Dynamic Covalent Platform for Chiroptically Tunable Figure-Eight Macrocycles from Preorganized Alkaloidal Scaffolds.

ABSTRACT: Chiral D ₂-symmetric figure-eight macrocycles with extended π-conjugated systems represent versatile scaffolds for developing advanced chiroptical materials. Here, we present a dynamic covalent platform that transforms a preorganized alkaloidal bispyrrolidinoindoline (BPI) scaffold into a series of chiroptically tunable figure-eight macrocycles through thermodynamically controlled imine formation. Strategic installation of aryl-ethynyl substituents precisely preorganized the BPI scaffold, enabling highly efficient macrocyclization (up to a 81% yield) under reversible imine-forming conditions. This modular approach allowed systematic assembly of diverse intercrossing chromophores, affording 44-90-membered macrocycles exhibiting predictable variations in both optical and ch

SUBMITTER: Murakami S 

PROVIDER: S-EPMC12933323 | biostudies-literature | 2026 Feb

REPOSITORIES: biostudies-literature