Abstract
Fluorinated alkenes exhibit very poor reactivity in copolymerization with non-fluorinated polar monomers such as acrylates. Herein we describe a convenient method for the synthesis of poly(vinyl fluoride-co-acrylic acid) and poly(2-fluoropropene-co-methacrylic acid) copolymers. Thus, the silver-catalyzed decarboxylative radical fluorination of poly(acrylic acid) with Selectfluor in water at room temperature affords poly(vinyl fluoride-co-acrylic acid) copolymers in high yields with well-defined molecular weights and polydispersities. A linear correlation is observed between the extent of fluorination and the amount of Selectfluor, indicating that the copolymer of virtually any monomer ratio can be readily accessed by controlling the amount of Selectfluor. This controlled decarboxylative fluorination is extended to poly(methacrylic acid), leading to well-defined poly(2-fluoropropene-co-methacrylic acid) copolymers.
Highlights
Fluorinated alkenes exhibit very poor reactivity in copolymerization with non-fluorinated polar monomers such as acrylates
The molecular weights and polydispersities of these fluorocopolymers can be well defined, and their monomer ratios can be adjusted at ease
With the increase of the extent of fluorination, the polydispersity index (PDI) gradually increased from 1.38 in 1 to 1.61 in 2i (Selectfluor = 90 mol %). These results indicate that the molecular weights and polydispersities of copolymers 2 are mainly determined by the starting material poly(acrylic acid) 1, while fluorination lowers the molecular weight and slightly increases the PDI in a predictable pattern
Summary
Fluorinated alkenes exhibit very poor reactivity in copolymerization with non-fluorinated polar monomers such as acrylates. The silver-catalyzed decarboxylative radical fluorination of poly(acrylic acid) with Selectfluor in water at room temperature affords poly(vinyl fluoride-co-acrylic acid) copolymers in high yields with well-defined molecular weights and polydispersities. A convenient entry to poly(vinyl fluoride-co-acrylate) and poly(2-fluoropropene-co-methacrylate) copolymers by controlled decarboxylative radical fluorination[26, 27] of poly(meth) acrylic acids is described. With this method, the molecular weights and polydispersities of these fluorocopolymers can be well defined, and their monomer ratios can be adjusted at ease
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