Highly Efficient Separation of BTEX via Amide Naphthotube Cavity-Confined Tandem C/N-H···π Interactions.

The separation of BTEX [benzene, toluene, ethylbenzene (EB), and xylene isomers] poses a huge challenge in the industry, attributed to their similar structures and physical properties. Supramolecular compounds show great promise for hydrocarbon separation. Herein, we designed two pairs of endo-functionalized amide naphthotubes with methyl and benzyl side chains, which were first employed as chromatographic separation materials and exhibited high shape-selectivity for BTEX. In particular, the amide naphthotubes with methyl side chains provided complete separation toward BTEX and anti-3a showed high selectivity for the p-xylene over other isomers with αPX/OX = 9.34, αPX/MX = 5.50, and αPX/EB = 4.30. The mechanism of BTEX separation originates from the synergistic effect of specially confined tandem N-H···π and C-H···π interactions toward aromatic compounds. The findings of this research show promise for practical applications in efficiently separating crucial aromatic isomers.