Synthesis of Ferrocene−Cyclodextrin, Anthracene−Cyclodextrin, and Pyrene−Cyclodextrin Rotaxane Conjugates and Their Intercomponent Behavior as Observed in NMR Spectroscopy
Ferrocene, anthracene, and pyrene-terminated alkynylated moieties were reacted with azidized beta-cyclodextrin derivatives to form supramolecular structures under various conditions. While initial experiments concerning mono-azidized beta-cyclodextrin proved difficult to isolate and have limited solubility, their reaction with peracetylated mono-azidized beta-cyclodextrin was more facile. Introduction and threading of the macrocycle, dibenzo-24-crown-8 (DB24C8), allowed for rotaxane synthesis. These compounds were characterized by infrared spectroscopy (IR), nuclear magnetic resonance spectroscopy (NMR), and mass spectrometry (MS). Among the compounds formed, the ferrocene-capped species showed promising host-guest inclusion complexation with the cyclodextrin cavity.
Tumaneng, J.V., Matulac, A.L., Reyes, J., Baldovino, A.J., Lumba, J., & Yu, G. (2022). Synthesis of ferrocene−cyclodextrin, anthracene−cyclodextrin, and pyrene−cyclodextrin rotaxane conjugates and their intercomponent behavior as observed in NMR spectroscopy. Asian Journal of Organic Chemistry, 11(12), e202200541. https://doi.org/10.1002/ajoc.202200541