Aza-Michael addition allows reaction of nucleobase with 1,4-butanediol diacrylate to prepare nucleobase acrylate monomers. Copolymerization of cytosine acrylate with n-butyl acrylate produces poly (cytosine acrylate-co-n butyl acrylate) (poly (CyA-co-nBA)) random copolymers. Post-functionalization of poly (CyA-co-nBA) using isocyanate affords corresponding ureido-cytosine copolymer poly (UCyA-co-nBA). In this study, three pairs of random copolymers with different CyA and UCyA contents (3.4, 5.8, and 10.1 mol%, respectively) were synthesized for structural and property characterization. Thermogravimetric analysis (TGA) revealed a two-step weight loss of polymers, with UCyA polymers exhibited T5% weight loss at lower temperatures than CyA. Moreover, incorporation of nucleobase contents increased the polymers' glass transition temperature (Tg), and UCyA polymers showed higher Tg s than their CyA controls. Rheology analysis demonstrated a better thermomechanical performance of UCyA polymers, reflecting as an extended rubbery plateau due to the physical crosslinking provided by self-complementary hydrogen bonding. Morphological study of those polymers will offer further evidence of how hydrogen bonding affects the polymer’s self-assembly behavior.

Structure-property relationships of ureido-cytosine and cytosine-containing copolymers

254th National Meeting (2017)

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