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An Enantiopure Hydrogen-Bonded Octameric Tube: Self-Sorting and Guest-Induced Rearrangement
Dovilė Račkauskaitė1, Rokas Gegevičius1, Yutaka Matsuo2
1Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius (Lithuania).
Abstract:
The assembly of a discrete hydrogen-bonded molecular tube from eight small identical monomers is reported. Tube assembly was accomplished by means of selective heterodimerization between isocytosine and ureidopyrimidinone hydrogen-bonding motifs embedded in an enantiopure bicyclic building block, leading to the selective formation of an octameric supramolecular tube. Upon introduction of a fullerene guest molecule, the octameric tube rearranges into a tetrameric inclusion complex and the hydrogen-bonding mode is switched. The dynamic behavior of the system is further explored in solvent- and guest-responsive self-sorting experiments.
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