Ferulic acid (FA), a bio-based resource found in cereals, fruits and vegetables, and a hydroxyl-amino acid, have been used to develop a new class of poly(carbonate-amide)s which possess the potential to degrade into natural products under hydrolytic or enzymatic conditions. L-Serine was first envisaged as partner for FA to generate the diol necessary for the condensation polymerization. Unfortunately, the p-�nitrophenyl carbonate synthesized led systematically to the elimination product. Consequently, the strategy was revised and L-tyrosine ethyl ester, which lacks an acidic proton on the a-position of the ethyl ester, was used. To determine the microstructure importance into the polymer properties, we decided to generate the three regioselective poly(carbonate-amide)s possible: head-to-tail, head-to-head and tail-to-tail. Two AB monomers, activated as p�nitrophenyl carbonate and chloroformate, were necessary to reach the high regioselectivity expected for a head-to-tail polymer, whereas the synthesis of the dimer and its polymerization in presence of diphosgene gave access to the head-to-head and tail-to-tail sequences. A more effective way to reach the desired polymer was developed via the straightforward synthesis of a regiorandom poly(carbonate-amide) in only two steps from commercially-available reagents. Moreover, fluorescent studies revealed interesting photophysical properties for the monomers and their corresponding poly(carbonate-amide)s, making these materials potentially viable for sensing and/or imaging applications, in addition to their attractiveness as engineering materials derived from renewable resources. 

Poly(ferulic acid-co-tyrosine), a poly(carbonate-amide) derived from bio-based resources:  Synthesis and characterization

248th National Meeting (2014)

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