Abstract
Three stereoisomers of Tröger's Base-based dimeric macrocycles Trögerophane 1 (T1) including one pair of enantiomers (rac-T1) and one meso isomer (R2NS2N-T1) were obtained and fully characterized by X-ray analysis. In the crystalline stacking state R2NS2N-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, R2NS2N-T1 and rac-T1 demonstrated different adsorption capacities toward the vapor of dichloromethane and acetone, respectively.
Highlights
Chirality is ubiquitous in the abundant forms of fundamental and crucial processes to create wellorder functional structures (Liu et al, 2015; Xing and Zhao, 2018) from natural chiral products amino acid, carbohydrate, nucleic acids, to biomacromolecules of proteins, DNA double helix, to macroscopic systems of chiral crystals, and even to the spiral nebulae of the macroscopic universe.Chiral self-sorting (Jedrzejewska and Szumna, 2017; Shang et al, 2018) is known as one of selfsorting (Safont-Sempere et al, 2011; Imai et al, 2019) behaviors, in which chirality is one of key differentiating factors for the selectivity of self-assembly
The obtained racemate crystals rac-Trögerophane 1 (T1) showed the heterochiral self-sorting along c axis with slipped ππ stacking interactions and the homochiral self-sorting along b axis forming supramolecular P/M helix by each single enantiomer, respectively
In the crystal of rac-T1, two enantiomers stacked via a slipped π-π interaction along c axis, and showed heterochiral self-sorting behaviors
Summary
Chirality is ubiquitous in the abundant forms of fundamental and crucial processes to create wellorder functional structures (Liu et al, 2015; Xing and Zhao, 2018) from natural chiral products amino acid, carbohydrate, nucleic acids, to biomacromolecules of proteins, DNA double helix, to macroscopic systems of chiral crystals, and even to the spiral nebulae of the macroscopic universe.Chiral self-sorting (Jedrzejewska and Szumna, 2017; Shang et al, 2018) is known as one of selfsorting (Safont-Sempere et al, 2011; Imai et al, 2019) behaviors, in which chirality is one of key differentiating factors for the selectivity of self-assembly. The obtained racemate crystals rac-T1 showed the heterochiral self-sorting along c axis with slipped ππ stacking interactions and the homochiral self-sorting along b axis forming supramolecular P/M helix by each single enantiomer, respectively. T1 meso isomer, R2N S2N -T1, showed heterochiral self-sorting behavior along a axis with cofacial ππ stacking interactions in crystal state, while homochiral selfsorting behavior was observed along b axis and supramolecular P/M helixes were formed T1 meso isomer itself is an achiral molecule.
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