Content not peer-reviewed by ChemRxiv. License: CC BY 4.0 The synthesis of DQC was done in an analogous way to the synthesis of TQC (Fig. ), and DQC was transformed to ODQC with oxidation in nitric acid. The ODQC was soluble in deuterated dimethyl sulfoxide (DMSO-d6), which enabled the characterization with liquid NMR spectroscopy. 1 H NMR spectrum revealed four peaks with equal integral values at 8.45, 8.37, 8.12 and 8.08 ppm corresponding to four distinguishable aromatic protons in ODQC (Fig. ). 13 The electrochemical performances of synthesized TQC and ODQC molecules were evaluated in a Swagelok Li-organic battery cell using 1 M lithium bis(trifluoromethanesulfonyl)imide (LiTFSI) in 1:1 (v/v) 1,3-dioxolane (DOL) and 1,2-dimethoxyethane (DME) as an electrolyte in the voltage range of 1.5 -3.8 V vs. Li/Li + . ODQC has a theoretical capacity of 515 mAhg -1 based on a six electron exchange reaction (Fig. ). Galvanostatic measurement of ODQC at 50 mAg -1 shows three distinct discharge plateaus at around 3.1 V, 2.9 V and 1.8 V. The system reached its highest capacity of 268 mAhg -1 in the first discharge with an average voltage of 2.58 V (Fig. ). The system exhibited fast capacity fading attributed to the dissolution of the active material in the electrolyte reaching 62.7 % and 16.8 % capacity retention in the 10 th and 300 th cycle, respectively (Fig. ). Fast capacity fading prevented us to conduct the rate performance test. A comparison of the galvanostatic measurements between ODQC and TQC clearly shows that the problem of solubility of the material in the electrolyte was mostly resolved, with TQC demonstrating a high 82.1 % capacity retention after 300 cycles at a low current density of 50 mA g -1 making it one of the most stable small organic cathode materials (Fig. ). The TQC possesses a theoretical capacity of 310 mAhg -1 based on a six electron exchange reaction and 517 mAhg -1 based on a ten electron exchange reaction including the outer quinoxaline units. Although the molecular structure was expanded with an additional redox active quinoxaline unit, we presume, that the full capacity could not be realized due to the redox activity of quinoxaline units lying below the stability window of the electrolyte. The system reached its highest capacity of 223 mAhg -1 in the first cycle with an average voltage of 2.42 V. In contrast to ODQC, the galvanostatic charge/discharge curves of TQC exhibited a sloping curve without distinct Content not peer-reviewed by ChemRxiv. License: CC BY 4.0 plateaus (Fig. ). The high cycling stability of TQC enabled to carry out rate performance test, where the material reached a capacity of 66 mAhg -1 (29 % of the maximum capacity) at a current density of 5 Ag -1 (Fig. ). The electrochemical performance of synthesized TQC and ODQC molecules was evaluated in a Swagelok Zn-organic battery cell using an aqueous solution of 3 M ZnSO4 as an electrolyte in the voltage window of 0.25 -1.6 V vs. Zn/Zn 2+ . Galvanostatic measurements of ODQC show slow activation with a gradual increase of capacity reaching a maximum value of 157 mAhg -1 at 50 mAg -1 in the 70 th cycle with an average discharge voltage of 0.56 V (Fig. ).