trans-1,4-Cyclohexylene ring containing acid chloride monomers were incorporated into poly(arylene ether sulfone) (PAES) backbones to study their effect on mechanical and thermal properties. The trans-1,4-cyclohexylene ring containing acid chloride monomers were synthesized and characterized by NMR and high-resolution mass spectrum. trans-1,4-Cyclohexylene containing PAESs were synthesized from the acid chloride monomers and hydroxyl terminated polysulfone oligomers with a pseudo-interfacial method and a solution method. These PAESs, with trans-1,4-cyclohexylene ring containing ester linkages, were fully characterized by NMR, thermogravimetric analysis, differential scanning calorimetry (DSC), size exclusion chromatography, and dynamic mechanical analysis (DMA). The tensile properties were also evaluated. The polymers made with the pseudo-interfacial method had relatively low molecular weights when compared to the solution method where much higher molecular weight polymers were obtained. Crystallinity was promoted in the low molecular weight biphenol-based PAES samples with the pseudo-interfacial method. The crystallinity was confirmed by both the DSC and the wide angle X-ray diffraction results. The tensile test results of the high molecular weight polymers suggested that incorporation of the trans-1,4-cyclohexylene ring containing linkage slightly improved the ultimate elongations while maintaining the Young's moduli. The trans-1,4-cyclohexylene ring containing PAESs also showed higher sub-T(g) relaxations in DMA when compared with their terephthaloyl containing analog. (C) 2011 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 49: 4316-4324, 2011