ArticleJournal of the American Chemical Society2017
Mechanistic Insight into the Photocontrolled Cationic Polymerization of Vinyl Ethers.
Article in Journal of the American Chemical Society, 2017. The graph could read no effect estimate from its abstract, so it casts no vote on the map. Cited by 21 papers.
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Who cites it
21 citing papers in PubMed, 140 citations in OpenAlex.
- Accessing block copolymers with independently modulated tacticities using sequential cationic-anionic polymerization of vinyl ethers and thiiranes.Polymer chemistry · 2026Article
- Combining photocontrolled-cationic and anionic-group-transfer polymerizations using a universal mediator: enabling access to two- and three-mechanism block copolymers.Chemical science · 2024Article
- Using Redox-Switchable Polymerization Catalysis to Synthesize a Chemically Recyclable Thermoplastic Elastomer.Angewandte Chemie (International ed. in English) · 2024Article
- Spotting Trends in Organocatalyzed and Other Organomediated (De)polymerizations and Polymer Functionalizations.Angewandte Chemie (International ed. in English) · 2022Review
- Visible light-controlled living cationic polymerization of methoxystyrene.Nature communications · 2022Article
- Rational Design of Photocatalysts for Controlled Polymerization: Effect of Structures on Photocatalytic Activities.Chemical reviews · 2022Review
- Photons or Electrons? A Critical Comparison of Electrochemistry and Photoredox Catalysis for Organic Synthesis.Chemical reviews · 2022Review
- Light-Mediated Polymerization Induced by Semiconducting Nanomaterials: State-of-the-Art and Future Perspectives.ACS polymers Au · 2021Review
- Sequence Control from Mixtures: Switchable Polymerization Catalysis and Future Materials Applications.Journal of the American Chemical Society · 2021Article
- Continuous-Flow Synthesis of Pyrylium Tetrafluoroborates: Application to Synthesis of Katritzky Salts and Photoinduced Cationic RAFT Polymerization.Organic letters · 2021Article
- Novel perfluoropolyalkylethers monomers: synthesis and photo-induced cationic polymerization.Colloid and polymer science · 2021Article
- Over one century after discovery: pyrylium salt chemistry emerging as a powerful approach for the construction of complex macrocycles and metallo-supramolecules.Chemical science · 2020Review
- Progress and Perspectives Beyond Traditional RAFT Polymerization.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2020Review
- Polymer Nanofibers Exhibiting Remarkable Activity in Driving the Living Polymerization under Visible Light and Reusability.Advanced science (Weinheim, Baden-Wurttemberg, Germany) · 2020Article
- Controlling Polymer Composition in Organocatalyzed Photoredox Radical Ring-Opening Polymerization of Vinylcyclopropanes.Journal of the American Chemical Society · 2019Article
- Controlled Cationic Polymerization: Single-Component Initiation under Ambient Conditions.Journal of the American Chemical Society · 2019Article
- Efficient conversion of ethanol to 1-butanol and CRSC advances · 2019Article
- PET-RAFT Polymerization Catalyzed by Small Organic Molecule under Green Light Irradiation.Polymers · 2019Article
- What happens in the dark? Assessing the temporal control of photo-mediated controlled radical polymerizations.Journal of polymer science. Part A, Polymer chemistry · 2019Article
- On Demand Switching of Polymerization Mechanism and Monomer Selectivity with Orthogonal Stimuli.ACS central science · 2018Article
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Authors and funding
10 authors at 1 institution in 1 country.
Funding
Abstract
The mechanism of the recently reported photocontrolled cationic polymerization of vinyl ethers was investigated using a variety of catalysts and chain-transfer agents (CTAs) as well as diverse spectroscopic and electrochemical analytical techniques. Our study revealed a complex activation step characterized by one-electron oxidation of the CTA. This oxidation is followed by mesolytic cleavage of the resulting radical cation species, which leads to the generation of a reactive cation-this species initiates the polymerization of the vinyl ether monomer-and a dithiocarbamate radical that is likely in equilibrium with the corresponding thiuram disulfide dimer. Reversible addition-fragmentation type degenerative chain transfer contributes to the narrow dispersities and control over chain growth observed under these conditions. Finally, the deactivation step is contingent upon the oxidation of the reduced photocatalyst by the dithiocarbamate radical concomitant with the production of a dithiocarbamate anion that caps the polymer chain end. The fine-tuning of the electronic properties and redox potentials of the photocatalyst in both the excited and the ground states is necessary to obtain a photocontrolled system rather than simply a photoinitiated system. The elucidation of the elementary steps of this process will aid the design of new catalytic systems and their real-world applications.
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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.