Biobased Cycloolefin Polymers: Carvone-Derived Cyclic Conjugated Diene with Reactive exo-Methylene Group for Regioselective and Stereospecific Living Cationic Polymerization,ACS Macro Letters

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Biobased Cycloolefin Polymers: Carvone-Derived Cyclic Conjugated Diene with Reactive exo-Methylene Group for Regioselective and Stereospecific Living Cationic Polymerization
ACS Macro Letters ( IF 5.1 ) Pub Date : 2020-07-31 , DOI: 10.1021/acsmacrolett.0c00479
Takenori Nishida ₁ , Kotaro Satoh _{1,

2} , Shusaku Nagano ₃ , Takahiro Seki ₁ , Masazumi Tamura ₄ , Yingai Li ₅ , Keiichi Tomishige ₅ , Masami Kamigaito ₁

Affiliation

Carvone, a naturally abundant chiral cyclic α,β-unsaturated carbonyl compound, was chemically transformed into cyclic exo-methylene conjugated dienes. The exo-methylene group had high reactivity in cationic polymerization and was efficiently polymerized in a controlled manner via regioselective 1,4-conjugated additions using initiating systems effective for living cationic polymerization of vinyl ethers. The obtained polymers with 1,3-cyclohexenyl units and tetra-substituted olefins in the main chain showed high glass transition temperatures over 110 °C. The chiral monomer underwent stereospecific polymerization to result in polymers with low solubility and weak packing of the rigid main chain in the lamellar layers. The racemic mixture resulted in soluble amorphous polymers, which were subsequently hydrogenated into cycloolefin polymers with enhanced thermal properties.

中文翻译：

生物基环烯烃聚合物：具有反应性外亚甲基的香芹酮衍生环状共轭二烯用于区域选择性和立体定向活性阳离子聚合

Carvone是一种天然丰富的手性环状α,β-不饱和羰基化合物，被化学转化为环状外-亚甲基共轭二烯。外放_-亚甲基在阳离子聚合中具有高反应性，并且使用对乙烯基醚的活性阳离子聚合有效的引发系统，通过区域选择性 1,4-共轭加成以受控方式有效聚合。所得聚合物在主链中具有 1,3-环己烯基单元和四取代烯烃，其玻璃化转变温度超过 110 °C。手性单体经历立体定向聚合，导致聚合物具有低溶解度和层状层中刚性主链的弱堆积。外消旋混合物产生可溶的无定形聚合物，随后氢化成具有增强热性能的环烯烃聚合物。

更新日期：2020-08-18

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