Supercycloalkanes: dihydropyrazine-embedded macrocycles with flexible conformations resembling cycloalkanes.

ABSTRACT: Cycloalkanoid molecules are of fundamental interest due to their unique geometric structures and physical properties. However, studies on the molecular dynamics of these molecules tend to be difficult owing to labile conformations. Herein, we report a series of "supercycloalkanes", namely dihydropyrazine-embedded macrocycles, that show puckered structures imitating those of cyclobutane, cyclopentane and cyclohexane, as confirmed by crystal structures. ¹H NMR spectrum analyses and theoretical calculations reveal that the macrocycle containing four dihydropyrazine corners undergoes a ring-flapping process in solution, and the one with five dihydropyrazine corners involves a pseudorotation process. Photophysical results indicate that these macrocycles show donor (D)-acceptor (A)-ty

SUBMITTER: Qiu S 

PROVIDER: S-EPMC12498244 | biostudies-literature | 2025 Nov

REPOSITORIES: biostudies-literature