Poly (azo-ester)s: Interfacial Synthesis of Optically Active Polymers

(2S)-5-(3-Methyl-2-phthalimidylpentanoylamino)isophthalic acid (1), (2S)-5-(2-Phthalimidiylpropanoylamino) isophthalic acid, and (2S)-5-(3-phenyl-2-phthalimidylpropanoylamino)isophthalic acid were prepared from phthalic anhydride, 5-aminoisophthalic acid and the corresponding L-amino acids in acetic acid. The interfacial polycondensation of the corresponding diacid chlorides with two aromatic diazo containing diols such as 4,4’-[4,4’-diphenyl sulfonedi-diazene- 2,1-diyl] bis (phenol) and 4,4’-[4,4’-diphenyl etherdi-diazene-2,1-diyl] bis(phenol) were carried out at room temperature. Six novel optically active poly (azo-ester)s (PAE)s including phthalimide groups were obtained with good yields and inherent viscosities of 0.12-0.25 dLg-1. The new (PAE)s are readily soluble in organic solvents. The resulting polymers were characterized by specific rotation, FT-IR and 1H NMR spectroscopy, elemental analysis and thermo gravimetric analysis (TGA).