A novel diacid isophthalic acid bis-(carboxyphenyl methyl) ester (IBE) containing optically active center and bulky pendent groups was successfully synthesized and used to prepare a series of aromatic polyesters. IBE was prepared via a reaction of R-()-mandelic acid with isophthaloyl chloride in the presence of potassium hydroxide. Direct polycondensation reactions of this monomer with various aromatic diols using para-toluenesulfonyl chloride (p-TsCl) via a Vilsmeier adduct resulted in the preparation of new optically active polyesters. Polyester showed reasonable molecular weight based on gel permeation chromatography (GPC) and inherent viscosity methods. Other physical and thermal properties of the polymers, including solubility, thermal behavior, thermal stability, and crystallinity in addition to optical activity, were studied. These heat-resistant polymers showed optical activity and presence of bulky groups improved their solubility. According to the X-ray diffraction patterns, the polyesters were almost amorphous. (C) 2011 Wiley Periodicals, Inc. Adv Polym Techn 31: 354363, 2012; View this article online at wileyonlinelibrary.com. DOI 10.1002/adv.20258