Combining Click Sulfur(VI)‐Fluoride Exchange with Photoiniferters: A Facile, Fast, and Efficient Strategy for Postpolymerization Modification,Macromolecular Rapid Communications

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Combining Click Sulfur(VI)‐Fluoride Exchange with Photoiniferters: A Facile, Fast, and Efficient Strategy for Postpolymerization Modification
Macromolecular Rapid Communications ( IF 4.2 ) Pub Date : 2017-11-16 , DOI: 10.1002/marc.201700523
Peixi Wang ₁ , Yishi Dong ₁ , Xiaowen Lu ₁ , Zhaoqiang Wu ₁ , Hong Chen ₁

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“Click” type reactions represent the currently most prevalent postpolymerization strategy for the preparation of functional polymeric materials. Herein, a novel photoiniferter agent 4‐(fluorosulfonyl)benzyl diethylcarbamodithioate (FSB‐DECT) containing both dithiocarbamates and sulfonyl fluoride moieties is developed to act as both photoinitiator and click sulfur(VI)‐fluoride exchange (SuFEx) agent. The photopolymerization behavior of FSB‐DECT is demonstrated via standard photoiniferter‐mediated polymerization for various types of monomer including N‐isopropylacrylamide (NIPAAm), glycidyl methacrylate, and vinyl acetate (VAc). Gel permeation chromatography data show that the polymerization is relatively well controlled, with polydispersity indices of the product homopolymers in the range of 1.3–1.6. ¹H and ¹⁹F NMR spectra and “reinitiated” photopolymerization indicate that the sulfonyl fluoride and diethyldithiocarbamyl groups remain at the respective ends of the homopolymer chains. Furthermore, using the sulfonyl fluoride end‐functionalized poly(N‐isopropylacrylamide) as a model polymer, the utility of the SuFEx reaction for efficient postpolymerization functionalization is demonstrated.

中文翻译：

结合点击硫（VI）-氟化物交换与光引发剂：一种简便，快速，高效的后聚合修饰策略。

“点击”型反应代表了目前制备功能性聚合材料最普遍的后聚合策略。本文中，开发了一种同时含有二硫代氨基甲酸酯和磺酰氟的新型光引发剂4-（氟磺酰基）苄基二乙基氨基甲二硫酸酯（FSB-DECT），既可以用作光引发剂，又可以用作单击硫（VI）-氟交换剂（SuFEx）。FSB-DECT的光聚合行为已通过标准光引发剂介导的各种单体（包括N-异丙基丙烯酰胺（NIPAAm），甲基丙烯酸缩水甘油酯和乙酸乙烯酯（VAc））进行了证明。凝胶渗透色谱数据表明，聚合反应相对较好，产物均聚物的多分散指数在1.3-1.6范围内。¹ H和¹⁹ F NMR光谱和“重新引发”的光聚合表明，磺酰氟和二乙基二硫代氨基甲酰基保留在均聚物链的各个末端。此外，使用磺酰氟末端官能化的聚（N-异丙基丙烯酰胺）作为模型聚合物，证明了SuFEx反应可用于有效的后聚合官能化。

更新日期：2017-11-16

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