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              <p>Raising the operating potential of the organic positive electrode materials is a crucial challenge if they are to compare with lithium-ion inorganic counterparts. Although many efforts have been directed on tuning through substituent electronic effect, the chemistries than can operate above 3 V vs Li + /Li 0 , and thus be air stable in the Li-reservoir form (alike the conventional inorganic Liion positive electrode materials) remain finger-counted. Herein, we report on a new n-type organic Li-ion positive electrode materialthe tetralithium 2,5dihydroxy-1,4-benzenediacetatewith a remarkably high redox potential of 3.35 V vs Li + /Li attained notably in the solid phase. The origin of the high-energy content in this quinone derivative is found in a stereoelectronic chameleonic effect with an intramolecular conformation change and charge modulation leading to a redox potential increase of 650 mV in the solid state as compared to the same chemistry tested in solution (2.70 V vs Li + /Li). The conformational dependent electroactivity rationale is supported by electrochemical and crystallography analysis, comparative infrared spectroscopy, and DFT calculation. We identify and make a linear correlation between the enolate vibrational modes and the redox potential, with general applicability for possibly other phenolate redox chemistries. Owing to these effects, this lithiated quinone is stable in ambient air and can be processed and handled alike the conventional inorganic Li-ion positive electrode materials. Whereas intrinsic to high voltage operation stability issues remain to be solved for practical implementation, our fundamental in nature and proof-of-concept study highlights the strong amplitude of through-space charge modulation effects in designing new organic Li-ion positive electrode chemistries with practical operating potential.</p>
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