Synthesis of Ferrocene−Cyclodextrin, Anthracene−Cyclodextrin, and Pyrene−Cyclodextrin [2]Rotaxane Conjugates and Their Intercomponent Behavior as Observed in NMR Spectroscopy

Abstract

AbstractFerrocene, 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 [2]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.