Soluble Polymer Precursors via Ring-Expansion Metathesis Polymerization for the Synthesis of Cyclic Polyacetylene,Macromolecules

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Soluble Polymer Precursors via Ring-Expansion Metathesis Polymerization for the Synthesis of Cyclic Polyacetylene
Macromolecules ( IF 5.1 ) Pub Date : 2021-09-01 , DOI: 10.1021/acs.macromol.1c00938
Zhihui Miao _{1,

2} , Debabrata Konar ₂ , Brent S. Sumerlin ₂ , Adam S. Veige _{1,

2}

Affiliation

Cyclic polyacetylene (c-PA) is the cyclic derivative of the semiconducting linear polyacetylene. As with the linear derivative, cyclic polyacetylene is insoluble, making its characterization and processing challenging. Herein, we report the synthesis of c-PA via an indirect approach, employing ring-expansion metathesis polymerization of cyclic alkenes to form soluble polymer precursors. Subsequent retro-Diels–Alder elimination through heating provides c-PA. Dilute solution characterizations of the polymer precursors including ¹H nuclear magnetic resonance spectroscopy, gel permeation chromatography, and infrared and Raman spectroscopy confirm their cyclic structure and, by inference, the cyclic topology of the resulting c-PA. Solid-state thermal analyses via thermogravimetric analysis and differential scanning calorimetry reveal the chemical and physical transformations occurring during the retro-Diels–Alder elimination step and concurrent isomerization. Freestanding films are attainable via the soluble precursors, and when doped with I₂, the films are semiconducting.

中文翻译：

通过环膨胀复分解聚合合成环状聚乙炔的可溶性聚合物前体

环状聚乙炔 ( c -PA ) 是半导体线性聚乙炔的环状衍生物。与线性衍生物一样，环状聚乙炔是不溶性的，这使得其表征和加工具有挑战性。在此，我们报告了通过间接方法合成c- PA，采用环烯烃的扩环复分解聚合形成可溶性聚合物前体。随后通过加热进行的逆狄尔斯-阿尔德消除提供c- PA。聚合物前体的稀溶液表征，包括¹H 核磁共振光谱、凝胶渗透色谱以及红外和拉曼光谱证实了它们的环状结构，并由此推断出所得c- PA的环状拓扑结构。通过热重分析和差示扫描量热法进行的固态热分析揭示了在逆狄尔斯-阿尔德消除步骤和并发异构化过程中发生的化学和物理转变。独立薄膜可通过可溶性前体获得，并且当掺杂有 I _{2 时}，薄膜是半导体的。

更新日期：2021-09-14

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