Optical Activity And Stereoregularity Of Chiral Poly (Meth) Acrylamides

In this thesis, two methyl acrylamide monomers of N-(2-oxo-1-phenyl-2-(phenylamino)ethyl)methacrylamide and2-methacrylamido-4-methyl-N-phenylpentanamide were designedand synthesized. Poly[L-PMACMAM] and Poly[L-ACIEMAM] were obtained by radicalpolymerization. Monomers and Polymers were characterized by proton nuclear magneticresonance (1H NMR) and infrared spectroscopy (IR).The influence of polymerizationconditions on the polymer stereoregularity and optical activity was investigated. Thestereoregularity of the polymers was analyzed by carbon nuclear magnetic resonance (13CNMR).The optical activity of the polymers was analyzed by circular dichroism (CD) andoptical rotation analyzer.The monomer of L-PMACMAM which was made from L-phencyclidine wassynthesized by a two-step synthetic method. The Chiral polymer of Poly[L-PMACMAM] wasobtained by radical polymerization. The effects of monomer concentration, Lewis acid,solvent and temperature on the stereoregularity and optical activity of the polymers werestudied.The results show that Lewis acid can significantly influence the stereoregularity of thepolymers.The ability of increasing isotacticticity of the trifluoromethanesulfonate wasstronger than metal chlorides. Increasing Lewis acid concentration is beneficial for increasingthe isotacticity. The increase of the isotacticity improved the optical activity. The decreasingof monomer concentration and increasing the solvent polarity is beneficial for increasing thesyndiotacticity.The monomer of L-ACIEMAM was made from L-leucine, methacryoyl chloride andphenylamine. The obtained crude product was purified by column chromatography. TheChiral polymer of Poly[L-ACIEMAM] was obtained by radical polymerization. The effects ofmonomer concentration, Lewis acid, solvent on the stereoregularity and optical activity of thepolymers were studied. The chiral stationary phase (CSP) was prepared from the opticallyactive polymer of Poly[L-ACIEMAM] by coating. And the chiral separation ability wasinvestigated by high performance liquid chromatography (HPLC) in the mobile phase ofhexane/isopropanol equal to90/10(v/v). The separation factor was1.26and1.55.