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p-Cymene: A Sustainable Solvent that is Highly Compatible with Direct Arylation Polymerization (DArP)

机译:P-Cyhe:一种可持续溶剂,其与直接芳基化聚合高度相容(DARP)

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摘要

For over a decade, Direct Arylation Polymerization (DArP) has been demonstrated to be an eco-friendly, facile, and low-cost alternative to conventional methodologies such as Stille polymerization for conjugated polymer synthesis. By accessing through a C-H activation pathway, DArP offers a reduction of synthetic steps while eliminating the generation of stoichiometric, highly toxic organotin byproducts. However, as the major component in these reactions, the solvents most prevalently employed for DArP are hazardous and produced from unsustainable sources, such as dimethylacetamide (DMA), tetrahydrofuran (THF), and toluene. Although the use of sustainable alternative solvents such as 2-MeTHF and cyclopentyl methyl ether (CPME) has recently emerged, drawbacks of ethereal solvents include the need for a pressurized reaction setup as well as potential peroxide formation. While aromatic solvents are superior in solubilizing conjugated polymers, very little has been done in searching for more sustainable, benign alternatives for this class of solvent. Herein, we report the application of a sustainable, naturally sourced, high-boiling aromatic solvent, p-cymene, to DArP for the first time. p-Cymene was found to display excellent solubilizing ability in the synthesis of a broad scope of alternating copolymers with M-r, up to 51.3 kg/mol and yields up to 96.2%, outperforming those prepared using CPME and toluene. Structural analysis revealed the exclusion of defects in these polymers prepared using p-cymene as the solvent which, in the case of a 2,2'-bithiophene monomer, is challenging to access through the use of conventional solvents for DArP, such as DMA and toluene.
机译:None

著录项

  • 来源
    《ACS Macro Letters》 |2021年第6期|共6页
  • 作者

    Ye Liwei; Thompson Barry C.;

  • 作者单位

    Univ Southern Calif Dept Chem Los Angeles CA 90089 USA;

    Univ Southern Calif Dept Chem Los Angeles CA 90089 USA;

  • 收录信息
  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 有机化学;
  • 关键词

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