Buckybowl and its chiral hybrids featuring eight-membered rings and helicene units.

ABSTRACT: Here we report the synthesis of a novel buckybowl (7) with a high bowl-to-bowl inversion barrier (ΔG^‡ = 38 kcal mol^-1), which renders the rate of inversion slow enough at room temperature to establish two chiral polycyclic aromatic hydrocarbons (PAHs). By strategic fusion of eight-membered rings to the rim of 7, the chiral hybrids 8 and 9 are synthesized and display helicity and positive and negative curvature, allowing the enantiomers to be configurationally stable and their chiroptical properties are thoroughly examined. Computational and experimental studies reveal the enantiomerization mechanisms for the chiral hybrids and demonstrate that the eight-membered ring strongly affects the conformational stability. Because of its static and doubly curved conforma

SUBMITTER: Duan Y 

PROVIDER: S-EPMC10548505 | biostudies-literature | 2023 Oct

REPOSITORIES: biostudies-literature