Publication details

Xylylene-Glycoluril Macrocycles

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Year of publication 2018
Type Appeared in Conference without Proceedings
MU Faculty or unit

Faculty of Science

Description Glycoluril is a urea-based heterocyclic molecule, which is a suitable building block for macrocyclic receptors like cucuribiturils1 and bambusurils2. Bambusurils are potent anion receptors that were used to detect and quantify anions in a complex mixture by NMR3. In order to allow anion sensing by UV-VIS spectroscopy, we designed a new bambusuril derivative incorporating aromatic groups in its structure. Here we report preparation of xylylene-glycoluril macrocycles. Inspired by work of prof. Shimizu on aromatic-urea macrocycles4, we employed basic synthetic conditions instead of the acid catalyzed condensation usually used for bambusuril synthesis. It afforded us with macrocycles of various sizes (Figure 1), which were separated by reverse-phase flash chromatography. The conformational behavior of separated isomers of two-membered macrocycles were studied by temperature dependent NMR. The three-membered macrocycle was observed in a gas phase to bind anions.
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