A series of immobilized bipyridine-proline based on mesoporous silica with different structures were synthesized via grafting followed by coordination method. All catalysts were used in asymmetric aldol reaction of cyclohexanone with 4-nitrobenzaldehyde, and their catalytic performance including activities and stabilities have been investigated. The results indicated that the pore structure, morphology, and even the particle dispersity all showed the effects on the catalytic performance of immobilized catalysts. [GRAPHICS] .