A [3 + 6] prismatic homochiral organic cage used as stationary phase for gas chromatography

• A [3 + 6] prismatic homochiral organic cage NC1-R was developed as stationary phase for GC with good separation performance. • Various racemates and organic isomers have been well separated on the NC1-R coated column. • The column exhibits prominent chiral recognition complementarity to commercial β-DEX 120 column. • Many racemates failed to be resolved on the commercial β-DEX 120 column but can be well resolved on the NC1-R coated column. • Good application prospects of NC1-R for GC separations. Porous organic cages (POCs) are a new class of advanced porous molecular materials, which are self-assembled from discrete, shape-persistent, cage-like molecules through relatively weak intermolecular forces. POCs have recently received extensive interest in diverse fields due to their noteworthy features of good solubility, unique pore structure, high stability, tunable pore size and volume, and so on. In this study, we report a [3 + 6] prismatic homochiral POC (NC1-R) as the stationary phase for preparing a capillary gas chromatographic (GC) column by a static coating method. Various types of mixtures have been well separated on the coated column, involving n -alkanes, n -alcohols, alkylbenzenes, positional isomers, structural isomers, and cis- / trans -isomers. Most importantly, the column also exhibits excellent chiral resolution capability for racemates. Twenty-three racemates, including alcohols, epoxides, esters, lactones, ethers, amino acid derivatives, amines, and sulfoxides, have been well resolved on the column. Among these racemates, about half (11 of the 23) could not be resolved on a commercial β-DEX 120 column (per- O -methylated β-cyclodextrin-based column), suggesting the advantageous performance of the present column. Furthermore, the fabricated column shows good reproducibility in terms of the retention times of analytes, with relative standard deviations (RSDs) in the ranges 0.02–0.19 %, 0.12–0.36 %, and 0.41–0.59 % for intra-day ( n = 6), inter-day ( n = 6), and column-to-column ( n = 3), respectively, and good thermal stability at least up to 300 °C. This work demonstrates the good application prospects of NC1-R for GC separations, especially for GC enantioseparations.