Ullmann coupling of benzyl ether protected 4-iodophenol with 4-nitrophenylazo aniline followed by deprotection in trifluoroacetic acid affords novel 4-(4-nitrophenylazo)-N,N-bis(4-hydroxyphenyl)aniline. Co-condensation of this azo bisphenol and 9,9'-bis(4-hydroxyphenyl)fluorene (BHPF) with phosgene gave high molecular weight polycarbonate with T-g = 239 degreesC and high thermal stability. The polymer was soluble in common organic solvents and high quality films were prepared and subjected to poling and electro-optic (EO) analysis. The copolymer exhibited a r(33) value of 3.7 pm/V. Synthesis, characterization, and thermal properties are described. (C) 2003 Elsevier Ltd. All rights reserved.