Organic electrode materials have emerged as attractive alternatives to electrodes in Lithium-ion batteries produced from toxic and unsustainably-sourced transition metals. However, low-molecular-weight organic compounds still lack the cycling stability and high-rate capability found in transition metal electrodes. Recently, we reported S-rich thiazyl moieties as a new design feature for small-molecule organic electrode materials. Our findings suggest that S-rich thiazyl moieties engender strong SOMO-SOMO interactions that contribute to the insolubility and fast charging of low-molecular-weight quinones. This is demonstrated by the contrasting performance of three isomorphic bisthiazolyl quinones in solid-state: the S-rich quinone displays the strongest SOMO-SOMO interactions and can be cycled at a high rate of 10C for 400 cycles with 94% capacity retention, while the S-poor quinones display weak SOMO-SOMO interactions and suffer from dissolution and low cycling stabilities (&lt; 20 cycles). Our study indicates that introducing organic motifs that enable SOMO-SOMO stabilization could be a strategy to support favorable solid-state structures for energy storage applications. In our current work, we explore the generality of this strategy with two novel S-rich bisthiazolyl quinone isomers that possess distinct solid-state packing structures. Along with the parent S-rich bisthiazolyl quinone from our previous work, these isomers provide an effective means to determine if and how differences in atom connectivity and solid-state packing impacts the SOMO-SOMO interaction energy and the electrochemical performance of these materials in Li-ion batteries.

Bisthiazolyl quinones: Stabilizing organic electrode materials with sulfur-rich thiazyl motifs

Macromolecular Chemistry: The Second Century

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ACS Spring 2020 National Meeting & Expo

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