How do crown ethers allow inorganic salts to dissolve in nonpolar organic solvents?

Crown ethers enable inorganic salts to dissolve in nonpolar organic solvents by acting as size-selective cyclic molecules that encapsulate specific metal cations.12

The process works through the following mechanism:

• Complexation: The crown ether features a central cavity lined with ether oxygen atoms. A metal cation of the appropriate size fits into this cavity, where it is solvated by the oxygen atoms.12
• Masking: The exterior of the resulting crown-ether-cation complex is composed of the molecule's alkyl groups, which are nonpolar. This effectively masks the positive charge of the cation, making the entire complex compatible with nonpolar solvents.2
• Solubilization: As the crown ether pulls the cation into the nonpolar solvent, the associated anion is dragged along to maintain electrical neutrality. Because the anion remains largely unsolvated in the nonpolar environment, it often exhibits significantly higher reactivity as a "bare" ion compared to its state in polar solvents.2