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A Highly Soluble Redox Shuttle with Superior Rate Performance in Overcharge Protection

Published online by Cambridge University Press:  02 March 2015

Susan A. Odom,
Aman Kaur,
Selin Ergun,
Corrine F. Elliott and
Matthew D. Casselman
Susan A. Odom
Affiliation:
Department of Chemistry, University of Kentucky, Lexington, KY 40506, U.S.A.
Aman Kaur
Affiliation:
Department of Chemistry, University of Kentucky, Lexington, KY 40506, U.S.A.
Selin Ergun
Affiliation:
Department of Chemistry, University of Kentucky, Lexington, KY 40506, U.S.A.
Corrine F. Elliott
Affiliation:
Department of Chemistry, University of Kentucky, Lexington, KY 40506, U.S.A.
Matthew D. Casselman
Affiliation:
Department of Chemistry, University of Kentucky, Lexington, KY 40506, U.S.A.
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Abstract

The demand for a stable and compatible redox shuttles for use in lithium-ion batteries has prompted us to explore strategies to tune and improve the properties of redox shuttles. We have studied over 50 new diarylamine derivatives synthesized in our laboratory including one compound in which we introduced trifluoromethyl groups (–CF3) at the positions para to the nitrogen atom in N-ethylphenothiazine (EPT). The high electronegativity of the CF3 group raises the oxidation potential, and its incorporation also significantly increases solubility in battery electrolyte. Here we report 3,7-bis(trifluoromethyl)-N-ethylphenothiazine (BCF3EPT) as a new redox shuttle, which we have observed to have the highest reported solubility in battery electrolyte of all redox shuttles that maintain extended overcharge performance. We have compared its performance with 1,3-di-tert-butyl-2,5-dimethoxybenzene (DBB), EPT, and other robust redox shuttles. In our hands, overcharge cycling of BCF3EPT far surpasses any reported redox shuttle, and – because it can be dissolved at higher concentrations – it tolerates faster charging rates than both DBB and EPT.

Keywords

energy storageorganicchemical reaction

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References

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