ArticleJournal of the American Chemical Society2021
High-Yielding Flow Synthesis of a Macrocyclic Molecular Hinge.
Article in Journal of the American Chemical Society, 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 9 papers.
What it found
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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.
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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.
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Who cites it
9 citing papers in PubMed.
- Enabling technology for accelerated discovery of supramolecular materials.Chemical science · 2025Review
- Conservation of structure and dynamic behavior in triazine macrocycles with opportunities for subtle control of hinge motion.Organic & biomolecular chemistry · 2025Article
- Biomimetic Entropy-Dominant Molecular Hinges with Picomolar Affinity.Journal of the American Chemical Society · 2024Article
- Scrolling in Supramolecular Gels: A Designer's Guide.Chemistry of materials : a publication of the American Chemical Society · 2024Article
- Queer in Chem: Q&A with Professor Anna G. Slater.Communications chemistry · 2023Article
- Thermally Stable Photomechanical Molecular Hinge: Sterically Hindered Stiff-Stilbene Photoswitch Mechanically Isomerizes.JACS Au · 2023Article
- Controlling Swing Rates in Macrocyclic Molecular Mortise Hinges.Chemistry (Weinheim an der Bergstrasse, Germany) · 2023Article
- Quid Pro Flow.Journal of the American Chemical Society · 2023Review
- Enabling Technology for Supramolecular Chemistry.Frontiers in chemistry · 2021Review
Corrections and comments
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Authors and funding
6 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Many molecular machines are built from modular components with well-defined motile capabilities, such as axles and wheels. Hinges are particularly useful, as they provide the minimum flexibility needed for a simple and pronounced conformational change. Compounds with multiple stable conformers are common, but molecular hinges almost exclusively operate via dihedral rotations rather than truly hinge-like clamping mechanisms. An ideal molecular hinge would better reproduce the behavior of hinged devices, such as gates and tweezers, while remaining soluble, scalable, and synthetically versatile. Herein, we describe two isomeric macrocycles with clamp-like open and closed geometries, which crystallize as separate polymorphs but interconvert freely in solution. An unusual one-pot addition cyclization reaction was used to produce the macrocycles on a multigram scale from inexpensive reagents, without supramolecular templating or high-dilution conditions. Using mechanistic information from NMR kinetic studies and at-line mass spectrometry, we developed a semicontinuous flow synthesis with maximum conversions of 85-93% and over 80% selectivity for a single isomer. The macrocycles feature voids that are sterically protected from guests, including reactive species such as fluoride ions, and could therefore serve as chemically inert hinges for adaptive supramolecular receptors and flexible porous materials.
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Registered trials
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.