Investigation of the redox chemistry of isoindole-4,7-diones

Christoffer Karlsson, Adolf Gogoll, Maria Strømme, Martin Sjödin

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22 Citations (Scopus)

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 in situ 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.

Original languageEnglish
Pages (from-to)894-901
Number of pages8
JournalJournal of Physical Chemistry C
Volume117
Issue number2
DOIs
Publication statusPublished - 2013 Jan 17
Externally publishedYes

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ASJC Scopus subject areas

  • Electronic, Optical and Magnetic Materials
  • Energy(all)
  • Surfaces, Coatings and Films
  • Physical and Theoretical Chemistry

Cite this

Karlsson, C., Gogoll, A., Strømme, M., & Sjödin, M. (2013). Investigation of the redox chemistry of isoindole-4,7-diones. Journal of Physical Chemistry C, 117(2), 894-901. https://doi.org/10.1021/jp311009z