoxalinylenes Exhibiting Six Electron Migration
journal, July 2011
- Matsunaga, Takayuki; Kubota, Takayuki; Sugimoto, Toyonari
- Chemistry Letters, Vol. 40, Issue 7, p. 750-752
Ambient Temperature High-Rate Lithium/Organosulfur Batteries
journal, January 1990
- Visco, S. J.
- Journal of The Electrochemical Society, Vol. 137, Issue 4
Electrochemical Behaviors of Naphtho[1,8-cd][1,2]dithiol, Dibenzo[c,e][1,2]dithiin, and Naphtho[1,8-cd:4,5-cʹdʹ]bis[1,2]dithiol
journal, January 2003
- Inamasu, Tokuo; Yoshitoku, Daisuke; Sumi-otorii, Yukihisa
- Journal of The Electrochemical Society, Vol. 150, Issue 1
On the Way Toward Understanding Solution Chemistry of Lithium Polysulfides for High Energy Li-S Redox Flow Batteries
journal, April 2015
- Pan, Huilin; Wei, Xiaoliang; Henderson, Wesley A.
- Advanced Energy Materials, Vol. 5, Issue 16
Electrochemical properties of PABTH as cathode materials for rechargeable lithium battery
journal, May 2007
- Li, Yajuan; Zhan, Hui; Kong, Lingbo
- Electrochemistry Communications, Vol. 9, Issue 5, p. 1217-1221
Chemical polymerization of pyrrole with disulfide structure and the application to lithium secondary batteries
journal, February 2006
- Amaike, Masato; Iihama, Teruyuki
- Synthetic Metals, Vol. 156, Issue 2-4
Azo Compounds Derived from Electrochemical Reduction of Nitro Compounds for High Performance Li-Ion Batteries
journal, April 2018
- Luo, Chao; Ji, Xiao; Hou, Singyuk
- Advanced Materials, Vol. 30, Issue 23
A Novel cathode material based on polyaniline used for lithium/sulfur secondary battery
journal, September 2010
- Zhang, Shi-chao; Zhang, Lan; Wang, Wei-kun
- Synthetic Metals, Vol. 160, Issue 17-18
A new mixing of Hartree–Fock and local density‐functional theories
journal, January 1993
- Becke, Axel D.
- The Journal of Chemical Physics, Vol. 98, Issue 2
High Sulfur Content Material with Stable Cycling in Lithium-Sulfur Batteries
journal, October 2017
- Preefer, Molleigh B.; Oschmann, Bernd; Hawker, Craig J.
- Angewandte Chemie International Edition, Vol. 56, Issue 47
Organic Electrode Materials for Rechargeable Lithium Batteries
journal, May 2012
- Liang, Yanliang; Tao, Zhanliang; Chen, Jun
- Advanced Energy Materials, Vol. 2, Issue 7
Quantitative and Qualitative Determination of Polysulfide Species in the Electrolyte of a Lithium-Sulfur Battery using HPLC ESI/MS with One-Step Derivatization
journal, January 2015
- Zheng, Dong; Qu, Deyu; Yang, Xiao-Qing
- Advanced Energy Materials, Vol. 5, Issue 16
A density functional theory study on the thermodynamic and dynamic properties of anthraquinone analogue cathode materials for rechargeable lithium ion batteries
journal, January 2017
- Yang, Shu-Jing; Qin, Xiao-Ya; He, Rongxing
- Physical Chemistry Chemical Physics, Vol. 19, Issue 19
PDFgetX2: a GUI-driven program to obtain the pair distribution function from X-ray powder diffraction data
journal, July 2004
- Qiu, Xiangyun; Thompson, Jeroen W.; Billinge, Simon J. L.
