Article

A redox-flow battery with an alloxazine-based organic electrolyte

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Abstract

Redox-flow batteries (RFBs) can store large amounts of electrical energy from variable sources, such as solar and wind. Recently, redox-active organic molecules in aqueous RFBs have drawn substantial attention due to their rapid kinetics and low membrane crossover rates. Drawing inspiration from nature, here we report a high-performance aqueous RFB utilizing an organic redox compound, alloxazine, which is a tautomer of the isoalloxazine backbone of vitamin B2. It can be synthesized in high yield at room temperature by single-step coupling of inexpensive o-phenylenediamine derivatives and alloxan. The highly alkaline-soluble alloxazine 7/8-carboxylic acid produces a RFB exhibiting open-circuit voltage approaching 1.2 V and current efficiency and capacity retention exceeding 99.7% and 99.98% per cycle, respectively. Theoretical studies indicate that structural modification of alloxazine with electron-donating groups should allow further increases in battery voltage. As an aza-aromatic molecule that undergoes reversible redox cycling in aqueous electrolyte, alloxazine represents a class of radical-free redox-active organics for use in large-scale energy storage.

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Author information

Affiliations

  1. Department of Chemistry and Chemical Biology, Harvard University, 12 Oxford Street, Cambridge, Massachusetts 02138, USA

    • Kaixiang Lin
    • , Rafael Gómez-Bombarelli
    • , Eugene S. Beh
    • , Liuchuan Tong
    • , Alán Aspuru-Guzik
    •  & Roy G. Gordon
  2. Harvard John A. Paulson School of Engineering and Applied Sciences, 29 Oxford Street, Cambridge, Massachusetts 02138, USA

    • Eugene S. Beh
    • , Qing Chen
    • , Michael J. Aziz
    •  & Roy G. Gordon
  3. Harvard College, Cambridge, Massachusetts 02138, USA

    • Alvaro Valle

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Contributions

K.L., R.G.G. and M.J.A. formulated the project. K.L. and L.T. synthesized the compounds. K.L., E.S.B. and L.T. collected and analysed the NMR data. K.L., Q.C., E.S.B. and A.V. collected and analysed the electrochemical data. K.L. and A.V. measured solubility. R.G.-B. and A.A.-G. performed theoretical analysis. K.L., R.G.G. and M.J.A. wrote the paper, and all authors contributed to revising the paper.

Competing interests

The authors declare no competing financial interests.

Corresponding authors

Correspondence to Michael J. Aziz or Roy G. Gordon.

Supplementary information

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    Supplementary Information

    Supplementary Figures 1–13, Supplementary Table 1–2.