ArticleNature chemistry2015
Inducing and quantifying forbidden reactivity with single-molecule polymer mechanochemistry.
Article in Nature chemistry, 2015. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 40 papers.
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Who cites it
40 citing papers in PubMed.
- Force Reveals Hidden Conformations and Dissociation Pathways in Individual π-Interacting Dimers.Angewandte Chemie (International ed. in English) · 2026Article
- Modeling Targeted Mechanochemistry in Polymeric Solids.Chemical reviews · 2026Review
- Effect of hydrogen migration on the electronic structure of phenol derivatives observed by single-molecule conductance.Nature communications · 2025Article
- Force-induced transition state rupture enables mechanistic control in aziridine mechanochemistry.Chemical science · 2025Article
- Tuning the Ultimate Strain of Single and Double Network Gels Through Reactive Strand Extension.ACS central science · 2025Article
- Force-Triggered Thermodynamically Uphill Disulfide Reduction through Sulfur Oxidation State Control.Journal of the American Chemical Society · 2025Article
- Computational Exploration of Polymer Mechanochemistry: Quantitation of Activation Force and Systematic Discovery of Reaction Sites by the Extended Artificial Force-Induced Reaction Method.Journal of the American Chemical Society · 2025Article
- "Node" facilitated thermostable mechanophores for rapid self-strengthening in double network materials.Chemical science · 2025Article
- Mechanochemistry: Fundamental Principles and Applications.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2025Review
- Structure-property relationships for the force-triggered disrotatory ring-opening of cyclobutene.Chemical science · 2025Article
- The Role of Torsion on the Force-Coupled Reactivity of a Fluorenyl Naphthopyran Mechanophore.Journal of the American Chemical Society · 2025Article
- Advancing the Mechanosensitivity of Atropisomeric Diarylethene Mechanophores through a Lever-Arm Effect.Journal of the American Chemical Society · 2025Article
- Stereochemical Impacts on Acyclic Mechanochemical Carbon-Carbon Bond Activation.Angewandte Chemie (International ed. in English) · 2025Article
- Wedging crystals to fabricate crystalline framework nanosheets via mechanochemistry.Nature communications · 2024Article
- Review
- Furan Release via Force-Promoted Retro-[4+2][3+2] Cycloaddition.Journal of the American Chemical Society · 2023Article
- Naphthopyran molecular switches and their emergent mechanochemical reactivity.Chemical science · 2023Review
- Mechanochemically assisted morphing of shape shifting polymers.Chemical science · 2023Article
- Regio-controllable [2+2] benzannulation with two adjacent C(spScience (New York, N.Y.) · 2023Article
- Competitive Activation Experiments Reveal Significantly Different Mechanochemical Reactivity of Furan-Maleimide and Anthracene-Maleimide Mechanophores.ACS polymers Au · 2023Article
Corrections and comments
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Authors and funding
8 authors.
Funding
No grant is acknowledged in the PubMed record.
Abstract
Forbidden reactions, such as those that violate orbital symmetry effects as captured in the Woodward-Hoffmann rules, remain an ongoing challenge for experimental characterization, because when the competing allowed pathway is available the reactions are intrinsically difficult to trigger. Recent developments in covalent mechanochemistry have opened the door to activating otherwise inaccessible reactions. Here we report single-molecule force spectroscopy studies of three mechanically induced reactions along both their symmetry-allowed and symmetry-forbidden pathways, which enables us to quantify just how 'forbidden' each reaction is. To induce reactions on the ~0.1 s timescale of the experiments, the forbidden ring-opening reactions of benzocyclobutene, gem-difluorocyclopropane and gem-dichlorocyclopropane require approximately 130 pN less, 560 pN more and 1,000 pN more force, respectively, than their corresponding allowed analogues. The results provide the first experimental benchmarks for mechanically induced forbidden reactions, and in some cases suggest revisions to prior computational predictions.
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25803470What OpenQuestion holds
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.