- Journal of Applied Crystallography, Vol. 37, Issue 4, p. 678-678
An Insoluble Benzoquinone-Based Organic Cathode for Use in Rechargeable Lithium-Ion Batteries
journal, August 2017
- Luo, Zhiqiang; Liu, Luojia; Zhao, Qing
- Angewandte Chemie International Edition, Vol. 56, Issue 41
Design Strategies for Promising Organic Positive Electrodes in Lithium-Ion Batteries: Quinones and Carbon Materials
journal, October 2017
- Kim, Ki Chul
- Industrial & Engineering Chemistry Research, Vol. 56, Issue 42
Redox-Active Organic Sodium Anthraquinone-2-Sulfonate (AQS) Anchored on Reduced Graphene Oxide for High-Performance Supercapacitors
journal, September 2018
- Shi, Ruiying; Han, Cuiping; Duan, Huan
- Advanced Energy Materials, Vol. 8, Issue 31
Review—Advanced Carbon-Supported Organic Electrode Materials for Lithium (Sodium)-Ion Batteries
journal, January 2015
- Zhu, Zhiqiang; Chen, Jun
- Journal of The Electrochemical Society, Vol. 162, Issue 14
Ionic Conductivity of Organosulfur Melts for Advanced Storage Electrodes
journal, January 1988
- Visco, Steven J.
- Journal of The Electrochemical Society, Vol. 135, Issue 12
IFEFFIT : interactive XAFS analysis and FEFF fitting
journal, March 2001
- Newville, Matthew
- Journal of Synchrotron Radiation, Vol. 8, Issue 2
Quinone Electrode Materials for Rechargeable Lithium/Sodium Ion Batteries
journal, May 2017
- Wu, Yiwen; Zeng, Ronghua; Nan, Junmin
- Advanced Energy Materials, Vol. 7, Issue 24
Dimercaptan–polyaniline composite electrodes for lithium batteries with high energy density
journal, February 1995
- Oyama, N.; Tatsuma, T.; Sato, T.
- Nature, Vol. 373, Issue 6515
Poly(ethene-1,1,2,2-tetrathiol): Novel cathode material with high specific capacity for rechargeable lithium batteries
journal, January 2009
- Zhang, Jingyu; Song, Zhiping; Zhan, Lizhi
- Journal of Power Sources, Vol. 186, Issue 2
Polymer-Based Organic Batteries
journal, August 2016
- Muench, Simon; Wild, Andreas; Friebe, Christian
- Chemical Reviews, Vol. 116, Issue 16
Two-dimensional detector software: From real detector to idealised image or two-theta scan
journal, January 1996
- Hammersley, A. P.; Svensson, S. O.; Hanfland, M.
- High Pressure Research, Vol. 14, Issue 4-6, p. 235-248
Electrochemical Behaviors of Hexathiadipentalene Ring, Dithiol Ring, and Methyl Sulfide Groups on Anthracene Derivatives Confined on Electrode
journal, January 2010
- Sarukawa, Tomoo; Yamaguchi, Shuichirou; Oyama, Noboru
- Journal of The Electrochemical Society, Vol. 157, Issue 12
Lithium storage in conductive sulfur-containing polymers
journal, November 2004
- Yu, Xian-guo; Xie, Jing-ying; Yang, Jun
- Journal of Electroanalytical Chemistry, Vol. 573, Issue 1
An Insoluble Benzoquinone-Based Organic Cathode for Use in Rechargeable Lithium-Ion Batteries
journal, August 2017
- Luo, Zhiqiang; Liu, Luojia; Zhao, Qing
- Angewandte Chemie, Vol. 129, Issue 41
High Sulfur Content Material with Stable Cycling in Lithium-Sulfur Batteries
journal, October 2017
- Preefer, Molleigh B.; Oschmann, Bernd; Hawker, Craig J.
- Angewandte Chemie, Vol. 129, Issue 47
Lithium storage in conductive sulfur-containing polymers
journal, November 2004
- Yu, Xian-guo; Xie, Jing-ying; Yang, Jun
- Journal of Electroanalytical Chemistry, Vol. 573, Issue 1, p. 121-128
Sulfur: Not a “Silent” Element Any More
journal, May 2007
- Jalilehvand, Farideh
- ChemInform, Vol. 38, Issue 18
Magnetosomes could be protective shields against metal stress in magnetotactic bacteria
journal, July 2020
- Muñoz, D.; Marcano, L.; Martín-Rodríguez, R.
- Scientific Reports, Vol. 10, Issue 1