AUTHOR=Chen Yuan , Cheng Ming , Hong Benkun , Zhao Qian , Qian Cheng , Jiang Juli , Li Shuhua , Lin Chen , Wang Leyong 

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

JOURNAL=Frontiers in Chemistry

VOLUME=7

YEAR=2019

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2019.00383

DOI=10.3389/fchem.2019.00383

ISSN=2296-2646

ABSTRACT=<p>Three stereoisomers of Tröger's Base-based dimeric macrocycles Trögerophane <bold>1</bold> (<bold>T1</bold>) including one pair of enantiomers (<bold><italic>rac</italic>-T1</bold>) and one meso isomer (<bold><italic>R</italic></bold><sub>2<italic>N</italic></sub><bold><italic>S</italic></bold><sub>2<italic>N</italic></sub><bold>-T1</bold>) were obtained and fully characterized by X-ray analysis. In the crystalline stacking state <bold><italic>R</italic></bold><sub>2<italic>N</italic></sub><bold><italic>S</italic></bold><sub>2<italic>N</italic></sub><bold>-T1</bold> showed heterochiral self-sorting behavior along <italic>a</italic> axis with cofacial π<italic>-</italic>π stacking interactions, while <bold><italic>rac</italic>-T1</bold> showed heterochiral self-sorting behavior along <italic>c</italic> axis with slipped π-π stacking interactions, respectively. Meanwhile both of them showed homochiral self-sorting behavior along <italic>b</italic> 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 <italic>N</italic>-centered chiral superstructures is a rare example. In addition, <bold><italic>R</italic></bold><sub>2<italic>N</italic></sub><bold><italic>S</italic></bold><sub>2<italic>N</italic></sub><bold>-T1</bold> and <bold><italic>rac</italic>-T1</bold> demonstrated different adsorption capacities toward the vapor of dichloromethane and acetone, respectively.</p>