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C-H···π interactions disrupt electrostatic interactions between non-aqueous electrolytes to increase solubility. | LitMetric

AI Article Synopsis

  • Grid-scale energy storage, like redox flow batteries, depends on the solubility of certain organic molecules, specifically redox-active pyridiniums, which are great for energy storage but struggle with solubility in non-aqueous solvents.
  • The study highlights that attractive interactions between C-H groups and π electrons from aromatic rings (termed C-H···π interactions) can significantly influence the solubility of N-substituted pyridinium salts in acetonitrile.
  • A key finding is that there’s a direct link between the number of these C-H···π interactions and the solubility of the pyridinium salts, showing that minor structural

Article Abstract

Grid-scale energy storage applications, such as redox flow batteries, rely on the solubility of redox-active organic molecules. Although redox-active pyridiniums exhibit exceptional persistence in multiple redox states at low potentials (desirable properties for energy storage applications), their solubility in non-aqueous media remains low, and few practical molecular design strategies exist to improve solubility. Here we convey the extent to which discrete, attractive interactions between C-H groups and π electrons of an aromatic ring (C-H···π interactions) can describe the solubility of N-substituted pyridinium salts in a non-aqueous solvent. We find a direct correlation between the number of C-H···π interactions for each pyridinium salt and its solubility in acetonitrile. The correlation presented in this work highlights a consequence of disrupting strong electrostatic interactions with weak dispersion interactions, showing how minimal structural change can dramatically impact pyridinium solubility.

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Source
http://dx.doi.org/10.1038/s41557-023-01291-1DOI Listing

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