Studies Related to the Alternating Copolymerization of Substituted Stilbenes
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A novel series of methyl substituted stilbenes were synthesized and copolymerized with maleic anhydride. A conversion-time study was undertaken to understand the methyl substituent effect on copolymerization rates. Methyl substituted stilbene-maleic anhydride copolymer compositions were determined by quantitative 13C 1D NMR. SEC measurements showed the weight average molecular weights of these copolymers vary from 3 000 to over 1 000 000 g/mol. No glass transition temperature or crystalline melting temperature was observed between 0 oC and 250 oC by DSC. TGA showed that these polymers have 5% weight loss around 290 oC.
Precursors to a polycation and a polyanion based on functionalized stilbenes and maleimides have been prepared: poly(di-t-butyl-(E)-4,4â -stilbenedicarboxylate-co- N-(4-(t-butoxycarbonyl)phenyl)maleimide) and poly(N,N,Nâ ,Nâ -tetraalkyl-4,4â -di- aminostilbenes-co-N-4-(Nâ ,Nâ -dimethylaminophenyl)-maleimide). These copolymer precursors were characterized by 1H NMR, SEC, TGA, and DSC. The 1H NMR spectrum indicated the rigidity of copolymer backbones. SEC measurements showed the weight average molecular weights of these copolymers vary from 5 000 to 11 700 g/mol. No glass transition temperature or crystalline melting temperature was observed between 0 oC and 175 oC by DSC for poly(di-t-butyl-(E)-4,4â -stilbenedicarboxylate-co-N-(4-(t-butoxy- carbonyl)phenyl)maleimide). TGA showed that this polymer has 5% weight loss around 210 oC and 26% weight loss on the first stage of decomposition which corresponds to elimination of t-butyl functional group in the copolymer.
The homopolymerization of EMS-III via free radical polymerization, anionic polymerization and cationic polymerization was attempted. However, no polymer was obtained from any of these polymerization methods. In anionic polymerization, the solution changed to red upon the addition of the initiator sec-bu-Li, indicating the successful addition of the sec-bu-Li to EMS-III. However, the initiated monomer did not propagate to form homopolymer.
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