A new type of stationary bonded phase for liquid chromatography with various functional groups bonded to diol-modified silica via ester bond was synthesized. The structures of the proposed stationary phases contain: alkyl chains (C10, C18), phenyl, and cholesterol groups. The structures of the synthesized materials were confirmed by different physico-chemical techniques such as elemental analysis, infrared spectroscopy (FTIR), ¹³C CP/MAS NMR and liquid chromatography under reversed phase conditions (RP) and with hydrophilic interaction liquid chromatography (HILIC). Depending on the type of functionalities bonded to the Diol-Ester, the stationary phases are capable of separating various groups of compounds in RP and HILC, even using pure water as a mobile phase.