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. Host–guest complexation with nucleoside triphosphates in water has led to an achiral anthracene‐based tetracationic nanotube showing two levels of supramolecular chirality. This nanotube, which can adopt M‐ and P‐twisted conformations, exhibits adaptive chiral recognition with opposite CD spectra for ATP/GTP and CTP/UTP, and a strong excimer showing strong circularly polarized luminescence ((+)‐CPL; glum≈10−2) with ATP in water.