Application of organic electrode materials in rechargeable batteries has attracted great interest because such materials contain abundant carbon, hydrogen, and oxygen elements. However, organic electrodes are highly soluble in organic electrolytes. An organic electrode of 2,3,5,6-tetraphthalimido-1,4-benzoquinone (TPB) is reported in which rigid groups coordinate to a molecular benzoquinone skeleton. The material is insoluble in aprotic electrolyte, and demonstrates a high capacity retention of 91.4 % (204 mA h g-1 ) over 100 cycles at 0.2 C. The extended π-conjugation of the material contributes to enhancement of the electrochemical performance (155 mA h g-1 at 10 C). Moreover, density functional theory calculations suggest that favorable synergistic reactions between multiple carbonyl groups and lithium ions can enhance the initial lithium ion intercalation potential. The described approach may provide a novel entry to next-generation organic electrode materials with relevance to lithium-ion batteries.
Keywords: benzoquinones; electronic conjugation; insolubility; lithium-ion batteries; rigid phthalimide groups.
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