Abstract
The glycoluril monomer is a popular building block in supramolecular chemistry as it is used for the synthesis of versatile host molecules which can interact with cationic, anionic or neutral guest molecules. Here we present the design and synthesis of a new hybrid macrocycle containing glycoluril and aromatic units. The reaction afforded a mixture of macrocyclic homologues from which a two-membered macrocycle was isolated as the main product. Two disastereomers of the macrocycle were separated and characterized by means of NMR spectroscopy and X-ray crystallography. Conformational changes of these diastereomers were investigated using DFT models and variable-temperature NMR.
Highlights
Macrocycles consisting of urea building blocks play an important role in supramolecular chemistry [1]
Bambus[6]urils are a special case of hemicucurbiturils, which comprise six glycoluril units connected by six methylene bridges within their structure [11,12]
The preparation of the macrocycles was based on a one-pot reaction of 2,4-dimethylglycoluril and m-xylylene dibromide, a structurally simple example of a chromophoric monomer (Scheme 1)
Summary
Macrocycles consisting of urea building blocks play an important role in supramolecular chemistry [1]. Both isomers 1a and 1b were present in the crude product due to the irreversible nature of the macrocyclization reaction. The preparation of the macrocycles was based on a one-pot reaction of 2,4-dimethylglycoluril and m-xylylene dibromide, a structurally simple example of a chromophoric monomer (Scheme 1).
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