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Synthesis and chromatographic evaluation of a new stationary phase based on mild thiol-Michael addition reaction.

Journal of chromatography. A (2020-01-01)
Ruting Xiao, Aijin Shen, Gaowa Jin, Wenyi Yu, Zhimou Guo, Jing Zeng
ABSTRACT

Click chemistry has attracted increasing attention for the synthesis of novel stationary phases. Considering the advantage of click chemistry, a strategy based on thiol-Michael addition was developed for the preparation of a new stationary phase herein, and a phenyl vinyl sulfone stationary phase (M-PVS) was prepared. The resulting M-PVS bonded silica was characterized by elemental analysis, solid-state 13C cross-polarization/magic-angle spinning NMR and infrared spectroscopy, confirming the successful immobilization of phenyl vinyl sulfone on the silica support. The retention properties of M-PVS were investigated and exhibited unambiguous reversed phase retention characteristics. Moreover, shape selectivity and silanol activity were studied to reveal the diverse interactions of M-PVS, including hydrophobic, π-π, hydrogen bonding, and ion-exchange interactions. In addition, de-wetting tolerance and hydrophilic properties were evaluated and a pronounced "U" retention curves were obtained, indicating enhanced retention for polar analytes and transitions of different interaction modes. Selectivity differences between M-PVS column, phenyl column and conventional C18 column were examined using series natural standards. The diverse interactions of M-PVS demonstrated its improved selectivity for the compounds with similar hydrophobic skeleton but different polar substituents.

MATERIALS
Product Number
Brand
Product Description

Sigma-Aldrich
1,3-Propylene sulfite, 99%
Sigma-Aldrich
Dimethylphenylphosphine, 99%
Sigma-Aldrich
Phenyl vinyl sulfone, 99%