Photo-Polymerization of Amphiphilic N,O-diacylated Serine-Based Monomers in their Micellar States for an Encapsulation

摘要

The photo-polymerization of amphiphilic monomers, two isomers of NO-diacylated serine (AM and EM), has been studied. Self-assembling properties of the monomers were characterized in aqueous media by NMR and fluorescence techniques. These data show that both can form micellar structures by forming hydrophobic cores from both of the polymerizable and alkyl groups. Photo-polymerizations of AAA and EM were performed in their micellar and solution states. In the micellar states, polymerizations proceeded rapidly and reached almost complete conversion within 1 h, while those in DMSO solutions did not. Comparing the polymers Obtained, we concluded that EM was more useful for further applications mainly because of the solubility of the resulting polymer. Based on DLS data, the resulting EM-polymer micelle had a diameter of ca. 20 nm, about ten times larger than the original micelle. Furthermore, preliminary experiments indicated that the micellar state polymerization of EM afforded an encapsulation of pyrene in a stable hydrophobic domain.