Evidence map›Paper›PMID 29997807›Full record

ArticleChemical science2016

High yielding synthesis of 2,2'-bipyridine macrocycles, versatile intermediates in the synthesis of rotaxanes.

J E M Lewis, R J Bordoli, M Denis, C J Fletcher, M Galli, E A Neal, E M Rochette, S M Goldup

Erratum issuedAbstract read
In one paragraph

Article in Chemical science, 2016. 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 35 papers.

0numbers the graph read from it
0cells of the map it votes in
35citing 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

35 citing papers in PubMed.

  1. Article
  2. Article
  3. Organic Cage Rotaxanes.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025
    Article
  4. Strain-Controlled Synthesis of [Organic letters · 2025
    Article
  5. Synthesis of a Station-Less Molecular Daisy Chain.Chemistry (Weinheim an der Bergstrasse, Germany) · 2025
    Article
  6. Article
  7. The End of the Beginning of Mechanical Stereochemistry.Accounts of chemical research · 2024
    Article
  8. The Final Stereogenic Unit of [2]Rotaxanes: Type 2 Geometric Isomers.Journal of the American Chemical Society · 2024
    Article
  9. Article
  10. Direct Detection of Hydrogen Bonds in Supramolecular Systems UsingJournal of the American Chemical Society · 2022
    Article
  11. Article
  12. Article
  13. A Co-conformationally "Topologically" Chiral Catenane.Journal of the American Chemical Society · 2022
    Article
  14. Article
  15. Anion-π Catalysis Enabled by the Mechanical Bond.Angewandte Chemie (International ed. in English) · 2022
    Article
  16. Article
  17. Rotaxane CoAngewandte Chemie (International ed. in English) · 2021
    Article
  18. Article
  19. Article
  20. Article
4 · The record

Corrections and comments

5 · Who and what money

Authors and funding

8 authors.

J E M LewisChemistry , University of Southampton , Highfield , Southampton , SO17 1BJ , UK . Email: s.goldup@soton.ac.uk.
R J BordoliSchool of Biological and Chemical Sciences , Queen Mary University of London , Mile End Road , London , E1 4NS , UK.
M DenisChemistry , University of Southampton , Highfield , Southampton , SO17 1BJ , UK . Email: s.goldup@soton.ac.uk.
C J FletcherChemistry , University of Southampton , Highfield , Southampton , SO17 1BJ , UK . Email: s.goldup@soton.ac.uk.
M GalliChemistry , University of Southampton , Highfield , Southampton , SO17 1BJ , UK . Email: s.goldup@soton.ac.uk.
E A NealSchool of Biological and Chemical Sciences , Queen Mary University of London , Mile End Road , London , E1 4NS , UK.
E M RochetteChemistry , University of Southampton , Highfield , Southampton , SO17 1BJ , UK . Email: s.goldup@soton.ac.uk.
S M GoldupChemistry , University of Southampton , Highfield , Southampton , SO17 1BJ , UK . Email: s.goldup@soton.ac.uk.

Funding

No grant is acknowledged in the PubMed record.

6 · The paper itself

Abstract

We present an operationally simple approach to 2,2'-bipyridine macrocycles. Our method uses simple starting materials to produce these previously hard to access rotaxane precursors in remarkable yields (typically >65%) across a range of scales (0.1-5 mmol). All of the macrocycles reported are efficiently converted (>90%) to rotaxanes under AT-CuAAC conditions. With the requisite macrocycles finally available in sufficient quantities, we further demonstrate their long term utility through the first gram-scale synthesis of an AT-CuAAC [2]rotaxane and extend this powerful methodology to produce novel Sauvage-type molecular shuttles.

Identifiers

PMID29997807
PMCPMC6005271

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Registered trials

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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.