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- Title
Chromatographic molecular recognition for catechol-related compounds using thiacalix[4]arene as an effective selector.
- Authors
Hosoya, Ken; Hira, Natsuki; Watabe, Yoshiyuki; Tanaka, Nobuo; Kubo, Takuya; Kaya, Kunimitsu
- Abstract
Thiacalix[4]arene (5,11,17,23-tetra-tert-butyl-25,26,27,28-tetrahydroxy-2,8,14,20-tetrathiacalix[4]arene) is an amphiphilic molecule comprising fourp-tert-butylphenol-like groupsortho-linked by single sulfur atoms. This molecule has a high electron density area owing to the close proximity of the hydroxyl groups and sulfur atoms. We studied the applicability of this interesting compound as a selector for high-performance liquid chromatography (HPLC) thereby presumably exploiting this feature. Firstly, uniformly sized polymer particles were prepared by using a multi-step swelling and polymerization method with ethylene glycol dimethacrylate (EDMA) as a cross-linker. Methacrylic acid (MAA) was introduced onto the surface of the resulting polymer particles through a new modification method. Thiacalix[4]arene was chemically bonded through the MAA group by using 1,4-dibromobutane as a spacer to reduce steric hindrance around the MAA and the polymer particle itself. The performance of the prepared polymer-based thiacalix[4]arene-modified stationary phase was evaluated with HPLC. Specific chromatographic retention behavior was observed for catechol relative to positional isomers of xylene, cresol, and benzene-diol. Catecholamine and catechol showed specific chromatographic retention behavior.
- Subjects
SULFUR; ELECTRON distribution; HYDROXYL group; HIGH performance liquid chromatography; POLYMERIZATION; GLYCOLS; METHACRYLIC acid
- Publication
Analytical & Bioanalytical Chemistry, 2004, Vol 380, Issue 2, p343
- ISSN
1618-2642
- Publication type
Article
- DOI
10.1007/s00216-004-2705-z