Abstract
A new exo-fructofuranoid monomer 5 was synthesized through a four-step reaction. This unsaturated sugar monomer has been successfully tested in radical polymerization. Homo- and copolymerizations were carried out in solution under various conditions. The corresponding saccharide polymers were isolated as white powder and well characterized. Polymer compositions were determined by elemental analysis (C, H, N) and 1H and 13C NMR. Polymerization parameters were determined for the binary system 1,2,3,4-tetra-O-benzoyl-6-deoxy-α-D-threo-5-eno-hexofuranose-2-uloside (5)/MA giving the reactivity ratios r1 = 0.47 for 5 and r2 = 1.13 for MA. The thermal behaviour of saccharide polymers was investigated showing a linear relationship between the glass transition temperature (Tg) of the saccharide polymers and the sugar content. The saccharide polymers also showed optical activity and exhibit negative optical rotation. Both Tg and the specific optical rotations ([α]20D) increase with increasing sugar content.
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