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Elucidating Monomer Character of an Alkenyl Boronate through Radical Copolymerization Leads to Copolymer Synthesis beyond the Limitation of Copolymerizability by Side-Chain Replacement
ACS Macro Letters ( IF 5.8 ) Pub Date : 2020-05-18 , DOI: 10.1021/acsmacrolett.0c00287
Hiroshi Makino 1 , Tsuyoshi Nishikawa 1 , Makoto Ouchi 1
Affiliation  

Isopropenyl boronic acid pinacol ester (IPBpin) was used as a comonomer in radical polymerization with a wide range of common vinyl monomers for elucidation of the monomer character and syntheses of conventionally inaccessible copolymers via the replacement of the boron pendant. The study revealed that the boron-containing monomer is categorized into an electron-rich conjugated monomer, which was well consistent with the results of density functional theory (DFT)-based investigation. One of the thus obtained copolymers, the IPBpin–styrene copolymer, was successfully transformed into an α-methyl vinyl alcohol (MVA)–styrene counterpart via oxidation of the boron pendant. The copolymer cannot be synthesized even with the acetyl-protected monomer instead of IPBpin due to poor copolymerization ability based on the nonconjugated character.

中文翻译:

通过自由基共聚阐明硼酸烯基酯的单体特性使共聚物合成超越了侧链置换的共聚性限制

异丙烯基硼酸频哪醇酯 (IPBpin) 被用作自由基聚合中的共聚单体,用于与各种常见的乙烯基单体进行自由基聚合,以阐明单体特性并通过更换硼侧基来合成传统上难以接近的共聚物。该研究表明,含硼单体被归类为富电子共轭单体,这与基于密度泛函理论(DFT)的研究结果非常一致。由此获得的共聚物之一,IPBpin-苯乙烯共聚物,通过硼侧基的氧化成功地转化为α-甲基乙烯醇(MVA)-苯乙烯对应物。由于基于非共轭特性的共聚能力差,即使使用乙酰基保护的单体代替 IPBpin 也不能合成共聚物。
更新日期:2020-05-18
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