Synthesis and Characterization of Ordered Poly(amide−ester)s from Isophthaloyl Chloride and 4-(2-Aminoethyl)phenol

The ordered [head-to-head (H−H) or tail-to-tail (T−T)] poly(amide−ester) was prepared by polycondensation of a symmetric monomer, isophthaloyl chloride (1), with 4-(2-aminoethyl)phenol (2) as a nonsymmetric monomer. The polymerization was conducted in NMP in the presence of triethylamine (TEA) at −20 °C by slow addition of 1 to 2, giving the ordered H−H or T−T poly(amide−ester) with an inherent viscosity of 0.27 dL/g, measured at a concentration of 0.5 g/dL at 30 °C in NMP. The authentic H−H or T−T, H−T ordered and random poly(amide−ester)s were prepared to verify the structure of ordered polymers. The microstructure of polymers obtained was investigated by 1 H and 13 C NMR spectroscopy, and it was found that the polymer obtained by polycondensation had the expected H−H or T−T ordered structure. Furthermore, the model reactions were studied in detail to demonstrate the feasibility of polymer formation. The constitutional regularity of polymers influenced the solubility, thermal properties, and crystallinity.