Immobilization of Optically Active Helical Polyacetylene-Derived Nanoparticles on Graphene Oxide by Chemical Bonds and Their Use in Enantioselective Crystallization
The present study originally created a methodology for immobilizing polymeric nanoparticles on graphene oxide (GO) by chemical bonds, aiming at chiral functionalization of GO and simultaneously improving the dispersibility of polymer nanoparticles. To prepare the novel GO hybrids, GO was first prepared and alkynylated to form an actual comonomer (MGO), in the presence of which acetylenic monomer (M1) underwent emulsion polymerization in aqueous media with sodium dodecyl sulfate as emulsifier and (nbd)Rh+B–(C6H5)4 as catalyst. SEM and HRTEM images ascertained the formation of polymeric nanoparticles immobilized on GO (NPpoly1/GO). CD and UV–vis absorption spectra demonstrated the optical activity of NPpoly1/GO, originated from the chiral helical conformations adopted by the polymer chains constructing the nanoparticles. FT-IR, Raman, XPS, XRD, and TGA techniques were also utilized to characterize the GO hybrids. The as-obtained NPpoly1/GO was further used as a chiral additive to perform enantioselective crystallization of l-alanine from racemic alanine. l-Alanine was preferentially induced to crystallize rod-like crystals, according to SEM, CD, and XRD characterizations. The present study provides a versatile platform for preparing GO-derived functional materials, particularly novel chiral materials.
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