2-(Benzylthio)ethyl Glycidyl Ether: A Gateway to Redox-Responsive Polyethers,Macromolecules

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2-(Benzylthio)ethyl Glycidyl Ether: A Gateway to Redox-Responsive Polyethers
Macromolecules ( IF 5.1 ) Pub Date : 2024-08-29 , DOI: 10.1021/acs.macromol.4c00949
Ahyun Kim ₁ , Jinsu Baek ₁ , Byeong-Su Kim ₁

Affiliation

This work presents the design and synthesis of a functional epoxide monomer, 2-(benzylthio)ethyl glycidyl ether (BTGE), serving as a versatile building block for the development of redox-responsive polyethers. It details the successful synthesis of a series of poly(2-(benzylthio)ethyl glycidyl ether) (PBTGE) homopolymers and ABA-type triblock copolymers (i.e., PBTGE-b-PEO-b-PBTGE), achieved through controlled anionic ring-opening polymerization of the BTGE using a poly(ethylene oxide) (PEO) macroinitiator. Comprehensive characterization of the synthesized monomers and polymers was performed employing various analytical techniques, such as ¹H- and ¹³C NMR, GPC, FT-IR spectroscopy, and MALDI-ToF mass spectrometry. These polymers demonstrate unique redox-responsive behavior, characterized by an oxidation-induced transition from hydrophobic to hydrophilic states and a reductive deprotection to generate free thiol groups. Furthermore, the PBTGE-b-PEO-b-PBTGE triblock copolymers have been utilized to form physically cross-linked hydrogels through the strong hydrophobic interactions of the end blocks. Notably, these hydrogels undergo a gel-to-sol transition under oxidative conditions, as evidenced by rheological analysis. This study highlights the potential of the BTGE monomer as a versatile building block for the development of advanced materials with dual redox-responsive functionalities.

中文翻译：

2-(苄硫基)乙基缩水甘油醚：氧化还原响应性聚醚的途径

这项工作介绍了功能性环氧化物单体 2-(苄硫基)乙基缩水甘油醚 (BTGE) 的设计和合成，该单体可作为开发氧化还原响应性聚醚的通用构建模块。它详细介绍了一系列聚（2-（苄硫基）乙基缩水甘油醚）（PBTGE）均聚物和ABA型三嵌段共聚物（即PBTGE- b -PEO- b -PBTGE）的成功合成，这是通过控制阴离子环-实现的。使用聚环氧乙烷 (PEO) 大分子引发剂进行 BTGE 的开环聚合。采用各种分析技术对合成的单体和聚合物进行了综合表征，例如¹ H 和¹³ C NMR、GPC、FT-IR 光谱和 MALDI-ToF 质谱。这些聚合物表现出独特的氧化还原响应行为，其特征是氧化诱导的从疏水态到亲水态的转变以及还原脱保护以产生游离硫醇基团。此外，PBTGE- b -PEO- b -PBTGE三嵌段共聚物已被用来通过末端嵌段的强疏水相互作用形成物理交联的水凝胶。值得注意的是，如流变学分析所证明，这些水凝胶在氧化条件下经历凝胶到溶胶的转变。这项研究强调了 BTGE 单体作为多功能构建块的潜力，用于开发具有双重氧化还原响应功能的先进材料。

更新日期：2024-08-29

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