Novel chiral poly(ester-imide)s with different natural amino acids in the main chain as well as in the side chain: synthesis and characterization

Abstract

Several novel chiral and potentially biodegradable poly(ester-imide)s (PEI)s bearing natural amino acids in the main chain as well as in the side chain were synthesized via direct polyesterification of N,N'-(pyromellitoyl)-bis-(L-tyrosine dimethyl ester) as a biodegradable optically active phenolic diol and synthesized diacids containing different amino acids and phthalimide group in the side chain. With the aim of tosyl chloride/pyridine/N,N-dimethylformamide (DMF) system as a condensing agent under conventional heating condition, the new optically active PEIs were obtained in good yield and moderate inherent viscosity up to 0.35 dL/g. The obtained polymers were characterized with FT-IR, 1H NMR, X-ray diffraction (XRD), elemental and thermogravimetric analysis (TGA) techniques. They are readily soluble in amide type solvents such as N,N-dimethylacetamide, DMF, 1-methyl-2-pyrrolidone, dimethyl sulfoxide, and protic solvents such as sulfuric acid. TGA showed that the 10% weight loss temperature in argon atmosphere was around 350 °C, which indicates that the resulting PEIs have a good thermal stability. The presence of amino acid in the PEIs architecture, not only cause to be used as optically active materials but also makes them susceptible to be biocompatible and biodegradable compound.