Adjustable Chiral Self-sorting and Self-discriminating Behaviour between Diamond-like Tröger’s Base-linked Cryptands

Two isomers of Troger’s Base-linked cryptands 5a and 5b were synthesized, and both of them have two chiral N-centers, exhibiting rare diamond-like scaffolds. Particularly, while growing from the solution of rac-5a, single enantiomer RNRN-5a was found in the crystal cell, revealing chiral self-sorting behaviour. However, while adding CF3COOH to protonate Troger’s base in the solution of rac-5a, two enantiomers were both formed in pairs in the crystal cell, exhibiting chiral self-discriminating behaviour.