Brønsted Acid Catalyzed Stereoselective Polymerization of Vinyl Ethers
| Autor: | Travis P. Varner, Frank A. Leibfarth, Paige E Jacky, Aaron J. Teator, Phil C. Knutson, Caleb T Kozuszek |
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| Rok vydání: | 2021 |
| Předmět: |
organic chemicals
technology industry and agriculture Oxocarbenium Chain transfer macromolecular substances General Chemistry Vinyl ether Biochemistry Catalysis chemistry.chemical_compound Colloid and Surface Chemistry Monomer Polymerization chemistry Polymer chemistry medicine Lewis acids and bases Brønsted–Lowry acid–base theory medicine.drug |
| Zdroj: | Journal of the American Chemical Society. 143:16388-16393 |
| ISSN: | 1520-5126 0002-7863 |
| DOI: | 10.1021/jacs.1c08282 |
| Popis: | Isotactic poly(vinyl ether)s (PVEs) have recently been identified as a new class of semicrystalline thermoplastics with a valuable combination of mechanical and interfacial properties. Currently, methods to synthesize isotactic PVEs are limited to strong Lewis acids that require a high catalyst loading and limit the accessible scope of monomer substrates for polymerization. Here, we demonstrate the first Bronsted acid catalyzed stereoselective polymerization of vinyl ethers. A single-component imidodiphosphorimidate catalyst exhibits a sufficiently low pKa to initiate vinyl ether polymerization and acts as a chiral conjugate base to direct the stereochemistry of monomer addition to the oxocarbenium ion reactive chain end. This Bronsted acid catalyzed stereoselective polymerization enabled an expanded substrate scope compared to previous methods, the use of chain transfer agents to lower catalyst loading, and the capability to recycle the catalyst for multiple polymerizations. |
| Databáze: | OpenAIRE |
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