Synthesis and Closed-Loop Recycling of Self-Immolative Poly(dithiothreitol),Macromolecules

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Synthesis and Closed-Loop Recycling of Self-Immolative Poly(dithiothreitol)
Macromolecules ( IF 5.1 ) Pub Date : 2020-06-09 , DOI: 10.1021/acs.macromol.0c00861
Sunirmal Pal ₁ , Andreas Sommerfeldt ₁ , Maiken B. Davidsen ₁ , Mogens Hinge ₂ , Steen U. Pedersen ₁ , Kim Daasbjerg ₁

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Self-immolative polymers (SIPs) are promising members of the emerging class of recyclable polymers with the ability to end-to-end depolymerize to their monomers. Unfortunately, SIPs are often synthesized by cumbersome procedures at low temperatures in protected atmosphere. In this study, a SIP with a novel poly(disulfide) backbone is introduced, using dl-dithiothreitol (DTT) as the monomer. Remarkably, poly(DTT) can be produced by solid-state polymerization in a robust and easily scalable process by mechanically mixing DTT with 2,2′-dithiodipyridine as the end-capping agent. The new polymer possesses good thermal and chemical stabilities, but once its depolymerization is triggered, this proceeds smoothly within minutes to afford cyclic DTT because of a favorable intramolecular back-biting thiol–disulfide exchange reaction in the polymer backbone. As a proof of concept, the cyclic DTT waste was recovered, reduced to DTT monomer, and repolymerized in a closed-loop approach.

中文翻译：

自焚聚二硫苏糖醇的合成及闭环循环

自焚聚合物（SIP）是新兴的可回收聚合物中有希望的成员，具有端到端解聚为单体的能力。不幸的是，SIP经常在保护气氛下在低温下通过繁琐的步骤合成。在这项研究中，使用dl引入了具有新型聚二硫键主链的SIP-二硫苏糖醇（DTT）作为单体。值得注意的是，聚（DTT）可以通过将DTT与作为封端剂的2,2'-二硫代二吡啶机械混合而在一种坚固且易于扩展的过程中通过固态聚合生产。这种新的聚合物具有良好的热稳定性和化学稳定性，但是一旦引发解聚反应，由于聚合物主链中分子间有利的咬位巯基-二硫键交换反应，该反应可在数分钟内顺利进行，以生成环状DTT。作为概念证明，将环状DTT废料回收，还原为DTT单体，然后以闭环方式进行聚合。

更新日期：2020-06-23

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