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N-Centered Chiral Self-Sorting and Supramolecular Helix of Tröger's Base-Based Dimeric Macrocycles in Crystalline
Yuan Chen1, Ming Cheng1, Benkun Hong1
1Key Laboratory of Mesoscopic Chemistry of MOE, Jiangsu Key Laboratory of Advanced Organic Materials, School of Chemistry and Chemical Engineering, Nanjing University, Nanjing, China.
Abstract:
Three stereoisomers of Tröger's Base-based dimeric macrocycles Trögerophane 1 (T1) including one pair of enantiomers ( ) and one meso isomer ( 2 2 -T1) were obtained and fully characterized by X-ray analysis. In the crystalline stacking state 2 2 -T1 showed heterochiral self-sorting behavior along a axis with cofacial π-π stacking interactions, while 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, 2 2 -T1 and demonstrated different adsorption capacities toward the vapor of dichloromethane and acetone, respectively.