Soluble and stable symmetric tetrazines as anolytes in redox flow batteries

Gloria D. De La Garza, Aman Preet Kaur, Ilya A. Shkrob, Lily A. Robertson, Susan A. Odom, Anne J. McNeil

Research output: Contribution to journalArticlepeer-review

5 Scopus citations


Nonaqueous redox flow batteries are a promising technology for grid-scale energy storage, however, their commercial success relies on identifying redox-active materials that exhibit extreme potentials, high solubilities in all states of charge, and long cycling stabilities. Meeting these requirements has been particularly challenging for molecules capable of storing negative charge. Within this context, tetrazines remain unexplored despite their unique structural properties that enable them to meet some of these challenges. Herein, we prepared symmetric s-tetrazines substituted with methyl, methoxy, and thiomethyl substituents and evaluated their electrochemical properties, solubility, and cycling stability. These studies revealed that highly soluble 3,6-dimethoxy-s-tetrazine undergoes a reversible one-electron reduction to generate a stable (t1/2 > 1240 h) radical anion. When implemented in a lab-scale symmetric flow cell (0.125 M), it exhibited a relatively slow capacity fade of 8% over 50 cycles (17 h). Given their high solubility and cycling stability, we believe that s-tetrazine derivatives should be further explored for nonaqueous redox flow batteries.

Original languageEnglish
Pages (from-to)18745-18752
Number of pages8
JournalJournal of Materials Chemistry A
Issue number36
StatePublished - Aug 18 2022

Bibliographical note

Funding Information:
This paper is dedicated to the memory of Susan A. Odom, a fierce and creative scientist, and cherished member of the JCESR team. This research was supported by the Department of Energy through the Joint Center for Energy Storage Research (JCESR), an Energy Innovation Hub funded by the U.S. Department of Energy, Office of Science, Basic Energy Sciences. GDD thanks the National Science Foundation for a Graduate Research Fellowship. The authors thank Prof. Melanie Sanford (and the Sanford group) for helpful discussions, and Jessica L. Tami for performing the catholyte compatibility experiments. The submitted manuscript has been created by UChicago Argonne, LLC, Operator of Argonne National Laboratory (“Argonne”). Argonne, a U.S. Department of Energy Office of Science laboratory, is operated under contract no. DE-AC02-06CH11357. The U.S. Government retains for itself, and others acting on its behalf, a paid-up nonexclusive, irrevocable worldwide license in said article to reproduce, prepare derivative works, distribute copies to the public, and perform publicly and display publicly, by or on behalf of the Government.

Publisher Copyright:
© 2022 The Royal Society of Chemistry.

ASJC Scopus subject areas

  • Chemistry (all)
  • Renewable Energy, Sustainability and the Environment
  • Materials Science (all)


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