Thermoresponsive chiral stationary phase functionalized with the copolymer of β-cyclodextrin and N-isopropylacrylamide for high performance liquid chromatography.

A novel chiral stationary phase (CSP) was prepared through the reaction of surface-initiated atom transfer radical polymerization (ATRP) by the copolymerization of thermoresponsive N-isopropylacrylamide (NIPAM) and β-cyclodextrin (β-CD) on the silica beads for high performance liquid chromatography (HPLC). X-ray photoelectron spectroscopy (XPS), elemental analysis (EA), Fourier transform infrared spectrometry (FT-IR), thermogravimetric analysis (TGA) and scanning electron microscopy (SEM) were applied to characterize the surface property of modified silica. Thermoresponsive modulation for the effect on enantioselectivity were investigated with chiral reagents including 1-phenyl-1-propanol, styrene oxide, 2-phenylpropionic acid and commercial chiral drugs comprising ibuprofen and labetalol hydrochloride. The column efficiency was evaluated by chromatographic parameters including retention factor (k), selective factor (α), resolution (R), plate number (N) and peak tailing factor (T). The results showed that five chiral solutes could be separated on the prepared smart column. And the selectivity of these compounds could be modulated by regulating the column temperature. It was contributed to the thermoresponsive NIPAM assisting β-CD to separate these chiral compounds. These results indicated that the thermoresponsive CSP would be a potential tool for separation of hydrophilic and hydrophobic chiral drugs and this paper provided a novel method for chiral separation in the future.