A Cylinder-Shaped Macrocycle Formed Via Friedel-Crafts Reaction

By performing Friedel-Crafts reaction with a mixture of 1,3,5-tri(furan-2-yl) benzene (TFB) and acetone, we successfully synthesized a cylinder-shaped macrocycle. The isolated yield of 36% is relatively high, considering that twelve C-C bonds are formed simultaneously. The structure of this macrocycle was confirmed using H-1 NMR spectroscopy, mass spectrometry and X-ray crystallography. This macrocycle is able to recognize a variety of cationic guests driven by cation-dipole and CH-pi interactions.