New hydrogen-bonded liquid-crystalline poly(ester amide)s (PEA)s were obtained from 1,4-terephthaloyl[bis-(3-nitro-N-anthranilic acid)] (5) or 1,4-terephthaloyl[bis-(N-anthranilic acid)] (6), with or without nitro groups, respectively, through the separate condensation of each with hydroquinone or dihydroxynaphthalene. The dicarboxylic monomers were synthesized from 2-aminobenzoic acid. The phase behavior of the monomers and polymers were studied with differential scanning calorimetry, polarized light microscopy, and wide-angle X-ray diffraction methods. Monomer 5, containing nitro groups, exhibited a smectic liquid-crystalline phase, whereas the texture of monomer 6 without nitro groups appeared to be nematic. The PEAS containing nitro groups exhibited polymorphism (smectic and nematic), whereas those without nitro groups exhibited only one phase transition (a nematic threaded texture). The changes occurring in the phase behavior of the polymers were explained by the introduction of nitro groups. (C) 2004 Wiley Periodicals, Inc.