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首页> 外文期刊>ACS Macro Letters >Preparation of an Aurylated Alkylthiophene Monomer via C-H Activation for Use in Pd-PEPPSI-iPr Catalyzed-Controlled Chain Growth Polymerization
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Preparation of an Aurylated Alkylthiophene Monomer via C-H Activation for Use in Pd-PEPPSI-iPr Catalyzed-Controlled Chain Growth Polymerization

机译：通过C-H活化制备Audlated烷基噻吩单体，用于Pd-PEPPSI-iPr催化控制链增长聚合

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摘要

In the search for new synthetic routes toward greener and more facile syntheses of conjugated polymers, C-H functionalization provides a promising solution by minimizing the production and processing of aryl halide monomer precursors used in traditional organometallic coupling reactions. In this paper, we investigate the use of Au(1) and its ability to directly C-H activate 2-bromo-3-hexylthiophene to form a reactive monomer species, bypassing the typical Grignard monomer formation from a dihalogenated thiophene. Addition of PdPEPPSI-iPr as a palladium catalyst source in the presence of the resultant aurylated thiophene monomer yielded poly(3-hexylthiophene) as observed by both NMR and GPC. Studies on the growth of these polymers show linear dependence between M and monomer conversion, low dispersities, as well as M-n predicted by catalyst loading, which is supportive of a living-type chain growth mechanism. This Au-Pd system represents a novel methodology for incorporating C-H activation into the synthesis of P3HT with control over M-n.
机译：在寻找新的合成路线以更绿色和更方便地合成共轭聚合物时，C-H官能化通过最小化传统有机金属偶联反应中使用的芳基卤化物单体前体的生产和加工提供了一种有前途的解决方案。在本文中，我们研究了Au（1）的使用及其直接C-H活化2-溴-3-己基噻吩形成反应性单体的能力，绕过了由二卤代噻吩形成的典型格利雅单体的形成。如通过NMR和GPC所观察到的，在所得的酰化噻吩单体的存在下，添加PdPEPPSI-iPr作为钯催化剂源，产生了聚（3-己基噻吩）。对这些聚合物生长的研究表明，M与单体转化率，低分散性以及催化剂负载预测的M-n之间呈线性关系，这支持了活性型链增长机制。该Au-Pd系统代表了一种新颖的方法，可将C-H激活结合到对M-n进行控制的P3HT合成中。

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