Reactive Processing of Furan-Based Monomers via Frontal Ring-Opening Metathesis Polymerization for High Performance Materials,Advanced Materials

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Reactive Processing of Furan-Based Monomers via Frontal Ring-Opening Metathesis Polymerization for High Performance Materials
Advanced Materials ( IF 27.4 ) Pub Date : 2024-07-22 , DOI: 10.1002/adma.202405736
Zhenchuang Xu _{1,

2} , Lauren Chua ₃ , Avni Singhal ₃ , Pranav Krishnan _{1,

4} , Jacob J Lessard _{1,

2} , Benjamin A Suslick _{1,

2} , Valerie Chen _{1,

2} , Nancy R Sottos _{1,

4} , Rafael Gomez-Bombarelli ₃ , Jeffrey S Moore _{1,

2}

Affiliation

Frontal ring-opening metathesis polymerization (FROMP) presents an energy-efficient approach to produce high-performance polymers, typically utilizing norbornene derivatives from Diels–Alder reactions. This study broadens the monomer repertoire for FROMP, incorporating the cycloaddition product of biosourced furan compounds and benzyne, namely 1,4-dihydro-1,4-epoxynaphthalene (HEN) derivatives. A computational screening of Diels–Alder products is conducted, selecting products with resistance to retro-Diels–Alder but also sufficient ring strain to facilitate FROMP. The experiments reveal that varying substituents both modulate the FROMP kinetics and enable the creation of thermoplastic materials characterized by different thermomechanical properties. Moreover, HEN-based crosslinkers are designed to enhance the resulting thermomechanical properties at high temperatures (>200 °C). The versatility of such materials is demonstrated through direct ink writing (DIW) to rapidly produce 3D structures without the need for printed supports. This research significantly extends the range of monomers suitable for FROMP, furthering efficient production of high-performance polymeric materials.

中文翻译：

通过前开环复分解聚合反应加工呋喃基单体制备高性能材料

正面开环复分解聚合（FROMP）提供了一种生产高性能聚合物的节能方法，通常利用狄尔斯-阿尔德反应中的降冰片烯衍生物。这项研究拓宽了 FROMP 的单体库，纳入了生物源呋喃化合物和苯炔的环加成产物，即 1,4-二氢-1,4-环氧萘 ( HEN ) 衍生物。对 Diels-Alder 产品进行计算筛选，选择具有逆 Diels-Alder 抗性但也有足够环应变以促进 FROMP 的产品。实验表明，不同的取代基既可以调节 FROMP 动力学，又可以产生具有不同热机械性能的热塑性材料。此外，基于HEN的交联剂旨在增强高温 (>200 °C) 下的热机械性能。此类材料的多功能性通过直接墨水书写 (DIW) 得以证明，无需印刷支撑即可快速生成 3D 结构。这项研究显着扩展了适用于 FROMP 的单体范围，进一步提高了高性能聚合物材料的高效生产。

更新日期：2024-07-22

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