Radical Polymerization Behavior of a Proline-Substituted Acrylamide. Effect of s-Cis−s-Trans Isomerization on the Polymerization

Synthesis and radical polymerization of a proline-substituted acrylamide, N -methacryloyl- l -proline methyl ester (A-P-M) were carried out. The isomerization of A-P-M between s- cis and s- trans forms of A-P-M was analyzed by 1 H NMR spectroscopy and molecular dynamics simulation, and the effect of the cis − trans isomerization on the radical polymerization of A-P-M was examined. The content of s- cis form of A-P-M increased with the NMR measuring temperature. The radical polymerization of A-P-M at higher temperature afforded the polymer with a higher s- cis content and a lower absolute value of specific rotation. It was suggested that the s- cis /s- trans ratio and the tacticity of the polymer affected the optical properties.