Porous Organic Cages for Gas Chromatography Separations

compounds 13 and to separate both krypton/xenon mixtures and chiral alcohols. 14 Here, we show that CC3 can also be used as a chromatographic stationary phase by coating it inside a standard capillary column. We show that such columns can be used for the GC separation of a range of mixtures including aromatic compounds, racemic mixtures, and branched alkanes. Homochiral CC3-R was produced by a one-pot imine condensation of 1,3,5-triformylbenzene with (R,R)-1,2-cyclohexanediamine, catalyzed by trifluoroacetic acid (Scheme 1). CC3-R has tetrahedral symmetry and includes four windows that are large enough to be penetrated by small molecules such as gases, 10 iodine, 15 or common organic solvents. 16 In the solid state, CC3-R packs window-to-window, resulting in a 3-D interconnected pore structure that runs through the center of each cage. This leads to high levels of permanent microporosity in the crystals after desolvation, with apparent BrunauerEmmett-Teller surface areas (SABET) of up to 800 m 2 g −1 , depending on the level of crystallinity. 17 A distinguishing