ArticleAngewandte Chemie (International ed. in English)2021
Promoting the Furan Ring-Opening Reaction to Access New Donor-Acceptor Stenhouse Adducts with Hexafluoroisopropanol.
Article in Angewandte Chemie (International ed. in English), 2021. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 18 papers.
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Who cites it
18 citing papers in PubMed.
- Hexafluoroisopropanol Mediated Ring-Opening Reactions of Epoxides with Indoles Under Catalyst-Free Conditions.Molecules (Basel, Switzerland) · 2026Article
- Stenhouse Zwitterion Photoswitches as Hydrogen-Bond Acceptors.Journal of the American Chemical Society · 2026Article
- Photogated two conductive pathways of donor-acceptor Stenhouse adducts in single-molecule junctions.Nature communications · 2026Article
- Selective Green Colorimetric Liquid- and Solid-Based Determination of Furfural in Power Transformer Insulating Fluid.ACS omega · 2025Article
- Compartmentalizing Donor-Acceptor Stenhouse Adducts for Structure-Property Relationship Analysis.Journal of the American Chemical Society · 2025Review
- Transforming an azaarene into the spine of fusedbicyclics via cycloaddition-induced scaffold hopping of 5-Hydroxypyrazoles.Nature communications · 2024Article
- Development and characterization of amino donor-acceptor Stenhouse adducts.Nature communications · 2024Article
- Supramolecular assemblies of amphiphilic donor-acceptor Stenhouse adducts as macroscopic soft scaffolds.Beilstein journal of organic chemistry · 2024Article
- Visible light-responsive materials: the (photo)chemistry and applications of donor-acceptor Stenhouse adducts in polymer science.Chemical Society reviews · 2023Review
- Tethered together: DASA design towards aqueous compatibility.Chemical science · 2023Article
- Visible light activated energy storage in solid-state Azo-BFChemical science · 2023Article
- A Red-Light-Responsive DASA-Polymer with High Water Stability for Controlled Release.Polymers · 2023Article
- Donor-acceptor Stenhouse adduct functionalised polymer microspheres.Polymer chemistry · 2023Article
- Light-Responsive Solid-Solid Phase Change Materials for Photon and Thermal Energy Storage.ACS materials Au · 2023Article
- Harnessing molecular isomerization in polymer gels for sequential logic encryption and anticounterfeiting.Science advances · 2022Article
- Tandem Thio-Michael Addition/Remote Lactone Activation of 5-Hydroxymethylfurfural-Derived δ-Lactone-Fused Cyclopentenones.ChemSusChem · 2022Article
- A Novel Catalytic Route to Polymerizable Bicyclic Cyclic Carbonate Monomers from Carbon Dioxide.Angewandte Chemie (International ed. in English) · 2022Article
- Promoting the Furan Ring-Opening Reaction to Access New Donor-Acceptor Stenhouse Adducts with Hexafluoroisopropanol.Angewandte Chemie (International ed. in English) · 2021Article
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Authors and funding
7 authors.
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Abstract
Donor-acceptor Stenhouse adducts (DASAs) are visible-light-responsive photoswitches with a variety of emerging applications in photoresponsive materials. Their two-step modular synthesis, centered on the nucleophilic ring opening of an activated furan, makes DASAs readily accessible. However, the use of less reactive donors or acceptors renders the process slow and low yielding, which has limited their development. We demonstrate here that 1,1,1,3,3,3-hexafluoro-2-propanol (HFIP) promotes the ring-opening reaction and stabilizes the open isomer, allowing greatly reduced reaction times and increased yields for known derivatives. In addition, it provides access to previously unattainable DASA-based photoswitches and DASA-polymer conjugates. The role of HFIP and the photochromic properties of a set of new DASAs is probed using a combination of
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