Jump to main content
Jump to site search


A stable two-electron-donating phenothiazine for application in nonaqueous redox flow batteries

Author affiliations

Abstract

Stable electron-donating organic compounds are of interest for numerous applications that require reversible electron-transfer reactions. Although many organic compounds are stable one-electron donors, removing a second electron from a small molecule to form its dication usually leads to rapid decomposition. For cost-effective electrochemical energy storage utilizing organic charge-storage species, the creation of high-capacity materials requires stabilizing more charge whilst keeping molecular weights low. Here we report the simple modification of N-ethylphenothiazine, which is only stable as a radical cation (not as a dication), and demonstrate that introducing electron-donating methoxy groups para to nitrogen leads to dramatically improved stability of the doubly oxidized (dication) state. Our results reveal that this derivative is more stable than an analogous compound with substituents that do not allow for further charge delocalization, rendering it a promising scaffold for developing atom-efficient, two-electron donors.

Graphical abstract: A stable two-electron-donating phenothiazine for application in nonaqueous redox flow batteries

Back to tab navigation

Supplementary files

Publication details

The article was received on 06 Jul 2017, accepted on 24 Oct 2017 and first published on 24 Oct 2017


Article type: Paper
DOI: 10.1039/C7TA05883G
Citation: J. Mater. Chem. A, 2017, Advance Article
  •   Request permissions

    A stable two-electron-donating phenothiazine for application in nonaqueous redox flow batteries

    J. A. Kowalski, M. D. Casselman, A. P. Kaur, J. D. Milshtein, C. F. Elliott, S. Modekrutti, N. H. Attanayake, N. Zhang, S. R. Parkin, C. Risko, F. R. Brushett and S. A. Odom, J. Mater. Chem. A, 2017, Advance Article , DOI: 10.1039/C7TA05883G

Search articles by author

Spotlight

Advertisements