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H-bond Stabilized Quinone Electrode Material for Li-Organic Batteries: the Strength of Weak Bonds

Abstract

Small organic materials are generally plagued by their high solubility in battery electrolytes. Finding approaches to suppress the solubilization while not penalizing the gravimetric capacity remains a persisting challenge. Here we propose the concept of Hydrogen-bond stabilized organic battery framework as a viable solution. This is illustrated for 2,5-diamino-1,4-benzoquinone (DABQ), an electrically neutral and low mass organic chemistry, yet with unusual thermal stability and low solubility in battery electrolytes. These are shown to arise from hydrogen bond molecular crystal stabilization, confirmed by a suite of techniques including X-ray diffraction and infrared spectroscopy. We also establish a quantitative correlation between the electrolyte solvent polarity, molecular structure of the electrolyte and DABQ solubility - then correlate these to the cycling stability. Notably, DABQ displays a highly reversible (above 99%) sequential 2-electron electrochemical activity in the solid phase, a process rarely observed for similar small molecular battery chemistries. Taken together, these results reveal a potential new strategy towards stable and practical organic battery chemistries through intramolecular hydrogen-bonding crystal stabilization.

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Publication details

The article was received on 06 Jul 2018, accepted on 09 Oct 2018 and first published on 09 Oct 2018


Article type: Edge Article
DOI: 10.1039/C8SC02995D
Citation: Chem. Sci., 2018, Accepted Manuscript
  • Open access: Creative Commons BY-NC license
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    H-bond Stabilized Quinone Electrode Material for Li-Organic Batteries: the Strength of Weak Bonds

    L. Sieuw, A. Jouhara, E. Quarez, C. Auger, J. Gohy, P. Poizot and A. Vlad, Chem. Sci., 2018, Accepted Manuscript , DOI: 10.1039/C8SC02995D

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