An Enantiopure Hydrogen-Bonded Octameric Tube: Self-Sorting and Guest-Induced Rearrangement

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, le...

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Bibliographic Details
Published in:Angewandte Chemie 2016-01, Vol.128 (1), p.216-220
Main Authors: Račkauskaitė, Dovilė, Gegevičius, Rokas, Matsuo, Yutaka, Wärnmark, Kenneth, Orentas, Edvinas
Format: Article
Language:eng ; ger
Subjects:
Assembly
Chemical bonds
Chemistry
Dynamical systems
Dynamics
Einschlussverbindungen
Formations
Fullerene
Fullerenes
Hydrogen
Hydrogen bonding
Inclusion complexes
Monomers
Selbstsortierung
Supramolekulare Chemie
Tubes
Wasserstoffbrücken
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Summary: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. Sei mein Gast: Eine oktamere supramolekulare Röhre wurde mithilfe einer selektiven Heterodimerisierung zwischen den Wasserstoffbrücken‐Partnern Isocytosin und Ureidopyrimidinon aus identischen kleinen bicyclischen Bausteinen aufgebaut. Durch Behandlung mit C60 wird der Wasserstoffbrücken‐Modus so geändert, dass sich die Röhre in einen tetrameren Einschlusskomplex umlagert.
ISSN:0044-8249
1521-3757
DOI:10.1002/ange.201508362