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Title: Annulated Dialkoxybenzenes as Catholyte Materials for Non-aqueous Redox Flow Batteries: Achieving High Chemical Stability through Bicyclic Substitution

Abstract

Abstract 1,4‐Dimethoxybenzene derivatives are materials of choice for use as catholytes in non‐aqueous redox flow batteries, as they exhibit high open‐circuit potentials and excellent electrochemical reversibility. However, chemical stability of these materials in their oxidized form needs to be improved. Disubstitution in the arene ring is used to suppress parasitic reactions of their radical cations, but this does not fully prevent ring‐addition reactions. By incorporating bicyclic substitutions and ether chains into the dialkoxybenzenes, a novel catholyte molecule, 9,10‐bis(2‐methoxyethoxy)‐1,2,3,4,5,6,7,8‐octahydro‐1,4:5,8‐dimethanenoanthracene (BODMA), is obtained and exhibits greater solubility and superior chemical stability in the charged state. A hybrid flow cell containing BODMA is operated for 150 charge–discharge cycles with a minimal loss of capacity.

Authors:
 [1];  [2];  [1];  [1];  [1];  [3];  [2];  [1];  [1];  [1];  [1];  [1];  [1];  [2];  [1];  [3];  [2];  [1]
+ Show Author Affiliations
  1. Argonne National Lab. (ANL), Argonne, IL (United States)
  2. Argonne National Lab. (ANL), Argonne, IL (United States); Pacific Northwest National Lab. (PNNL), Richland, WA (United States)
  3. Argonne National Lab. (ANL), Argonne, IL (United States); Univ. of Michigan, Ann Arbor, MI (United States)
Publication Date:
Research Org.:
Argonne National Laboratory (ANL), Argonne, IL (United States)
Sponsoring Org.:
USDOE Office of Science (SC), Basic Energy Sciences (BES) (SC-22), Joint Center for Energy Storage Research (JCESR); USDOE
OSTI Identifier:
1402467
Alternate Identifier(s):
OSTI ID: 1401299
Grant/Contract Number:  
AC02-06CH11357
Resource Type:
Accepted Manuscript
Journal Name:
Advanced Energy Materials
Additional Journal Information:
Journal Volume: 2017; Journal ID: ISSN 1614-6832
Publisher:
Wiley
Country of Publication:
United States
Language:
English
Subject:
25 ENERGY STORAGE; 36 MATERIALS SCIENCE; bicyclic substitution; catholyte materials; nonaqueous redox flow batteries; para-dialkoxybenzene

Citation Formats

Zhang, Jingjing, Yang, Zheng, Shkrob, Ilya A., Assary, Rajeev S., Tung, Siu on, Silcox, Benjamin, Duan, Wentao, Zhang, Junjie, Su, Chi Cheung, Hu, Bin, Pan, Baofei, Liao, Chen, Zhang, Zhengcheng, Wang, Wei, Curtiss, Larry A., Thompson, Levi T., Wei, Xiaoliang, and Zhang, Lu. Annulated Dialkoxybenzenes as Catholyte Materials for Non-aqueous Redox Flow Batteries: Achieving High Chemical Stability through Bicyclic Substitution. United States: N. p., 2017. Web. doi:10.1002/aenm.201701272.
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Zhang, Jingjing, Yang, Zheng, Shkrob, Ilya A., Assary, Rajeev S., Tung, Siu on, Silcox, Benjamin, Duan, Wentao, Zhang, Junjie, Su, Chi Cheung, Hu, Bin, Pan, Baofei, Liao, Chen, Zhang, Zhengcheng, Wang, Wei, Curtiss, Larry A., Thompson, Levi T., Wei, Xiaoliang, & Zhang, Lu. Annulated Dialkoxybenzenes as Catholyte Materials for Non-aqueous Redox Flow Batteries: Achieving High Chemical Stability through Bicyclic Substitution. United States. https://doi.org/10.1002/aenm.201701272
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Zhang, Jingjing, Yang, Zheng, Shkrob, Ilya A., Assary, Rajeev S., Tung, Siu on, Silcox, Benjamin, Duan, Wentao, Zhang, Junjie, Su, Chi Cheung, Hu, Bin, Pan, Baofei, Liao, Chen, Zhang, Zhengcheng, Wang, Wei, Curtiss, Larry A., Thompson, Levi T., Wei, Xiaoliang, and Zhang, Lu. Fri . "Annulated Dialkoxybenzenes as Catholyte Materials for Non-aqueous Redox Flow Batteries: Achieving High Chemical Stability through Bicyclic Substitution". United States. https://doi.org/10.1002/aenm.201701272. https://www.osti.gov/servlets/purl/1402467.
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@article{osti_1402467,
title = {Annulated Dialkoxybenzenes as Catholyte Materials for Non-aqueous Redox Flow Batteries: Achieving High Chemical Stability through Bicyclic Substitution},
author = {Zhang, Jingjing and Yang, Zheng and Shkrob, Ilya A. and Assary, Rajeev S. and Tung, Siu on and Silcox, Benjamin and Duan, Wentao and Zhang, Junjie and Su, Chi Cheung and Hu, Bin and Pan, Baofei and Liao, Chen and Zhang, Zhengcheng and Wang, Wei and Curtiss, Larry A. and Thompson, Levi T. and Wei, Xiaoliang and Zhang, Lu},
abstractNote = {Abstract 1,4‐Dimethoxybenzene derivatives are materials of choice for use as catholytes in non‐aqueous redox flow batteries, as they exhibit high open‐circuit potentials and excellent electrochemical reversibility. However, chemical stability of these materials in their oxidized form needs to be improved. Disubstitution in the arene ring is used to suppress parasitic reactions of their radical cations, but this does not fully prevent ring‐addition reactions. By incorporating bicyclic substitutions and ether chains into the dialkoxybenzenes, a novel catholyte molecule, 9,10‐bis(2‐methoxyethoxy)‐1,2,3,4,5,6,7,8‐octahydro‐1,4:5,8‐dimethanenoanthracene (BODMA), is obtained and exhibits greater solubility and superior chemical stability in the charged state. A hybrid flow cell containing BODMA is operated for 150 charge–discharge cycles with a minimal loss of capacity.},
doi = {10.1002/aenm.201701272},
journal = {Advanced Energy Materials},
number = ,
volume = 2017,
place = {United States},
year = {Fri Jul 21 00:00:00 EDT 2017},
month = {Fri Jul 21 00:00:00 EDT 2017}
}
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https://doi.org/10.1002/aenm.201701272
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    A Two-Electron Storage Nonaqueous Organic Redox Flow Battery
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    Asymmetric allyl-activation of organosulfides for high-energy reversible redox flow batteries
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    High-Performance Oligomeric Catholytes for Effective Macromolecular Separation in Nonaqueous Redox Flow Batteries
    journal, January 2018

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