Synthesis of Activated Ester Functional Polyesters through Light-Induced [4+4] Cycloaddition Polymerization

A combination of light-induced [4+4] cycloaddition polymerization and activated ester substitution reaction is demonstrated as a new method to obtain novel polymeric structures. Bis-anthracene functionalized compound involving perfluorophenyl ester moiety namely, bisanthracenyl-PFPE, is prepared by an esterification reaction, then polymerized under UV light irradiated at 365 nm. The resulting polymer is reacted with a variety of amine compounds namely allylamine, benzylamine, furfurylamine, and propargylamine, under mild conditions. Quantitative conversions of perfluorophenyl ester groups into the respective amide groups as well as the thermal behaviors of all polymers are revealed by using various spectroscopic measurements such as Fourier transform infrared spectroscopy (FT-IR), gel permeation chromatography, NMR, and differential scanning calorimetry. (Figure presented.).