N-Centered Chiral Self-Sorting and Supramolecular Helix of Tröger's Base-Based Dimeric Macrocycles in Crystalline State

Three stereoisomers of Tröger's Base-based dimeric macrocycles Trögerophane 1 (T1) including one pair of enantiomers (rac-T1) and one meso isomer (R(2N)S(2N)-T1) were obtained and fully characterized by X-ray analysis. In the crystalline stacking state R(2N)S(2N)-T1 showed heterochiral self-sorting behavior along a axis with cofacial π-π stacking interactions, while rac-T1 showed heterochiral self-sorting behavior along c axis with slipped π-π stacking interactions, respectively. Meanwhile both of them showed homochiral self-sorting behavior along b axis as well as one pair of supramolecular helixes were formed in both cases. All the self-sorting behaviors are controlled by two chiral Tröger's Base units from neighboring molecules. To the best of our knowledge, such chiral self-sorting and supramolecular helixes of N-centered chiral superstructures is a rare example. In addition, R(2N)S(2N)-T1 and rac-T1 demonstrated different adsorption capacities toward the vapor of dichloromethane and acetone, respectively.