Xylylene-Glycoluril Macrocycles: A New Bambusuril Derivatives
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| Year of publication | 2018 |
| Type | Appeared in Conference without Proceedings |
| MU Faculty or unit | |
| Citation | |
| 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. They 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 used 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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