Applicationof density functional calculations to compute electrochemical propertiessuch as redox windows, effect of substitution by electron donatingand electron withdrawing groups on redox windows, and solvation freeenergies for ∼50 anthraquinone (AQ) derivatives are presentedbecause of their potential as anolytes in all-organic redox flow batteries.Computations suggest that lithium ions can increase (by ∼0.4V) the reduction potential of anthraquinone due to the lithium ionpairing by forming a Lewis base–Lewis acid complex. To designnew redox active species, the substitution by electron donating groupsis essential to improve the reduction window of AQ with adequate oxidativestability. For instance, a complete methylation of AQ can improveits reduction window by ∼0.4 V. The quantum chemical studiesof the ∼50 AQ derivatives are used to derive a relationshipthat connects the computed LUMO energy and the reduction potentialthat can be applied as a descriptor for screening thousands of AQderivatives. Our computations also suggest that incorporating oxy-methyldioxolane substituents in the AQ framework can increase its interactionwith nonaqueous solvent and improve its solubility. Thermochemicalcalculations for likely bond breaking decomposition reactions of unsubstitutedAQ anions suggest that the dianions are relatively stable in the solution.These studies provide an ideal platform to perform further combinedexperimental and theoretical studies to understand the electrochemicalreversibility and solubility of new quinone molecules as energy storagematerials. [ABSTRACT FROM AUTHOR]