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

Račkauskaitė, Dovilė ; Gegevičius, Rokas ; Matsuo, Yutaka ; Wärnmark, Kenneth LU and Orentas, Edvinas (2016) In Angewandte Chemie (International edition) 55(1). p.208-212
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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author
; ; ; and
organization
publishing date
type
Contribution to journal
publication status
published
subject
in
Angewandte Chemie (International edition)
volume
55
issue
1
pages
208 - 212
publisher
John Wiley & Sons Inc.
external identifiers
  • pmid:26537418
  • wos:000368065300020
  • scopus:84955176638
  • pmid:26537418
ISSN
1521-3773
DOI
10.1002/anie.201508362
language
English
LU publication?
yes
id
c6b68a6a-b994-44e2-9fd9-5f15e07ab160 (old id 8243119)
date added to LUP
2016-04-01 10:38:23
date last changed
2025-10-14 13:19:04
@article{c6b68a6a-b994-44e2-9fd9-5f15e07ab160,
  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.}},
  author       = {{Račkauskaitė, Dovilė and Gegevičius, Rokas and Matsuo, Yutaka and Wärnmark, Kenneth and Orentas, Edvinas}},
  issn         = {{1521-3773}},
  language     = {{eng}},
  number       = {{1}},
  pages        = {{208--212}},
  publisher    = {{John Wiley & Sons Inc.}},
  series       = {{Angewandte Chemie (International edition)}},
  title        = {{An Enantiopure Hydrogen-Bonded Octameric Tube: Self-Sorting and Guest-Induced Rearrangement.}},
  url          = {{http://dx.doi.org/10.1002/anie.201508362}},
  doi          = {{10.1002/anie.201508362}},
  volume       = {{55}},
  year         = {{2016}},
}