Xylylene-Glycoluril Macrocycles

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Authors

LÍZAL Tomáš ŠINDELÁŘ Vladimír

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

Faculty of Science

Citation
Description Bambusurils1 are potent anion receptors that are synthetized by acidic condensation of 2,4-disubstituted glycolurils and formaldehyde. They were used to detect and quantify anions in a complex mixture by NMR2. 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 macrocycles3, we employed basic synthetic conditions instead of the acid catalyzed condensation. It afforded us with macrocycles of various sizes (Fig. 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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