title: An Enantiopure Hydrogen-Bonded Octameric Tube: Self-Sorting and Guest-Induced Rearrangement.
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.
authors.affiliation: Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius (Lithuania).
authors.forename: Dovilė
authors.initials: D
authors.lastname: Račkauskaitė
authors.affiliation: Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius (Lithuania).
authors.forename: Rokas
authors.initials: R
authors.lastname: Gegevičius
authors.affiliation: Department of Chemistry, School of Science, The University of Tokyo, 7-3-1 Hongo, Bunkyo-ku, Tokyo 113-0033 (Japan).
authors.forename: Yutaka
authors.initials: Y
authors.lastname: Matsuo
authors.affiliation: Center for Analysis and Synthesis, Department of Chemistry, Lund University, P.O. Box 124, 22100 Lund (Sweden).
authors.forename: Kenneth
authors.initials: K
authors.lastname: Wärnmark
authors.affiliation: Department of Organic Chemistry, Vilnius University, Naugarduko 24, 03225 Vilnius (Lithuania). edvinas.orentas@chf.vu.lt.
authors.forename: Edvinas
authors.initials: E
authors.lastname: Orentas
keywords: fullerenes; hydrogen bonds; inclusion compounds; self-sorting; supramolecular chemistry