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Effect of octabromination of a tetrakis(4-carboxyphenyl)porphine derivative bound to silica gels on HPLC retention behaviors of polyaromatic hydrocarbons |
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| Authors: | Kitamura Youji Kawata Kenji Tanaka Kurumi Furuyashiki Yuko Mifune Masaki Tsukamoto Ikuko Saito Madoka Haginaka Jun Saito Yutaka |
| Affiliation: | aDepartment of Pharmaceutical Sciences, Graduate School of Medicine and Dentistry and Pharmaceutical Sciences, Okayama University, Tsushima-Naka, Okayama 700-8530, Japan bDepartment of Pharmaceutical Chemistry, Graduate School of Natural Science and Technology, Okayama University, Tsushima-Naka, Okayama 700-8530, Japan cFaculty of Medicine, Kagawa University, Ikenobe, Miki-Cho, Kagawa 761-0793, Japan dFaculty of Pharmaceutical Sciences, Mukogawa Women's University, Koshien, Nishinomiya 663-8179, Japan |
| Abstract: | The effect of bromination of Cu-porphyrin-derivative-immobilized silica gels (Cu-TCPPD) was examined by comparing the retention behaviors of polyaromatic hydrocarbons (PAHs) on Cu-TCPPD and Cu-octabromotetrakis(4-carboxyphenyl)porphine-derivative-immobilized silica gels (Cu-OBTCPPD) columns. It was revealed that bromination affects strongly the π–π electron interactions caused from hydration energy in a polar eluent (80% methanol) possibly as a result of a destruction of planar structure of porphine-ring by bromination. It was also revealed that bromination enhances π–d interactions as well as the π–π electron interactions in a broad sense (e.g., dispersion forces) in a non-polar eluent (n-hexane). However, the bromination did not exert much influence on electrostatic interactions caused from polarization of mono-halogenated benzenes. |
| Keywords: | HPLC stationary phase π–d Interaction π–π Interaction Bromination of porphyrin Dispersion force Polyaromatic hydrocarbons |
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