Litcius/Paper detail

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

Hao Nian, Lin Cheng, Ling Wang, Haiyang Zhang, Pinpin Wang, Yawen Li, Liping Cao

2021Angewandte Chemie15 citationsDOI

Abstract

Abstract 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, g lum ≈10 −2 ) in water.

Topics & Concepts

Chirality (physics)Supramolecular chemistrySupramolecular chiralityAnthraceneIntramolecular forceStereochemistryChemistryNanotubeCrystallographyIntermolecular forceMaterials sciencePhotochemistryNanotechnologyCrystal structureMoleculeOrganic chemistryPhysicsCarbon nanotubeQuarkQuantum mechanicsChiral symmetry breakingNambu–Jona-Lasinio modelSupramolecular Self-Assembly in MaterialsLuminescence and Fluorescent MaterialsSynthesis and Properties of Aromatic Compounds