New stationary phase for liquid chromatography with chemically bonded pinane ligand: synthesis and characterization by nuclear magnetic resonance and high-performance liquid chromatographic investigations

A new bicyclic phase for liquid chromatography was prepared by solution polymerization approaches. To introduce a C4 spacer the starting molecule 3-formylpinane was reduced to the alcohol followed by a substitution of the hydroxy group through a bromide. The obtained halide reacted with magnesium and allyl bromide to the 3-(but-3'-enyl)pinane which was hydrosilylated with trichlorosilane and finally immobilized to silica gels with different pore sizes using the technique of solution polymerization. To elucidate the structure of 3-(but-3'-enyl)pinane high-resolution two-dimensional nuclear magnetic resonance (NMR) spectra were carried out. The new phases were characterized, on the one hand by employing 13C and 29Si solid-state NMR spectroscopy and on the other hand, by separating a standard test mixture consisting of mainly monosubstituted aromatic compounds. The results achieved in chromatography were correlated with the information gained from 29Si CP/MAS NMR measurements.