Issue 2, 2019

A 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 solubilization while not penalizing gravimetric capacity remains a challenge. Here we propose the concept of a 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 chemical, yet with unusual thermal stability and low solubility in battery electrolytes. These properties 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.

Graphical abstract: A H-bond stabilized quinone electrode material for Li–organic batteries: the strength of weak bonds

Supplementary files

Article information

Article type
Edge Article
Submitted
06 Jul 2018
Accepted
09 Oct 2018
First published
09 Oct 2018
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY-NC license

Chem. Sci., 2019,10, 418-426

A H-bond stabilized quinone electrode material for Li–organic batteries: the strength of weak bonds

L. Sieuw, A. Jouhara, É. Quarez, C. Auger, J. Gohy, P. Poizot and A. Vlad, Chem. Sci., 2019, 10, 418 DOI: 10.1039/C8SC02995D

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