Preparation and characterization of polymer-based stationary phase modified with Thiacalix[4]arene

• Published in: BUNSEKI KAGAKU Vol. 53; no. 10; pp. 1073 - 1077
• Main Authors: HIRA, Natsuki, TANAKA, Nobuo, HOSOYA, Ken
• Format: Journal Article
• Language: Japanese
• Published: The Japan Society for Analytical Chemistry 01.10.2004
• Subjects: catechol; catecholamine; surface modified; Thiacalixarene; uniformly size polymer particle
• ISSN: 0525-1931
• DOI: 10.2116/bunsekikagaku.53.1073

We have prepared a polymer-based stationary phase modified with thiacalix[4]arene. 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, that consists of four p-tert-butylphenol-related groups cyclically connected through a single sulphur atom between each pair. It has a high-electron density area formed by hydroxyl groups and sulfur atoms. We studied the applicability of this interesting compound as a selector because of its specific feature for high-performance liquid chromatography (HPLC). First of all, uniformly sized polymer particles were prepared using ethylene glycol dimethacrylate (EDMA) as a cross-linker through a multi-step swelling and polymerization method. Methacrylic acid (MAA) was introduced onto the surface of polymer particles through an invented modification method. Thiacalix[4]arene was cavalently bonded to MAA using 1,4-dibromo-butane as a spacer to reduce any steric hindrance of MAA on the surface of the polymer particles. The prepared polymer-based stationary phase was evaluated with HPLC. It provided a specific chromatographic retention behavior only for catechol among positional isomers of xylene, cresol, and benzene-diol. Catecholamine showed a specific chromatographic retention behavior as catechol.