Investigation of the Redox
Chemistry of Isoindole-4,7-diones
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Abstract
Quinone derivatives have been proposed as active components
in
lithium ion battery (LIB) electrode materials. In this work the electrochemistry
of a series of substituted isoindole-4,7-diones (IIDs) was investigated.
Three new IID derivatives were synthesized and characterized by various
electrochemical and spectroscopic techniques. Polymerization was attempted
to achieve a conducting polymer with redox active quinone side groups,
which would be advantageous in a LIB application. A combination of <i>in situ</i> spectroelectrochemical measurements and density
functional theory (DFT) calculations was used to investigate the proton
coupled redox reactions of the IIDs. Results from a previous computational
study of the IIDs were compared with experimental data here, and the
agreement was very good. The energy of the spectroscopic transitions
in the UV and in the visible region showed different correlation with
redox potential and quinone substituent in the series of IIDs. This
behavior was rationalized by examination of the involved molecular
orbitals. The results indicated that the properties of the quinone
unit, such as the redox potential, could be selectively varied by
substitution