Highly Efficient and para-Selective C–H Functionalization of Polystyrene Providing a Versatile Platform for Diverse Applications,ACS Macro Letters

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Highly Efficient and para-Selective C–H Functionalization of Polystyrene Providing a Versatile Platform for Diverse Applications
ACS Macro Letters ( IF 5.1 ) Pub Date : 2022-10-19 , DOI: 10.1021/acsmacrolett.2c00541
Boxin Xue ₁ , Pan-Pan Huang ₁ , Ming-Zhi Zhu ₁ , Shu-Qing Fu ₁ , Ji-Hong Ge ₁ , Xingguang Li ₁ , Pei-Nian Liu ₁

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Postpolymerization modification of polystyrene (PS) can afford numerous value-added materials with different functions and applications, but it has been hampered by the lack of efficient methods. We report herein a highly efficient and para-selective conversion of the C–H bonds of the aromatic ring of PS into diverse functional groups using a combination of thianthrenation and thio-Suzuki–Miyaura coupling reaction. Notably, the thianthrenation efficiency of PS is as high as 99% and the degree of thianthrenation can be conveniently controlled using stoichiometric tuning of the amount of thianthrene-S-oxide added, resulting in 24–99 mol % thianthrenation. In the subsequent thio-Suzuki–Miyaura coupling reaction, 18 functionalized PS containing various functional groups (-CH₂OH, -OMe, -SMe, -OTBS, -CH₃, -NHBoc, -OCOMe, -CHO, -COMe, -Si(Me)₃, etc.) were successfully prepared with a high degree of functionalization (64–99 mol %). The obtained functionalized PS can be readily converted into diverse functional materials, including solid-phase synthesis resins, aggregation-induced emission fluorophores, as well as ionomer binders and ion-exchange membranes for energy conversion devices. This method imparts diverse functionality onto PS with extremely high efficiency and selectivity, providing a versatile platform to transform existing commodity PS plastics into high-performance materials.

中文翻译：

聚苯乙烯的高效对位选择性 C-H 官能化为多种应用提供了多功能平台

聚苯乙烯（PS）的后聚合改性可以提供许多具有不同功能和应用的增值材料，但由于缺乏有效的方法而受到阻碍。我们在此报告了使用噻蒽化和硫-铃木-宫浦偶联反应的组合，将 PS 芳环的 C-H 键高效和对位选择性地转化为不同的官能团。值得注意的是，PS 的噻蒽化效率高达 99%，并且可以通过化学计量调整添加的噻蒽-S-氧化物的量来方便地控制噻蒽化程度，从而实现 24-99 mol% 的噻蒽化。在随后的 thio-Suzuki–Miyaura 偶联反应中，18 个功能化的 PS 含有不同的官能团（-CH ₂OH、-OMe、-SMe、-OTBS、-CH ₃、-NHBoc、-OCOMe、-CHO、-COMe、-Si(Me) ₃等）成功制备并具有高度功能化（64–99摩尔％）。获得的功能化 PS 可以很容易地转化为多种功能材料，包括固相合成树脂、聚集诱导发光荧光团，以及用于能量转换装置的离聚物粘合剂和离子交换膜。这种方法以极高的效率和选择性赋予 PS 多种功能，为将现有商品 PS 塑料转化为高性能材料提供了一个多功能平台。

更新日期：2022-10-19

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