A Scalable Synthesis of a New Quasi‐Reversible Redox Compound with a High Positive Redox Potential

Organic redox species are used in redox flow batteries, redox‐mediated CO 2 capture, and catalysis. Organic molecules with high redox potentials, e.g., TEMPO, have found use as oxidation agents and as catalysts in organic chemistry. This study presents a synthesis route to make new organic redox‐active molecule, 1,4‐diallyl‐2,5‐bis(allyloxy)benzene. The compound is electrochemically reversible with a formal redox potential of +1.45 V/standard hydrogen electrode (SHE). To unveil the electrochemical reaction mechanism of 1,4‐diallyl‐2,5‐bis(allyloxy)benzene, a series of different organic molecules are synthesized and electrochemically characterized. Together with a series of chemical oxidation experiments supported by NMR, the electrochemical mechanism of the quasi‐reversible electron transfer is suggested. The oxidation of 1,4‐diallyl‐2,5‐bis(allyloxy)benzene leads to a formation of an organic cation radical, which is stabilized by allyl groups, and can be reverted to upon electrochemical reduction. Overall, 1,4‐diallyl‐2,5‐bis(allyloxy)benzene is a new, electrochemically quasi‐reversible redox molecule, with a very high redox potential, that can find application in redox flow batteries, catalysis, and organic chemistry, as oxidant.