NATIVE/DERIVATIZED CYCLOFRUCTAN 6 BOUND TO RESINS VIA “CLICK” CHEMISTRY AS STATIONARY PHASES FOR ACHIRAL/CHIRAL SEPARATIONS.

Resin bound cyclofructan 6 (CF6) based stationary phases were prepared by immobilizing functionalized 4-azido-β-cyclofructan 6 (or its derivatives) to chloromethyl modified styrene divinylbenzene (MCI GEL CSP50/P10 CMS) via a 1,2,3-triazole linker. The resin bound native CF6 stationary phase (CF6-CMS) appears to have potential in HILIC separations of different types of polar compounds. The isopropyl carbamate derivatized stationary phases (IP-CF6-CMS) can be used as pH stable chiral stationary phases (CSPs) in HPLC. Under the optimum mobile phase conditions, 37 different types of chiral compounds have been separated on the IP-CF6-CMS column. The optimum mobile phase containing acetonitrile/methanol/triethylamine/acetic acid 70/30/0.2/0.5 was utilized as the starting condition for enantiomeric separations on the IP-CF6-CMS column. Lowering the separation temperature also is beneficial for these separations. The selectivity for some analytes on the IP-CF6-CMS column is comparable with that on the silica gel based LARIHC-CF6 column. These results indicated that there is potential for using these less expensive, but stable, resin based cyclofructan columns for HILIC or chiral separations in process chemistry. Finally, using 1-(1-naphthyl)-ethylamine as the model analyte, the column demonstrated excellent stability and reproducibility. [ABSTRACT FROM PUBLISHER]