Optically active polymers derived from chiral 2-oxazoline. synthesis, characterization, and chiroptical properties

A new monomer (1S, 2S)-(+)-2-acetamido-1-phenyl-1, 3-propanediol (4) was synthesized via the hydrolysis of (4S, 5S)-(−)-4-hydroxymethyl-5-phenyl-2-oxazoline (2), obtained from (1S, 2S)-(+)-2-amino-1-phenyl-1, 3-propanediol (1) and ethyl orthoacetate. Optically active polyurethanes (PU) with reduced viscosity of 0.15 and 0.13 g dl⁻¹ were prepared by polyaddition reaction of the diol 4 with 4, 4′-diphenylmethane diisocyanate (MDI) and toluene-2, 4-diisocyanate (TDI), respectively. Optically active polyester was prepared by polycondensation reaction with isophthaloyl chloride. The chiroptical properties of these optically active monomers and polymers, in solution or film state, were investigated by circular dichroic spectra (CD).