Abstract
AbstractA bis‐urea‐functionalized ditopic subcomponent assembled with 2‐formylpyridine and FeII, resulting in a dynamic library of metal–organic assemblies: an irregular FeII4L6 structure and three FeII2L3 stereoisomers: left‐ and right‐handed helicates and a meso‐structure. This library reconfigured in response to the addition of monosaccharide derivatives, which served as guests for specific library members, and the rate of saccharide mutarotation was also enhanced by the library. The (P) enantiomer of the FeII2L3 helical structure bound β‐D‐glucose selectively over α‐D‐glucose. As a consequence, the library collapsed into the (P)‐FeII2L3 helicate following glucose addition. The α‐D‐glucose was likewise transformed into the β‐D‐anomer during equilibration and binding. Thus, β‐D‐glucose and (P)‐3 amplified each other in the product mixture, as metal–organic and saccharide libraries geared together into a single equilibrating system.
Highlights
A bis-urea-functionalized ditopic subcomponent assembled with 2-formylpyridine and FeII, resulting in a dynamic library of metalorganic assemblies: an irregular FeII4L6 structure, and three FeII2L3 stereoisomers: left- and right-handed helicates and a meso-structure. This library reconfigured in response to the addition of monosaccharide derivatives, which served as guests for specific library members, and the rate of saccharide mutarotation was enhanced by the library
The library collapsed into the (P)-FeII2L3 helicate following glucose addition
Thirteen monosaccharide derivatives with different sizes and stereoconfigurations were employed for host-guest studies (Figure 3). 1H NMR spectra revealed evidence of binding to mesocate 2 and helicate 3 for nine of the monosaccharide derivatives (Figures 3a, S29-36)
Summary
A bis-urea-functionalized ditopic subcomponent assembled with 2-formylpyridine and FeII, resulting in a dynamic library of metalorganic assemblies: an irregular FeII4L6 structure, and three FeII2L3 stereoisomers: left- and right-handed helicates and a meso-structure. Thirteen monosaccharide derivatives with different sizes and stereoconfigurations were employed for host-guest studies (Figure 3).
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