Investigation of pi-pi and ion-dipole interactions on 1-allyl-3-butylimidazolium ionic liquid-modified silica stationary phase in reversed-phase liquid chromatography.

1-Allyl-3-butylimidazolium bromide ionic liquid [AyBIm]Br was prepared and used for the modification of mercaptopropyl-functionalized silica through surface radical chain-transfer addition. The obtained ionic liquid-modified silica (SiImBr) was characterized by elemental analysis, infrared spectroscopy, NMR spectroscopy, and thermogravimetric analysis. The selective retention behaviours of polycyclic aromatic hydrocarbons (PAHs) including some positional isomers were investigated using SiImBr as a stationary phase in reversed-phase liquid chromatography. The results showed that SiImBr presented multiple interactions including hydrophobic, pi-pi, and ion-dipole interactions during the separation of PAHs and dipolar compounds. However, it is proposed that pi-pi and ion-dipole interactions play important roles in the separation of PAHs and dipolar compounds. These results indicate that the ionic liquid-modified silica stationary phase is promising for future applications. A commercially available monomeric octadecylated silica (ODS) column and a custom-made poly(styrene)-grafted silica (Sil-St(n)) column were used as references. Copyright 2010 Elsevier B.V. All rights reserved.