Computational Electrochemistry Study of 16 Isoindole-4,7-diones as Candidates for Organic Cathode Materials

Abstract

Prediction of the redox behavior of electroactive molecules enables screening of a variety of compounds and can serve as a guideline in the search for organic molecules for use as cathode materials in, for example, Li ion batteries. In this study, we present a computational strategy, based on density functional theory, to calculate redox potentials and acid dissociation constants for a series of 16 isoindole-4,7-dione (IID) derivatives. The calculations take all possible electron and proton transfers into account, and the results were found to correlate very well with electrochemical and spectroscopic measurements. The possibility of polymerizing the IID derivatives was also assessed computationally, as polymerization serves as a straightforward route to immobilize the active material. Three of the considered IIDs (5,6-dicyano-2-methyl-isoindole-4,7-dione, 5,6-dihydroxy-2-methyl-isoindole-4,7-dione, and 2-methyl-5-(trifluoromethyl)-isoindole-4,7-dione) are predicted to be particularly interesting for maki...