Evidence map›Paper›PMID 36456691›Full record

ArticleNature chemistry2023

Dimeric and trimeric catenation of giant chiral [8 + 12] imine cubes driven by weak supramolecular interactions.

Bahiru Punja Benke, Tobias Kirschbaum, Jürgen Graf, Jürgen H Gross, Michael Mastalerz

Erratum issuedAbstract read
In one paragraph

Article in Nature chemistry, 2023. The graph could read no effect estimate from its abstract, so it casts no vote on the map. An erratum has been issued. Cited by 19 papers.

0numbers the graph read from it
0cells of the map it votes in
19citing papers in PubMed
–field-weighted citation impact
1 · What the graph read from it

What it found

Each row is one number read from the abstract, on the scale the paper reported it, with its interval. Left of the dashed line favours the treatment, right favours the comparator. Under each row is the sentence it came from. New to these charts? A ten-minute tutorial.

The abstract states no effect estimate the extractor could read, or names no intervention and outcome on the map, so this paper lights no cell and moves no belief. It is still indexed, cited and linked below.

2 · The registry

The trial behind it

Trials whose registry record cites this paper, or whose number appears in the abstract. A trial that started after this paper was published is citing it as background, not reporting it.

Neither the registry nor the abstract names a trial number. If this is a trial report, that itself is worth knowing.

3 · Its place in the literature

Who cites it

19 citing papers in PubMed.

  1. Article
  2. Journal of the American Chemical Society · 2026
    Article
  3. Article
  4. Article
  5. Emerging mechanically interlocked cages.Nature reviews. Chemistry · 2025
    Review
  6. Review
  7. Mechanical interlocking of metal organic cages.Communications chemistry · 2025
    Review
  8. Article
  9. Article
  10. Article
  11. Engineering a Surfactant Trap via Postassembly Modification of an Imine Cage.Chemistry of materials : a publication of the American Chemical Society · 2024
    Article
  12. Article
  13. Article
  14. Article
  15. Article
  16. Article
  17. Dynamic covalent synthesis.Chemical science · 2024
    Review
  18. Article
  19. Porous Organic Cages.Chemical reviews · 2023
    Review
4 · The record

Corrections and comments

5 · Who and what money

Authors and funding

5 authors.

Bahiru Punja BenkeOrganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Heidelberg, Germany.
Tobias KirschbaumOrganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Heidelberg, Germany.
Jürgen GrafOrganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Heidelberg, Germany.
Jürgen H GrossOrganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Heidelberg, Germany.ORCID http://orcid.org/0000-0003-0748-2535
Michael MastalerzOrganisch-Chemisches Institut, Ruprecht-Karls-Universität Heidelberg, Heidelberg, Germany. michael.mastalerz@oci.uni-heidelberg.de.ORCID http://orcid.org/0000-0003-3231-4816

Funding

Deutsche Forschungsgemeinschaft (German Research Foundation) INST 40/5751EC | EU Framework Programme for Research and Innovation H2020 | H2020 Priority Excellent Science | H2020 European Research Council (H2020 Excellent Science - European Research Council) 725765European Research Council 725765
6 · The paper itself

Abstract

Mechanically interlocked structures, such as catenanes and rotaxanes, are fascinating synthetic targets and some are used for molecular switches and machines. Today, the vast majority of catenated structures are built upon macrocycles and only a very few examples of three-dimensional shape-persistent organic cages forming such structures have been reported. However, the catenation in all these cases was based on a thermodynamically favoured π-π-stacking under certain reaction conditions. Here, we show that catenane formation can be induced by adding methoxy or thiomethyl groups to one of the precursors during the synthesis of chiral [8 + 12] imine cubes, giving dimeric and trimeric catenated organic cages. To elucidate the underlying driving forces, we reacted 11 differently 1,4-disubstituted terephthaldehydes with a chiral triamino tribenzotriquinacene under various conditions to study whether monomeric cages or catenated cage dimers are the preferred products. We find that catenation is mainly directed by weak interactions derived from the substituents rather than by π-stacking.

Identifiers

PMID36456691
PMCPMC9986109

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Read under generation 80e0d062 · epoch 390. Bibliography from PubMed, PubMed Central and OpenAlex; grants from NIH RePORTER; trial links from ClinicalTrials.gov; estimates, votes and beliefs from the OpenQuestion graph.