| Institution: | 1. Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University Chikusa-ku, Nagoya, 464-8603 Japan;2. Department of Molecular and Macromolecular Chemistry, Graduate School of Engineering, Nagoya University Chikusa-ku, Nagoya, 464-8603 Japan
Contribution: Data curation (lead), Formal analysis (lead);3. Department of Human Studies, Faculty of Arts and Humanities, Shikoku Gakuin University Zentsuji, Kagawa, 765-8505 Japan |
| Abstract: | A series of poly(biarylylacetylene)s (PBAs) bearing axially-chiral (S)-and (R)-pyridyl-N-oxide residues with a methoxy, propoxy, or acetyloxy substituent at the 3-position of the biaryl units was synthesized. All the PBAs formed a preferred-handed helix, while the helical sense preference was varied depending on the substituents despite the same twist-sense of the biaryl units. Among them, the propoxy-bound helical PBA showed an exceptionally high chiral recognition ability as a chiral stationary phase (CSP) for high-performance liquid chromatography (HPLC) and efficiently resolved not only various chiral aromatic alcohols, but also a variety of chiral aliphatic alcohols; the latter still remains difficult to resolve by commercially-available CSPs in HPLC. Such practically-useful both handed helical PBA-based CSPs can be produced from the racemic PBA composed of fully racemic monomer units through deracemization of the biaryl units with a chiral alcohol. |
