Tartardiamide-Functionalized Chiral Organosilicas with Highly Ordered Mesoporous Structure

A novel chiral mesoporous organosilica with L-tartardiamide moieties integrated in the backbone has been synthesized for the first time by a mild synthetic approach with block copolymer P123 as a template. The materials have highly ordered 2D hexagonal mesostructure and uniform pore size in the range of 7.6 to 5.5 nm. NMR, IR, and TG analyses confirm that the tartardiamide group was successfully incorporated into the framework. The intrinsic chirality of L-tartardiamide endows the materials with unique optical activities and chiral-recognition properties. By dissolving the materials into NaOH, the solutions show rotation of polarized light by +8.42 degrees to +15.53 degrees, depending on the amount of the chiral moieties in the materials. Owing to the chirality of L-tartardiamide, the materials exhibited chiral-induction ability in the epoxidation of allyl alcohol, thus further demonstrating the chirality of the materials.