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

Research output: Contribution to journal › Article

6 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)1260-1264
Number of pages5
JournalTalanta
Volume69
Issue number5
DOIs
Publication statusPublished - Jul 15 2006

Fingerprint

Halogenation
Silica Gel
Hydrocarbons
High Pressure Liquid Chromatography
Derivatives
Electrons
Porphyrins
Coulomb interactions
Benzene
Hydration
Methanol
Polarization
Static Electricity
porphine
n-hexane

Keywords

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

ASJC Scopus subject areas

  • Analytical Chemistry
  • Spectroscopy

Cite this

Effect of octabromination of a tetrakis(4-carboxyphenyl)porphine derivative bound to silica gels on HPLC retention behaviors of polyaromatic hydrocarbons. / Kitamura, Youji; Kawata, Kenji; Tanaka, Kurumi; Furuyashiki, Yuko; Mifune, Masaki; Tsukamoto, Ikuko; Saito, Madoka; Haginaka, Jun; Saito, Yutaka.

In: Talanta, Vol. 69, No. 5, 15.07.2006, p. 1260-1264.

Research output: Contribution to journal › Article

Kitamura, Y, Kawata, K, Tanaka, K, Furuyashiki, Y, Mifune, M, Tsukamoto, I, Saito, M, Haginaka, J & Saito, Y 2006, 'Effect of octabromination of a tetrakis(4-carboxyphenyl)porphine derivative bound to silica gels on HPLC retention behaviors of polyaromatic hydrocarbons', Talanta, vol. 69, no. 5, pp. 1260-1264. https://doi.org/10.1016/j.talanta.2005.12.049
Kitamura Y, Kawata K, Tanaka K, Furuyashiki Y, Mifune M, Tsukamoto I et al. Effect of octabromination of a tetrakis(4-carboxyphenyl)porphine derivative bound to silica gels on HPLC retention behaviors of polyaromatic hydrocarbons. Talanta. 2006 Jul 15;69(5):1260-1264. https://doi.org/10.1016/j.talanta.2005.12.049
Kitamura, Youji ; Kawata, Kenji ; Tanaka, Kurumi ; Furuyashiki, Yuko ; Mifune, Masaki ; Tsukamoto, Ikuko ; Saito, Madoka ; Haginaka, Jun ; Saito, Yutaka. / Effect of octabromination of a tetrakis(4-carboxyphenyl)porphine derivative bound to silica gels on HPLC retention behaviors of polyaromatic hydrocarbons. In: Talanta. 2006 ; Vol. 69, No. 5. pp. 1260-1264.
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AB - 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.

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