# Ureas are identified as the first neutral O-donors broadly effective in stabilizing ionic liquids and other salts of boron-centred cations: synthesis and detailed characterization

## TL;DR

Ureas help stabilize boronium ions, expanding their use in ionic liquids with unique properties like H-bond donation.

## Contribution

Ureas are shown to be effective neutral O-donors for stabilizing boronium cations, enabling new structural and functional possibilities.

## Key findings

- Ureas combined with amines stabilize boronium cations, broadening their structural diversity.
- Urea-stabilized boronium ionic liquids act as effective H-bond donors despite being aprotic.
- These materials resist de-ionization in the presence of bases, unlike protic ionic liquids.

## Abstract

Stimulated by recent work showing them to be promising electrolytes in batteries and supercapacitors, and to have useful levels of antibacterial, antifungal, and antiviral activity, there is growing interest in salts of boron-centered cations – boronium ions. However, compared to the number of existing structural variants among molecular cations such as ammonium ions, that of boroniums is minescule. This likely stems from the narrow scope of Lewis base types – largely amines and N-heterocycles – known to stabilize cationic boron centres. We have now determined that ureas, in combination with amines, are effective in stabilizing boronium cations, greatly enhancing the scope of structural-geometric space which can be explored with these compounds. And, depending on the specific urea utilized, ionic liquids based upon the new boroniums are effective H-bond donors despite being ‘aprotic’ ILs in nature. The new materials have been assessed by a broad array of techniques, including TGA, DSC, CV, NMR, and X-ray crystallography.

Urea-stabilized boronium ions are good H-bond donors. They also can have multiple, orientationally flexible H-bond donor sites in a single cation. Unlike protic ILs, the boroniums are not subject to ready de-ionization in the presence of bases.