Tröger’s Base Based Triangular Macrocycles with a Nanoscale Cavity for Chirality-Dependent Packing in Single Crystals

In this Letter, two chiral triangular macrocycles based on Tröger's base scaffold were synthesized by a one-pot stereoselective Yamamoto coupling reaction. The stereoisomers were resolved by chiral HPLC and they showed persistent chiroptical properties. X-ray crystallographic analysis revealed that the molecules of one of the stereoisomers, (S,R,R)-MC, were packed into a two-dimensional planar supramolecular organic framework via multiple π···π stacking, [C–H···N], and [C–H···π] interactions between the Tröger's base scaffolds. On the other hand, the 1:1 racemic mixture, (S,R,R)-MC and (R,S,S)-MC, displayed a one-dimensional polymer chain-like packing structure.