Synthesis of Chiral Periodic Mesoporous Silicas (ChiMO) of MCM-41 Type with Binaphthyl and Cyclohexadiyl Groups Incorporated in the Framework and Direct Measurement of Their Optical Activity

Abstract

A series of periodic mesoporous silicas of MCM-41 type containing varying amounts (5−50%) of chiral binaphthyl and cyclohexadiyl moieties occupying framework positions have been synthesized, and their characteristic MCM-41 features were observed by powder XRD and porosity measurements. The covalent bonding of the organics to the silicate framework was confirmed by 1H and 29Si MAS NMR experiments. Direct measurement of the optical activity demonstrates that the solids are able to rotate the angle of plane-polarized light. Also, a certain degree of chiral discrimination has been observed for the asymmetric enhancement of the binaphthyl fluorescence by adding enantiomerically pure 1,2-cyclohexadiamine.