Random copolymers, an optically functionalized isocyanate containing disperse red 1 (DR1NCO) with a chiral isocyanate containing (s)-(-)-2-methylbutanol (MBI), were prepared by anionic polymerization in THF at -98 degreesC with Na-Naph as a two-directional initiator. As the contents of MBI in the copolymer increased, the optical rotation of the polymer was also increased. To study about the optical activity change with initiator systems, homo polymer of MBI was synthesized with one-directional and two-directional initiator. The difference of optical activity in both systems was investigated using Circular Dichroism (CD) spectroscopy and optical rotation.