Thianthrene-Based Bipolar Redox-Active Molecules Toward Symmetric All-Organic Batteries

Samuel I. Etkind, Jeffrey Lopez, Yun Guang Zhu, Jen Hung Fang, Wen Jie Ong, Yang Shao-Horn, Timothy M. Swager*

*Corresponding author for this work

Research output: Contribution to journalArticlepeer-review

4 Scopus citations


Bipolar redox activity is generally obtained using a single moiety that can be both oxidized and reduced or by tethering two distinct redox active molecules, together with a covalent linker. Herein, we demonstrate an alternative approach using the SNAr and SNAr-type reactions of benzene-1,2-dithiols and electron-deficient aromatic halides or halogenated quinones to prepare a family of compact, thianthrene-based bifunctional molecules. The potential of these molecules as electrolytes for redox flow batteries was assessed in static cells as a proof of concept. Cycling in a static cell demonstrated that the thianthrene-quinone, PQtBuTH (8), is highly stable, compared to other symmetric organic active materials, with 44% capacity retention over 450 cycles (16.7 days), and an initial energy density of 1.3Wh/L at a concentration of 0.1 M. Redox flow batteries represent a promising grid-scale energy storage technology, and the development of new symmetric electrolyte systems in organic solvents can potentially mitigate issues associated with membrane crossover and provide high cell voltages.

Original languageEnglish (US)
Pages (from-to)11739-11750
Number of pages12
JournalACS Sustainable Chemistry and Engineering
Issue number36
StatePublished - Sep 12 2022


  • Electrochemistry
  • Electrolyte
  • Redox Flow Battery
  • Static Cell
  • Symmetric Battery

ASJC Scopus subject areas

  • Chemistry(all)
  • Environmental Chemistry
  • Chemical Engineering(all)
  • Renewable Energy, Sustainability and the Environment


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