Dibenzofulvene (DBF) affords a polymer having pi-stacked conformation by anionic, cationic, and free-radical polymerization. In this study, DBF was polymerized anionically using potassium menthoxide as initiator to obtain optically active poly(DBF) having a chiral menthoxy group as a terminal group. The obtained polymer indicated circular dichroism (CD) absorption bands in the absorption wavelength range of fluorenyl group, indicating that chiral conformation was induced to the stacked main chain by the influence of the terminal group. The CD intensity was reversibly affected by temperature of measurement; hence, the chiral conformation may be rather dynamic. The effect of the terminal group was found to decrease as the chain length increased. Theoretical CD calculation indicated that the obtained polymer has a left-banded helical conformation and that the dihedral angle between neighboring monomeric units might be about 10-20 degrees. (c) 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 47: 239-246, 2009