DOSY study on dynamic catenation: Self-assembly of a [3]catenane as a meta-stable compound from twelve simple components

Akiko Hori, Kazuhisa Kumazawa, Takahiro Kusukawa, Dillip Kumar Chand, Makoto Fujita, Shigeru Sakamoto, Kentaro Yamaguchi

Research output: Contribution to journalArticle

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Abstract

Synthesis of [2]catenane 6 has been successfully achieved by the combination of Pd complex 1 and pyridines 2 and 3 at a molar ratio of 2:1:1 in D2O. A mixture of square molecule 4 (prepared from 1 and 2) and macrocycle 5 (obtained from 1 and 3), in which the final ratio of 1, 2, and 3 was kept 2:1:1 reorganizes in D2O/CD3OD (1:1) to form 6 within one day. However, the same mixture in D2O shows the formation of novel [3]catenane 7 along with the [2]catenane. In order to make 7, the theoretical ratio of components 1, 2, and 3 should be 3:1:2. Thus, deliberately maintaining such ratio of the above-mentioned molecules, a higher proportion of the [3]catenane is observed in D2O as found from 1H NMR spectra of the system. Reorganization of the twelve components to form [3]catenane is supported by studies with the DOSY method. This method is a first attempt to separate, from a mixture, either catenanes or any other supramolecular self-assembly structures. CSI-MS studies further support the assigned catenane super structures 6 and 7. All the results indicate that the [2]catenane is thermodynamically the most stable structure, while the [3]catenane is a meta-stable self-assembly.

Original languageEnglish
Pages (from-to)4142-4149
Number of pages8
JournalChemistry - A European Journal
Volume7
Issue number19
DOIs
Publication statusPublished - 2001 Oct 1
Externally publishedYes

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Self assembly
Molecules
Pyridine
Nuclear magnetic resonance
Catenanes
Pyridines
catenane

Keywords

  • Catenanes
  • NMR spectroscopy
  • Palladium
  • Self-assembly
  • Supramolecular chemistry

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

DOSY study on dynamic catenation : Self-assembly of a [3]catenane as a meta-stable compound from twelve simple components. / Hori, Akiko; Kumazawa, Kazuhisa; Kusukawa, Takahiro; Chand, Dillip Kumar; Fujita, Makoto; Sakamoto, Shigeru; Yamaguchi, Kentaro.

In: Chemistry - A European Journal, Vol. 7, No. 19, 01.10.2001, p. 4142-4149.

Research output: Contribution to journalArticle

Hori, Akiko ; Kumazawa, Kazuhisa ; Kusukawa, Takahiro ; Chand, Dillip Kumar ; Fujita, Makoto ; Sakamoto, Shigeru ; Yamaguchi, Kentaro. / DOSY study on dynamic catenation : Self-assembly of a [3]catenane as a meta-stable compound from twelve simple components. In: Chemistry - A European Journal. 2001 ; Vol. 7, No. 19. pp. 4142-4149.
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