Scalable Synthesis and Characterisation of a Liquid 2,3,5,6-tetraallylbenzene-1,4-diol Quinone

Abstract

Organic redox species are finding uses in numerous research and development applications, such as electrochemical sensors, batteries, and production of chemicals. This paper presents a synthesis pathway of a redox-active liquid of 2,3,5,6-tetraallylbenzene-1,4-diol. The synthesis of 2,3,5,6-tetraallylbenzene-1,4-diol was found repeatable at approximately 60 g scale, with a total conversion of 92% across four synthesis steps. High purity was achieved with no further purification. The intermediates and compounds were characterized using attenuated total reflectance infrared spectroscopy, proton nuclear magnetic resonance, differential scanning calorimetry, thermogravimetric analysis, cyclic voltammetry, rotating disk electrode voltammetry, density, and viscosity measurements. The structural characterization verified the structure of 2,3,5,6-tetraallylbenzene-1,4-diol. Electrochemical characterization revealed a quasi-reversible response, a diffusion coefficient similar to the diffusion coefficient of hydroquinone.