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. 2023 Jul 17;62(29):e202304600.
doi: 10.1002/anie.202304600. Epub 2023 Jun 7.

Phosphine Oxide-Functionalized Terthiophene Redox Systems

Daniel Käch  1 , Aurelio C Gasser  1 , Lionel Wettstein  1 , Clara Schweinzer  1 , Máté J Bezdek  1
Affiliations

Phosphine Oxide-Functionalized Terthiophene Redox Systems

Daniel Käch et al. Angew Chem Int Ed Engl. .

Abstract

Main group systems capable of undergoing controlled redox events at extreme potentials are elusive yet highly desirable for a range of organic electronics applications including use as energy storage media. Herein we describe phosphine oxide-functionalized terthiophenes that exhibit two reversible 1e- reductions at potentials below -2 V vs Fc/Fc+ (Fc=ferrocene) while retaining high degrees of stability. A phosphine oxide-functionalized terthiophene radical anion was synthesized in which the redox-responsive nature of the platform was established using combined structural, spectroscopic, and computational characterization. Straightforward structural modification led to the identification of a derivative that exhibits exceptional stability during bulk 2 e- galvanostatic charge-discharge cycling and enabled characterization of a 2 e- redox series. A new multi-electron redox system class is hence disclosed that expands the electrochemical cell potential range achievable with main group electrolytes without compromising stability.

Keywords: Electrochemistry; Electronic Structure; Functional Oligothiophenes; Main Group Radicals; Redox Chemistry.

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