Buckybowl polymers: synthesis of corannulene-containing polymers through post-polymerization modification strategy,Polymer Chemistry

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Buckybowl polymers: synthesis of corannulene-containing polymers through post-polymerization modification strategy
Polymer Chemistry ( IF 4.1 ) Pub Date : 2021-08-24 , DOI: 10.1039/d1py00664a
Viktor Barát ₁ , Taejun Eom ₂ , Anzar Khan ₂ , Mihaiela C. Stuparu ₁

Affiliation

In this study, we explore the synthesis of methacrylate polymers carrying buckybowl corannulene as the polymer side-chain. For this, a general reactive scaffold, poly(glycidyl methacrylate) (PGMA), was prepared through an atom transfer radical polymerization process. The glycidyl units of this polymer could be subjected to a nucleophilic ring-opening reaction with mercaptocorannulene. The ring-opening reaction produced a reactive secondary hydroxyl group. These sites could be used to anchor alkyl chains through an esterification reaction. Alternatively, the post-polymerization functionalization could be carried out in one step albeit in a random fashion using two different thiol molecules. Here, the incorporation of an electron-rich thienothiophene moiety is demonstrated along with electron-deficient corannulenes in the polymer chain. The PGMA homopolymer could also be replaced with a random copolymer of methyl methacrylate. In some cases, the ring-opening reaction is carried out only partially to retain the reactive epoxide groups in the molecular structure, which enables further functionalization to alter polymer solubility or allow for intermolecular crosslinking of the structure to obtain thick polymer films. In essence, various simple synthetic strategies to corannulene-encoded and reactive/functionalizable polymers are established in this work.

中文翻译：

Buckybowl 聚合物：通过聚合后改性策略合成含芴烯的聚合物

在这项研究中，我们探索了以巴克碗环烯作为聚合物侧链的甲基丙烯酸酯聚合物的合成。为此，通过原子转移自由基聚合过程制备了通用的反应性支架聚（甲基丙烯酸缩水甘油酯）（PGMA）。该聚合物的缩水甘油基单元可以与巯基二环烯进行亲核开环反应。开环反应产生反应性仲羟基。这些位点可用于通过酯化反应锚定烷基链。或者，聚合后官能化可以在一个步骤中进行，尽管以随机方式使用两种不同的硫醇分子。在这里，富含电子的噻吩并噻吩部分与聚合物链中缺电子的芴烯一起被证明。PGMA均聚物也可以用甲基丙烯酸甲酯的无规共聚物代替。在某些情况下，仅部分地进行开环反应以保留分子结构中的反应性环氧基团，这使得进一步官能化以改变聚合物溶解度或允许结构的分子间交联以获得厚聚合物膜。从本质上讲，在这项工作中建立了各种简单的合成策略来合成 coranulene 编码和反应性/功能化聚合物。这使得进一步官能化以改变聚合物溶解度或允许结构的分子间交联以获得厚聚合物膜。从本质上讲，在这项工作中建立了各种简单的合成策略来合成 coranulene 编码和反应性/功能化聚合物。这使得进一步官能化以改变聚合物溶解度或允许结构的分子间交联以获得厚聚合物膜。从本质上讲，在这项工作中建立了各种简单的合成策略来合成 coranulene 编码和反应性/功能化聚合物。

更新日期：2021-08-31

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