Hierarchical Two-Level Supramolecular Chirality of an Achiral Anthracene-Based Tetracationic Nanotube in Water.

Herein, we report an achiral anthracene-based tetracationic nanotube (1⋅4Cl- ) that shows two levels of supramolecular chirality: namely, conformationally adaptive host-guest complexation with nucleoside triphosphates (e.g. ATP, GTP, CTP, and UTP) and twisted packing of the chiral host-guest complexes in water. Interestingly, achiral 1⋅4Cl- exhibits chiral recognition for ATP/GTP and CTP/UTP through structural transformation of its intramolecular M- and P-twisted conformation as the first level of supramolecular chirality, which leads to adaptive chirality with opposite CD responses. Furthermore, the formation of chiral M-1⋅4Cl- ⊃ATP can promote an intermolecular P-twisted dimeric packing of anthracene rings as the second level of supramolecular chirality to achieve assembled chirality with strong circularly polarized luminescence arising from the excimer ((+)-CPL, glum ≈10-2 ) in water.