A cylinder-shaped macrocycle formed via Friedel–Crafts reaction

Abstract

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 ¹H 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–π interactions.