cis-9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboxylic acid anhydride (1) was converted to imide acid (2) by reaction with S-valine. Compound 2 was converted to the acid chloride (3) by reaction with thionyl chloride and then treated with 5-aminoisophthalic acid in dry N,N-dimethylacetamide to obtain 5-[(9,10-dihydro-9,10-ethanoanthracene-11,12-dicarboximido)-3-methylbuta noylamino]isophthalic acid (4). Direct step-growth polymerization of this novel chiral diacid monomer 4 with a series of different diols in a system of tosyl chloride, pyridine, and N,N-dimethylformamide was carried out. The optically active polyesters (PEs) were obtained with good yield and moderate inherent viscosity ranging from 0.23 to 0.48 dL/g. The resulting polymers were characterized with FTIR, H-1-NMR, and elemental analysis techniques. The prepared PEs showed good thermal stability up to 320 degrees C as measured by thermogravimetric analysis. Specific rotation experiments demonstrated the induction of optical activity due to successful insertion of S-valine in the structure of pendant groups. (C) 2010 Wiley Periodicals, Inc. J Appl Polym Sci 1:17: 3239-3246, 2010