Electrochimica Acta, Vol.228, 494-502, 2017
Synthesis and Electrochemical Study of a TCAA Derivative - A potential bipolar redox-active material
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 E-1/2 = 1.42 V vs. Fc(+)/Fc with a peak split of 96 mV and a quasi-reversible reduction and re-oxidation at E-1/2 =-1.49 V vs. Fc(+)/Fc with a peak split of 174 mV, which lead to a theoretical potential difference of 2.91 V. (C) 2017 Elsevier Ltd. All rights reserved.