A new stationary phase (TTCPSP) has been prepared by covalently bonding 1,3,5-triazine tetrad-aza cyclophanes (TTCP) onto silica gel using 3-aminopropyl triethoxysilane as the coupling reagent. The stationary phase developed in this way was characterized by IR spectroscopy, elemental analysis and thermogravimetric analysis. The chromatographic performance and retention mechanisms of the new stationary phase were validated and compared with octadecylsilyl (ODS) stationary phases using a variety of compounds including monosubstituted benzenes, polycyclic aromatic hydrocarbons (PAHs) and flavonoids. The results indicate that the 1,3,5-triazine tetrad-aza cyclophanes (TTCPSP) stationary phase addresses solutes with multiple interactions, such as hydrophobic, hydrogen bonding, pi-pi, and inclusion interactions. TTCPSP, which shows strong retention ability to compounds containing -OH, -NH2 or phenyl conjugate groups, is promising as a type of solid phase extraction sorbent.