Ferulic acid (FA), a bio-based resource
found in fruits and vegetables,
was coupled with a hydroxyl-amino acid to generate a new class of
monomers to afford poly(carbonate–amide)s with potential to
degrade into natural products. l-Serine was first selected
as the hydroxyl-amino partner for FA, from which the activated p-nitrophenyl carbonate monomer was synthesized. Unfortunately,
polymerizations were unsuccessful, and the elimination product was
systematically obtained. To avoid elimination, we revised our strategy
and used l-tyrosine ethyl ester, which lacks an acidic proton
on the α position of the ethyl ester. Four new monomers were
synthesized and converted into the corresponding poly(carbonate–amide)s
with specific regioselectivities. The polymers were fully characterized
through thermal and spectroscopic analyses. Preliminary fluorescent
studies revealed interesting photophysical properties for the monomers
and their corresponding poly(carbonate–amide)s, beyond the
fluorescence characteristics of l-tyrosine and FA, making
these materials potentially viable for sensing and/or imaging applications,
in addition to their attractiveness as engineering materials derived
from renewable resources.