Chiral HPLC separation with self-assembled organic stationary phase

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Chiral separation is still significant target in analytical chemistry and separation technology because each enantiomer provides absolutely different action in biosystems. HPLC with chiral stationary phase has been recognized as a facile method to perform it. However, there are few examples those were accomplished with a reversed phase-HPLC mode as the most convenient HPLC. This is due to no hydrophobicity difference in each enantiomer. Therefore, we focused on self-assembled systems to enhance microenvironmental effect in molecular recognition and applied these systems for functional organic stationary phases. Our research project clarified that (1)poly(octadecyl acrylate)-grafted silica showed distinct enhanced selectivity to recognize small difference in the molecular shape of polyaromatic hydrocarbons through disordered-to-ordered stale phase transition of the long-chain alkyl moieties, (2)the enhanced selectivity was brought about from multiple carbonyl-π interaction between the stationary phase and solutes, and (3)combination of this HPLC with diastereomerizing agents showed enhanced selectivity for the resultant diastereomers.