Effect of octabromination of a tetrakis(4-carboxyphenyl)porphine derivative bound to silica gels on HPLC retention behaviors of polyaromatic hydrocarbons

Youji Kitamura, Kenji Kawata, Kurumi Tanaka, Yuko Furuyashiki, Masaki Mifune, Ikuko Tsukamoto, Madoka Saito, Jun Haginaka, Yutaka Saito

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6 Citations (Scopus)


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.

Original languageEnglish
Pages (from-to)1260-1264
Number of pages5
Issue number5
Publication statusPublished - Jul 15 2006



  • π-π Interaction
  • π-d Interaction
  • Bromination of porphyrin
  • Dispersion force
  • HPLC stationary phase
  • Polyaromatic hydrocarbons

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy

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