ArticleJournal of the American Chemical Society2022
Transamidation-Driven Molecular Pumps.
Article in Journal of the American Chemical Society, 2022. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 15 papers.
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Who cites it
15 citing papers in PubMed, 52 citations in OpenAlex.
- Inverted metal-free active template synthesis of rotaxanes via axle‑mediated macrocyclization.Nature chemistry · 2026Article
- Successive Ring Expansion Strategies for the Synthesis of Macrocycles and Medium-Sized Rings.Chemical reviews · 2026Article
- Active Templating by Mechanochemistry.Organic letters · 2026Article
- Metal-Free Active Template: A Straightforward Route to 4-Aminopyridinium-Based Rotaxane Molecular Shuttles.Angewandte Chemie (International ed. in English) · 2026Article
- A Molecular Machine Directs the Synthesis of a Rotaxane.Angewandte Chemie (International ed. in English) · 2026Article
- Active Transport of Macrocycles into Micelles Using Molecular Pumps.Angewandte Chemie (International ed. in English) · 2025Article
- Programmable molecular dethreading towards tunable drug release.Nature communications · 2025Article
- Light-driven molecular pumps: entanglement of thermodynamic and kinetic effects in the photocontrolled threading-unthreading of pseudorotaxanes.Organic & biomolecular chemistry · 2025Article
- Crown Ether-Peptide Rotaxanes.Angewandte Chemie (International ed. in English) · 2025Article
- Autonomous Dynamic Control of Crown Ether Cargo Release from [2]Rotaxane Carriers in a Piperidine Oscillator.Journal of the American Chemical Society · 2025Article
- Structural Influence of the Chemical Fueling System on a Catalysis-Driven Rotary Molecular Motor.Journal of the American Chemical Society · 2025Article
- A Modular Strategy for the Synthesis of Macrocycles and Medium-Sized Rings via Cyclization/Ring Expansion Cascade Reactions.Journal of the American Chemical Society · 2024Article
- Stepwise Operation of a Molecular Rotary Motor Driven by an Appel Reaction.Journal of the American Chemical Society · 2024Article
- Switched "On" Transient Fluorescence Output from a Pulsed-Fuel Molecular Ratchet.Journal of the American Chemical Society · 2023Article
- Recent Advances in the Preparation of Delivery Systems for the Controlled Release of Scents.International journal of molecular sciences · 2023Review
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Authors and funding
5 authors at 1 institution in 1 country.
Funding
No grant is acknowledged in the PubMed record.
Abstract
We report a new class of synthetic molecular pumps that use a stepwise information ratchet mechanism to achieve the kinetic gating required to sequester their macrocyclic substrates from bulk solution. Threading occurs as a result of active template reactions between the pump terminus amine and an acyl electrophile, whereby the bond-forming reaction is accelerated through the cavity of a crown ether. Carboxylation of the resulting amide results in displacement of the ring to the collection region of the thread. Conversion of the carbamate to a phenolic ester provides an intermediate rotaxane suitable for further pumping cycles. In this way rings can be ratcheted onto a thread from one or both ends of appropriately designed molecular pumps. Each pumping cycle results in one additional ring being added to the thread per terminus acyl group. The absence of pseudorotaxane states ensures that no dethreading of intermediates occurs during the pump operation. This facilitates the loading of different macrocycles in any chosen sequence, illustrated by the pump-mediated synthesis of a [4]rotaxane containing three different macrocycles as a single sequence isomer. A [5]rotaxane synthesized using a dual-opening transamidation pump was structurally characterized by single-crystal X-ray diffraction, revealing a series of stabilizing CH···O interactions between the crown ethers and the polyethylene glycol catchment region of the thread.
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