ArticleChemical science2015
Competitive formation of homocircuit [3]rotaxanes in synthetically useful yields in the bipyridine-mediated active template CuAAC reaction.
Article in Chemical science, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 14 papers.
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Who cites it
14 citing papers in PubMed, 61 citations in OpenAlex.
- Expanding the Chemical Space of Mechanically Interlocked Peptides (MIPs) via Rational Design and Metabolite Profiling.JACS Au · 2025Article
- Facial Selectivity in Mechanical Bond Formation: Axially Chiral Enantiomers and Geometric Isomers from a Simple Prochiral Macrocycle.Journal of the American Chemical Society · 2024Article
- Dynamic Metalloporphyrin-Based [2]Rotaxane Molecular Shuttles Stimulated by Neutral Lewis Base and Anion Coordination.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- AT-CuAAC Synthesis of Mechanically Interlocked Oligonucleotides.Journal of the American Chemical Society · 2020Article
- Rotaxane PtChemical science · 2020Article
- Stereoselective Synthesis of Mechanically Planar Chiral Rotaxanes.Angewandte Chemie (International ed. in English) · 2018Article
- Chelating Rotaxane Ligands as Fluorescent Sensors for Metal Ions.Angewandte Chemie (International ed. in English) · 2018Article
- A Fluorescent Ditopic Rotaxane Ion-Pair Host.Angewandte Chemie (International ed. in English) · 2018Article
- Efficient Multicomponent Active Template Synthesis of Catenanes.Journal of the American Chemical Society · 2018Article
- Porphyrinoid rotaxanes: building a mechanical picket fence.Chemical science · 2017Article
- Macrocyclic shape-persistency of cyclo[6]aramide results in enhanced multipoint recognition for the highly efficient template-directed synthesis of rotaxanes.Chemical science · 2017Article
- A Kinetic Self-Sorting Approach to Heterocircuit [3]Rotaxanes.Angewandte Chemie (International ed. in English) · 2016Article
- High yielding synthesis of 2,2'-bipyridine macrocycles, versatile intermediates in the synthesis of rotaxanes.Chemical science · 2016Article
- Active-Metal Template Synthesis of a Halogen-Bonding Rotaxane for Anion Recognition.Chemistry (Weinheim an der Bergstrasse, Germany) · 2015Article
Corrections and comments
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Authors and funding
2 authors at 2 institutions in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We recently identified competitive formation of doubly interlocked [3]rotaxanes as the origin of the non-linear variation in yield of [2]rotaxane with macrocycle size in the bipyridine-mediated AT-CuAAC reaction. Selection of reaction conditions gave [2]rotaxanes in essentially quantitative yield in all cases and hard to access doubly threaded [3]rotaxanes in up to 50% yield in a single, four component coupling. Based on the effect of macrocycle structure on the reaction outcome we propose a detailed mechanism of [3]rotaxane formation.
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