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Nucleophilic fluoroalkylation as an efficient avenue to achieve fluorinated polyimide monomers containing Csp3‐Rf from carbonyl compounds
Journal of Polymer Science ( IF 3.9 ) Pub Date : 2020-07-16 , DOI: 10.1002/pol.20200208 Yongjian Li 1 , Zhongkai Wang 1 , Tangsong Zhu 1 , Haixia Qi 1 , Lei Xiong 1 , Feng Liu 1
Journal of Polymer Science ( IF 3.9 ) Pub Date : 2020-07-16 , DOI: 10.1002/pol.20200208 Yongjian Li 1 , Zhongkai Wang 1 , Tangsong Zhu 1 , Haixia Qi 1 , Lei Xiong 1 , Feng Liu 1
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Fluorinated polyimides (PIs) have gained increasing attention due to their high transparency and low dielectric constant. However, the access to fluorinated monomers is limited, with most of the fluorination based on transformation from C─H to C─F. This article presents a new avenue to achieve fluorinated monomers starting from wide range of carbonyl compounds. Nucleophilic fluoroalkylation on carbonyl using Ruppert's reagent has been employed to transform carbonyl (CO) into α‐trifluoromethylated alcohol followed by facile derivation into diamine containing Csp3─CF3. The obtained symmetric fluorinated diamine para‐bis(1′‐[3‐amino‐6‐pyridinyloxy]‐1′‐trifluoromethyl)benzene (PAPyTB) show good modification effects on PIs. The PIs modified by PAPyTB exhibit the generally maintained optical transparency and Tg. The mechanical properties of modified PIs show a wide range and decrease with increasing content of PAPyTB. Importantly, the solubility and hydrophobicity of the modified PIs increase with increasing loading of PAPyTB. Furthermore, the presence of trifluoromethyl groups in the polymer chain leads to reduced dielectric constant of the modified PIs, showing dielectric constant (ε′) 3.16 and dielectric loss (ε″) 0.0052 at 1 MHz and 298 K with 60% molar content of PAPyTB. This work indicates that nucleophilic fluoroalkylation is a new and efficient avenue to achieve fluorinated PI monomers with Csp3─Rf from a wide range of carbonyl compounds.
中文翻译：
亲核性氟烷基化是从羰基化合物获得含Csp3-Rf的氟化聚酰亚胺单体的有效途径
氟化聚酰亚胺（PI）由于其高透明度和低介电常数而受到越来越多的关注。但是，氟化单体的获取受到限制，大部分氟化基于从CH到C的转变。本文提出了一种从多种羰基化合物开始获得氟化单体的新途径。使用Ruppert的试剂上的亲核羰氟烷基已被用于转化羰基（CO）成α-三氟甲基化醇，随后容易导出到含有CSP二胺3 ─CF 3。所获得的对称氟化二胺对双（1'-[3-氨基-6-吡啶氧基] -1'-三氟甲基）苯（PAPyTB）对PI表现出良好的修饰效果。经PAPyTB修饰的PI表现出通常保持的光学透明度和T g。改性PI的机械性能表现出广泛的范围，并且随着PAPyTB含量的增加而降低。重要的是，修饰的PI的溶解度和疏水性随PAPyTB的负载增加而增加。此外，聚合物链中三氟甲基的存在导致改性的PI的介电常数降低，显示介电常数（ε '）3.16和介电损耗（ε''）0.0052在1 MHz和298 K下具有60％的PAPyTB摩尔含量。这项工作表明，亲核氟烷基化是一种新的和有效的途径，以实现与CSP氟化PI单体3 ─R ˚F从广泛的羰基化合物。
更新日期：2020-07-16
中文翻译：
亲核性氟烷基化是从羰基化合物获得含Csp3-Rf的氟化聚酰亚胺单体的有效途径
氟化聚酰亚胺（PI）由于其高透明度和低介电常数而受到越来越多的关注。但是，氟化单体的获取受到限制，大部分氟化基于从CH到C的转变。本文提出了一种从多种羰基化合物开始获得氟化单体的新途径。使用Ruppert的试剂上的亲核羰氟烷基已被用于转化羰基（CO）成α-三氟甲基化醇，随后容易导出到含有CSP二胺3 ─CF 3。所获得的对称氟化二胺对双（1'-[3-氨基-6-吡啶氧基] -1'-三氟甲基）苯（PAPyTB）对PI表现出良好的修饰效果。经PAPyTB修饰的PI表现出通常保持的光学透明度和T g。改性PI的机械性能表现出广泛的范围，并且随着PAPyTB含量的增加而降低。重要的是，修饰的PI的溶解度和疏水性随PAPyTB的负载增加而增加。此外，聚合物链中三氟甲基的存在导致改性的PI的介电常数降低，显示介电常数（ε '）3.16和介电损耗（ε''）0.0052在1 MHz和298 K下具有60％的PAPyTB摩尔含量。这项工作表明，亲核氟烷基化是一种新的和有效的途径，以实现与CSP氟化PI单体3 ─R ˚F从广泛的羰基化合物。
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