Productive Exchange of Thiols and Thioesters to Form Dynamic Polythioester-Based Polymers,ACS Macro Letters

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Productive Exchange of Thiols and Thioesters to Form Dynamic Polythioester-Based Polymers
ACS Macro Letters ( IF 5.1 ) Pub Date : 2018-10-16 00:00:00 , DOI: 10.1021/acsmacrolett.8b00611
Chen Wang ₁ , Sudheendran Mavila ₁ , Brady T Worrell ₁ , Weixian Xi ₁ , Trevor M Goldman ₁ , Christopher N Bowman ₁

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Polymers that possess dynamic covalent bonds activated at ambient conditions are ideal platforms for smart, responsive materials. Herein, a class of dynamic covalent polymerizations is developed based on the thiol-thioester exchange, that is, transthioesterification, reaction. Shifts in the equilibrium extent of the exchange reactions are deliberately utilized to drive the formation of oligomers and polymers. In particular, a series of AB and A₂-B₂ monomers, including amino acid derivatives, were polymerized rapidly by catalytic amounts of mild bases in various organic solvents under ambient conditions. Thioester backbone oligopeptides, including cysteine and glycine, were obtained with an average repeating unit of four and a PDI of 1.8. Further, structurally dynamic hydrogels were obtained by such reactions between four-armed poly(ethylene glycol)-10000 based monomers in neutral water. These hydrogels showed dynamic, frequency-dependent flow behavior between sol and gel states.

中文翻译：

硫醇和硫酯的生产性交换形成动态聚硫酯基聚合物

具有在环境条件下活化的动态共价键的聚合物是智能响应材料的理想平台。在此，基于硫醇-硫酯交换，即转硫酯化反应，开发了一类动态共价聚合。有意利用交换反应平衡程度的变化来驱动低聚物和聚合物的形成。特别是一系列 AB 和 A ₂ -B ₂包括氨基酸衍生物在内的单体在环境条件下通过催化量的温和碱在各种有机溶剂中快速聚合。硫酯骨架寡肽，包括半胱氨酸和甘氨酸，平均重复单元为 4，PDI 为 1.8。此外，通过四臂聚（乙二醇）-10000 基单体在中性水中的这种反应获得了结构动态的水凝胶。这些水凝胶在溶胶和凝胶状态之间表现出动态的、频率相关的流动行为。

更新日期：2018-10-16

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