Twisted Allenyl-Pyridocyclophanes by Templated Cyclooligomerization: Chiral Cavities for Precision Molecular Recognition
Abstract
High Resolution Image Download MS PowerPoint Slide We report the palladium-catalyzed one-pot synthesis of enantiopure 20-, 30-, and 40-membered cyclophanes shaped by axially twisted allene units. Under Cs + -template, the two smaller macrocycles ( 2 and 3 ) are favored over the largest ( 4 ). X-ray studies reveal that rac - 2 assembles into homochiral helices that pack to form channels, while rac - 3 forms racemic dimers. These shape-persistent hosts, with unique chiral 3D cavities, undergo guest-induced conformational switching and (enantio)selectively bind diols and ammonium cations, including hydroxycarboxylic acids and α-hydroxyammoniums, as evidenced by diagnostic ECD shifts.
Fields of Study & Subjects
Synthesis and Properties of Aromatic Compounds
Supramolecular Chemistry and Complexes
Axial and Atropisomeric Chirality Synthesis
Publication details
- Journal / source
- JACS Au
- Publisher
- American Chemical Society (ACS)
- Volume
- 6
- Issue
- 1
- Pages
- 589–599
- Publication date
- 2 January 2026
- Language
- EN