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An Enantiopure Hydrogen‐Bonded Octameric Tube: Self‐Sorting and Guest‐Induced Rearrangement
Author(s) -
Račkauskaitė Dovilė,
Gegevičius Rokas,
Matsuo Yutaka,
Wärnmark Kenneth,
Orentas Edvinas
Publication year - 2016
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201508362
Subject(s) - enantiopure drug , sorting , tube (container) , hydrogen , materials science , chemistry , crystallography , mathematics , catalysis , organic chemistry , composite material , enantioselective synthesis , algorithm
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.