Synthesis and polymerization of optically active N‐α‐methylbenzylmaleimide

Optically active N‐α‐methylbenzylmaleimide (MBZMI) was prepared with maleic anhydride and d‐(+)‐α‐methylbenzylamine. The polymerizations of MBZMI were carried out with α,α′‐azobisisobutyronitrile (AIBN) and n‐butyllithium (n‐BuLi) in tetrahydrofuran (THF). The specific rotations of the polymers obtained by AIBN and n‐BuLi initiator were +11.1° to +13.0° and −57.0° to −89.2°, respectively. The weight‐average molecular weights (Mw) for the polymers were between 4200 and 8000. Furthermore, MBZMI was copolymerized with styrene (ST) and methyl methacrylate (MMA) with AIBN in THF at 50°C to obtain optically active copolymers. The monomer reactivity ratios of MBZMI (M1) with ST (M2) were obtained as r1 = 0.027, r2 = 0.094 in the MBZMI–ST and r1 = 0.15, r2 = 1.54 in the MBZMI–MMA system. The Q‐e values for MBZMI were Q1 = 0.78, e1 = 1.62. All the polymers and copolymers were found to show a weakly negative circular dichroism (CD) peak at about 250 nm and a strongly positive CD peak at about 220 nm.