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.