l-Lysine-linked anthracenophane derived from thermodynamically controlled intermediates

We easily and simply synthesized l-lysine-linked anthracenophane from [2+2] macrocyclization between anthracene-9,10-dicarboxaldehyde and l-lysine methyl ester by thermodynamically controlled process. The structure was characterized by single crystal X-ray resolution and 1H NMR. Circular dichroism spectrum showed induced-CDs including exciton-coupled CD, suggesting that intramolecular anthracene moieties exist in chiral arrangement. The resultant anthracenophane can form a 1:1 complex with a silver(I) ion in its cavity via NH-metal coordination and cation–π interaction (Ka = 2.62 × 105 M−1).