Chromatographic molecular recognition for catechol-related compounds using thiacalix[4]arene as an effective selector.
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 four p-tert-butylphenol-like groups ortho-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.
Department of Polymer Science and Engineering, Kyoto Institute of Technology, Matsugasaki, Sakyo-ku, Kyoto, 606-8585 Japan. kenpc@kit.ac.jp
Ken
K
Hosoya
Natsuki
N
Hira
Yoshiyuki
Y
Watabe
Nobuo
N
Tanaka
Takuya
T
Kubo
Kunimitsu
K
Kaya
D002395:Catecholamines / Q000032:analysis / Q000737:chemistry; D002396:Catechols / Q000032:analysis* / Q000737:chemistry; D002846:Chromatography, Affinity; D002851:Chromatography, High Pressure Liquid / Q000379:methods; D010316:Particle Size; D010636:Phenols / Q000737:chemistry*; D011108:Polymers / Q000737:chemistry
D002395:Catecholamines; D002396:Catechols; D010636:Phenols; D011108:Polymers; C442852:p-tert-butylthiacalix(4)arene