Issue 47, 2023

Data science enabled discovery of a highly soluble 2,2′-bipyrimidine anolyte for application in a flow battery

Abstract

Development of non-aqueous redox flow batteries as a viable energy storage solution relies upon the identification of soluble charge carriers capable of storing large amounts of energy over extended time periods. A combination of metrics including number of electrons stored per molecule, redox potential, stability, and solubility of the charge carrier impact performance. In this context, we recently reported a 2,2′-bipyrimidine charge carrier that stores two electrons per molecule with reduction near −2.0 V vs. Fc/Fc+ and high stability. However, these first-generation derivatives showed a modest solubility of 0.17 M (0.34 M e). Seeking to improve solubility without sacrificing stability, we harnessed the synthetic modularity of this scaffold to design a library of sixteen candidates. Using computed molecular descriptors and a single node decision tree, we found that minimization of the solvent accessible surface area (SASA) can be used to predict derivatives with enhanced solubility. This parameter was used in combination with a heatmap describing stability to de-risk a virtual screen that ultimately identified a 2,2′-bipyrimidine with significantly increased solubility and good stability metrics in the reduced states. This molecule was paired with a cyclopropenium catholyte in a prototype all-organic redox flow battery, achieving a cell potential up to 3 V.

Graphical abstract: Data science enabled discovery of a highly soluble 2,2′-bipyrimidine anolyte for application in a flow battery

Supplementary files

Article information

Article type
Edge Article
Submitted
05 Aug. 2023
Accepted
01 Nov. 2023
First published
02 Nov. 2023
This article is Open Access

All publication charges for this article have been paid for by the Royal Society of Chemistry
Creative Commons BY license

Chem. Sci., 2023,14, 13734-13742

Data science enabled discovery of a highly soluble 2,2′-bipyrimidine anolyte for application in a flow battery

A. R. Pancoast, S. L. McCormack, S. Galinat, R. Walser-Kuntz, B. M. Jett, M. S. Sanford and M. S. Sigman, Chem. Sci., 2023, 14, 13734 DOI: 10.1039/D3SC04084D

This article is licensed under a Creative Commons Attribution 3.0 Unported Licence. You can use material from this article in other publications without requesting further permissions from the RSC, provided that the correct acknowledgement is given.

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