Aminopropyl silica gels were modified with two porphyrin derivatives and five phthalocyanine derivatives. The modified silica gels were evaluated for the usefulness as high-performance liquid chromatography stationary phases for the separation of π-electron-rich polyaromatic hydrocarbons (PAHs) such as naphthalene and phenanthrene. As a result of the modification, the aminopropyl silica gels acquired a function of π-π electron interaction with PAHs. In particular, the aminopropyl silica gel modified with copper phthalocyanine (Cu-PCS) showed the strongest π-π electron interaction with PAHs. It was the most suited as a stationary phase for the separations of PAHs among the modified silica gels tested. The Cu-PCS column could be utilized for the separation of π-electron-rich compounds including medicines, mutagens, and pollutants.
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