Synthesis of Optically Active Poly(diphenylacetylene)s Using Polymer Reactions and an Evaluation of Their Chiral Recognition Abilities as Chiral Stationary Phases for HPLC.

A series of optically active poly(diphenylacetylene) derivatives bearing a chiral substituent (poly-) or chiral and achiral substituents (poly-(--)) on all of their pendant phenyl rings were synthesized by the reaction of poly(bis(4-carboxyphenyl)acetylene) with ()-1-phenylethylamine (()-) or benzylamine () in the presence of a condensing reagent. Their chiroptical properties and chiral recognition abilities as chiral stationary phases (CSPs) for high-performance liquid chromatography (HPLC) were investigated. Poly- and poly-(--) (0.06 < x < 0.71) formed a preferred-handed helical conformation with opposite helical senses after thermal annealing despite possessing the same chiral pendant (-poly- and -poly-(--)). Furthermore, -poly- and -poly-(--) emitted circularly polarized luminescence with opposite signs. -Poly- showed higher chiral recognition abilities toward a larger number of racemates than poly- without a preferred-handed helicity and the previously reported preferred-handed poly(diphenylacetylene) derivative bearing the same chiral substituent on half of its pendant phenyl rings. -Poly-(--) also exhibited good chiral recognition abilities toward several racemates, though the elution order of some enantiomers was reversed compared with -poly-.