Stilbene containing polymers are a group of interesting and versatile polymers. The pendent phenyl ring along the polymer backbone can impart unusual rigidity to the polymer backbone due to steric repulsion. By functionalizing stilbene, a variety of functional groups and ionic groups can be precisely placed along the polymer chain with tunable charge density. Therefore, stilbene containing polymers are potentially rod-like polyelectrolytes with controllable charges and charge density. They are the basis of a novel group of rigid synthetic polyelectrolytes and can be used for furthering our knowledge of rigid polyelectrolytes. 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 °C and 250 °C by DSC. TGA showed that these polymers have 5% weight loss around 290 °C. Precursors to a polycation and a polyanion based on functionalized stilbenes and maleimides have been prepared: poly(di-t-butyl-(E)-4,4′-stilbenedicarboxylate-co- N-(4-(t-butoxycarbonyl)phenyl)maleimide) and poly(N,N,Nâ ,Nâ -tetraalkyl-4,4′-di- aminostilbenes-co-N-4-(N′,N′-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 °C and 175 °C by DSC for poly(di-t-butyl-(E)-4,4′-stilbenedicarboxylate-co-N-(4-(t-butoxy- carbonyl)phenyl)maleimide). TGA showed that this polymer has 5% weight loss around 210 °C 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. / Master of Science