Hierarchical Two‐Level Supramolecular Chirality of an Achiral Anthracene‐Based Tetracationic Nanotube in Water. Issue 28 (9th June 2021)

• Record Type: Journal Article
• Authors: Nian, Hao; Cheng, Lin; Wang, Ling; Zhang, Haiyang; Wang, Pinpin; Li, Yawen; Cao, Liping
• Is Part Of: Angewandte Chemie international edition. Volume 60:Issue 28(2021)
• Page Start: 15354
• Page End: 15358
• Publication Date: 2021-06-09
• Subjects: anthracene -- chirality -- host–guest complexes -- nucleoside triphosphates -- supramolecular chemistry; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.202105593
• Languages: English
• ISSNs: 1433-7851

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, glum ≈10 −2 ) in water. Abstract : 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.