A new 4-ferrocenylbenzoyl chloride-bonded stationary phase for high performance liquid chromatography.

A new 4-ferrocenylbenzoyl chloride-bonded stationary phase (Fc-SiO2) for high performance liquid chromatography (HPLC) was prepared using 3-aminopropyltriethoxysilane as coupling reagent. The structure of new material was characterized by infrared spectroscopy, elemental analysis and thermogravimetric analysis. The chromatographic performance and retention mechanism of the new stationary phase were evaluated in reversed-phase (RP) or normal-phase (NP) modes using different solute probes including polycyclic aromatic hydrocarbons (PAHs), mono-substituted benzenes, ferrocenyl derivatives, aromatic amines, pyrazine derivatives, drug intermediate pyrrole isomers and sulfonamides. The results showed that this Fc-SiO2 could provide various interactions for different solutes, such as hydrophobic, hydrogen bonding, π-π, dipole-dipole and charge-transfer interactions. The synergistic effects resulting from cyclopentadienyl (Cp) groups, aromatic ring and amido function in the new material improved the separation selectivity by multiple retention mechanisms. The retention behaviors of the analytes on Fc-SiO2 column were investigated with the assistance of quantum chemistry calculation results using DFT-B3LYP/STO-3G(*) base group.