Synthesis and Electrochemical Study of a TCAA Derivative – A potential bipolar redox-active material

Hagemann, Tino; Winsberg, Jan; Wild, Andy; Schubert, Ulrich S.

Abstract:

The 2,3,7,8-tetracyano-1,4,5,6,9,10-hexazaanthracene (TCAA) derivatives represent an interesting substance class for future research on organic electronic devices, such as solar cells, organic batteries or redox-flow batteries (RFBs). Because of their multivalent redox behavior they are potentially “bipolar”, usable both as cathode and anode activ charge-storage materials. Furthermore, they show a strong absorption and fluorescence behavior both in solution and solid state, rendering them a promising emitter for electroluminescence devices, like lamps or displays. In order to evaluate a TCAA for electrochemical applications the derivative 2,3,7,8-tetracyano-5,10-diphenyl-5,10-dihydrodipyrazino[2,3-b:2′,3′-e]pyrazine (2) was synthesized in two straightforward synthesis steps. The electrochemical behavior of 2 was initially determined by density functional theory (DFT) calculation and afterwards investigated via rotating disc electrode (RDE), UV–vis–NIR spectroelectrochemical as well as cyclic voltammetry (CV) measurements. It features a quasi-reversible oxidation and re-reduction at E½ = 1.42 V vs. Fc+/Fc with a peak split of 96 mV and a quasi-reversible reduction and re-oxidation at E½ = −1.49 V vs. Fc+/Fc with a peak split of 174 mV, which lead to a theoretical potential difference of 2.91 V.

Research areas:

• Polymer Batteries

Year:

2017

Type of Publication:

Article

Journal:

Electrochimica Acta

Volume:

228

Pages:

494 - 520

DOI:

10.1016/j.electacta.2017.01.055