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

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93 Citations (Scopus)


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
Issue number19
Publication statusPublished - 2001 Oct 1
Externally publishedYes


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

ASJC Scopus subject areas

  • Catalysis
  • Organic Chemistry


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