Investigation on Retention Mechanism of Reversed-Phase Liquid Chromatography Using Peropyrene-type Polycyclic Aromatic Hydrocarbons.

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Polycyclic aromatic hydrocarbons (PAHs) have carcinogenic and/or mutagenic properties and therefore, it has been required to have a good analytical method. Generally in PAHs separation with reversed-phase liquid chromatography, which is seemed to be the most powerful and useful way, chemically bonded octadecylsilica (ODS) phases have been used as the representative stationary phase because of their capability and availability. In this investigation, different functional ODS phases have been synthesized in the laboratory and evaluated in their chromatographic performance, especially focusing on their ability of molecular planarity recognition for PAHs relating with their functionality and the retention mechanism has been interpreted by the consideration of molecular-molecular interaction between PAHs molecules and the stationary phase, of which structures have been confirmed by solid-state NMR spectrometry. After careful examinations, we have succeeded to design and synthesize two different types of stationary phases. One of them is dicoronylene and the other is multidentate phenyl bonded phases. The former can be useful to enhance the retention of planar PAHs and the latter can retain non-planar molecules longer than planar counterparts. The performance of those phases have been confirmed by chromatographic measurements. As the results, the investigations can open the new dimension to design novel stationary phases with enhanced selectivity of the separation, in which the theory induced from the interpretation of molecular-molecular interaction which plays an important role in liquid chromatography is basically used.