| Abstract: | Three optically active phenylacetylene polymers with chiral bulky pinanyl groups, (?)‐poly4‐(dimethylpinanylsilyl)phenylacetylene] (?)‐poly(PSPA)], (+)‐poly{4‐3‐(10‐pinanyl)tetramethyldisiloxy]phenylacethylene} (+)‐poly(PDSPA)], and their copolymer (?)‐copoly(PSPA/PDSPA)], were synthesized. We observed high chirality in the main‐chain chromophore of (?)‐poly(PSPA), due to the presence of a chiral helix, with circular dichroism spectroscopy. In contrast, (+)‐poly(PDSPA),with flexible SiOSi spacers between the chiral pinanyl group and the main chain, had lower chirality. (?)‐Poly(PSPA), with large circular dichroism signals, was prepared by polymerization with a rhodium catalyst and had a highly stereoregular main chain (high cis‐configuration percentage). However, (?)‐poly(PSPA) prepared with a tungsten catalyst had lower chirality and lower stereoregularity in the main chain. A membrane from (?)‐poly(PSPA) showed enantioselective permeability for tryptophan in an aqueous solution. © 2002 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 40: 1689–1697, 2002 |
