Synthesis And Characterization Of Water-Soluble Poly (N-propargylamides)

Substituted polyacetylenes are drawing growing attention especially after the 2000 Chemistry Nobel prize was awarded to Professor Shirakawa, et al. These versatile polymers possess some interesting properties e.g. electric conductivity, optical property, magnetic property, etc. Another intriguing feature is that some substituted polyacetylenes can adopt helical structures under appropriate conditions. This has become one the research hot topics in the two decades.However, it is known that most poly(N-propargylamides) were hydrophobic, limiting the application investigations of the polymers. For this reason, two novel glycol-polyacetylenes were designed and synthesized in this thesis. Poly(N-propargylamides) with water-soluble pendent groups (δ-gluconolactone and lactobionic acid) were designed and synthesized. Due to the existence of 8-gluconolactone and lactobionolactone groups in side chains, the polymers would be improved in their wate-solubility, biological compatibility, and degradation.N-Propargylgluconicamide and N-propargyllactobionicamide were synthesized with N-propargylamide andδ-gluconolactone and lactobionic acid respectively and were characterized by IR and NMR measurements. The water-soluble N-propargylgluconicamide and N-propargyllactobionicamide were polymerized in aqueous media in the presence of hydrophilic Rh catalyst. The resulting polymers were characterized with IR, ~1HNMR, GPC and CD analyses. In addition, this thesis studied the effects of polymerization temperature, time, and solvent on polymerizations, providing some fundermental understanding of the polymerization of water-soluble substituted acetylenes. Results showed that the molecular weights of polymers were 10000-15000, and they were not formed helical structures.