An investigation on the impact of halidization on substituted dimethoxybenzenes

Kowalski, Jeffrey A.; Carney, Thomas J.; Huang, Jinhua; Zhang, Lu; Brushett, Fikile R.

doi:10.1016/j.electacta.2019.135580

Title: An investigation on the impact of halidization on substituted dimethoxybenzenes

Journal Article · 26 December 2019 · Electrochimica Acta

DOI: https://doi.org/10.1016/j.electacta.2019.135580 · OSTI ID:1755217

Kowalski, Jeffrey A. ^[1]; Carney, Thomas J. ^[1]; Huang, Jinhua ^[2]; Zhang, Lu ^[2]; Brushett, Fikile R. ^[1]

Massachusetts Inst. of Technology (MIT), Cambridge, MA (United States)
Argonne National Lab. (ANL), Argonne, IL (United States)

Functionalized organic molecules are emerging as charge storage materials in electrochemical technologies as the breadth and diversity of the organic design space offers the possibility of purpose-built materials with property sets optimized for a particular application. First developed as overcharge protection materials in lithium-ion batteries, substituted dialkoxybenzenes represent a potentially promising molecular platform for advancing soluble charge storage materials. In this study, we systematically substitute a series of halide groups at the 2- and 5-positions of the 1,4-dimethoxybenzene core, investigate the impact the halide groups have on molecular properties using electrochemical and spectroscopy methods, and compare these results to those of 2,5-dimethyl-1,4-dimethoxybenzene (25DDB), a previously reported derivative. In general, we observe that introduction of heavy halogen atoms leads to decreased gravimetric capacity as compared to 25DDB, but concomitantly improves solubility and redox potentials. As the halide functional group increases in size, the active material becomes less stable in its oxidized state as evinced by both cyclic voltammetry and bulk electrolysis cycling. None of the halogenated species are as stable as 25DDB indicating that these materials may be better suited for applications with more rapid cycling conditions (e.g., redox shuttling). More broadly, these results may serve as a useful data set for computational methods for materials discovery and optimization.

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Research Organization:: Argonne National Laboratory (ANL), Argonne, IL (United States)

Sponsoring Organization:: USDOE Office of Science (SC), Basic Energy Sciences (BES)

Grant/Contract Number:: AC02-06CH11357

OSTI ID:: 1755217

Journal Information:: Electrochimica Acta, Journal Name: Electrochimica Acta Vol. 335; ISSN 0013-4686

Publisher:: ElsevierCopyright Statement

Country of Publication:: United States

Language:: English

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37 INORGANIC, ORGANIC, PHYSICAL, AND ANALYTICAL CHEMISTRY
electroactive organic
halidization
high potential
molecular engineering

Title: An investigation on the impact of halidization on substituted dimethoxybenzenes

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