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A series of optically active poly(diphenylacetylene) derivatives bearing a chiral substituent (poly- 2  S ) or chiral and achiral substituents (poly-( 2  S  x - co - 3  1-x )) on all of their pendant phenyl rings were synthesized by the reaction of poly(bis(4-carboxyphenyl)acetylene) with ( S )-1-phenylethylamine (( S )- 2 ) or benzylamine ( 3 ) 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- 2  S and poly-( 2  S  x - co - 3  1-x ) (0.06 &lt; x &lt; 0.71) formed a preferred-handed helical conformation with opposite helical senses after thermal annealing despite possessing the same chiral pendant ( h -poly- 2  S and h -poly-( 2  S  x - co - 3  1-x )). Furthermore, h -poly- 2  S and h -poly-( 2  S  0.36 - co - 3  0.64 ) emitted circularly polarized luminescence with opposite signs. h -Poly- 2  S showed higher chiral recognition abilities toward a larger number of racemates than poly- 2  S 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. h -Poly-( 2  S  0.36 - co - 3  0.64 ) also exhibited good chiral recognition abilities toward several racemates, though the elution order of some enantiomers was reversed compared with h -poly- 2  S .

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