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

Von Wiley-VCH zur Verfügung gestellt

Copper(I)-catalyzed azide-alkyne cycloaddition “click” reaction (CuAAC) has been utilized in the formation of [2]rotaxanes and other supramolecular structures. Six new cyclodextrin-terminated compounds are tested for possible host-guest inclusion complexation as investigated via 1D and 2D NMR spectroscopy.


Abstract

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 [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.

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