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Thiolactone-Functional Reversible Deactivation Radical Polymerization Agents for Advanced Macromolecular Engineering
Macromolecules ( IF 5.1 ) Pub Date : 2018-05-30 00:00:00 , DOI: 10.1021/acs.macromol.8b00770 Marvin Langlais 1 , Olivier Coutelier 1 , Mathias Destarac 1
Macromolecules ( IF 5.1 ) Pub Date : 2018-05-30 00:00:00 , DOI: 10.1021/acs.macromol.8b00770 Marvin Langlais 1 , Olivier Coutelier 1 , Mathias Destarac 1
Affiliation
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The development of innovative, easy to implement strategies for polymer synthesis and modification contributes to pushing back the limits of macromolecular engineering. In this context, thiolactones were highlighted as a new powerful “click” strategy involving an amine–thiol–ene conjugation. In order to further explore the potential of thiolactone chemistry for the field of reversible-deactivation radical polymerization (RDRP), we have developed a toolbox of γ-thiolactone-based RDRP agents including xanthates, bromides, and an alkoxyamine. These RDRP agents were used for the polymerization of more activated and less activated monomers using appropriate RDRP techniques such as RAFT/MADIX, ATRP, and NMP. Well-defined thiolactone-terminated polymers were obtained and characterized for different degrees of polymerizations. An example of thiolactone–telechelic PNIPAM using a thiolactone-based xanthate and an ω-end-chain cyclization strategy was reported. The great reactivity of the thiolactone end-group for postpolymerization modification was proven using primary amines such as benzylamine or propargylamine, which ring-opened the thiolactone with subsequent thiol–thiolsulfonate reaction to scavenge the generated thiol. The original S-naphthalene ethanethiosulfonate was used to give fluorescence properties to the polymers.
中文翻译：
用于高级高分子工程的硫内酯功能可逆失活自由基聚合剂
创新，易于实施的聚合物合成和改性策略的发展有助于降低高分子工程的局限性。在这种情况下，巯基内酯作为一种涉及胺-硫醇-烯键合的新型强大“点击”策略而得到了强调。为了进一步探索硫代内酯化学在可逆失活自由基聚合（RDRP）领域中的潜力，我们开发了一种基于γ-硫代内酯的RDRP试剂的工具箱，其中包括黄药，溴化物和烷氧基胺。这些RDRP试剂用于通过适当的RDRP技术（例如RAFT / MADIX，ATRP和NMP）聚合更多活化和较少活化的单体。获得了明确定义的硫代内酯封端的聚合物，并针对不同的聚合度进行了表征。报告了一个使用基于硫代内酯的黄药和ω-端链环化策略的硫代内酯-telechelic PNIPAM的例子。使用伯胺（如苄胺或炔丙基胺）证明了硫内酯端基对聚合后修饰的反应性很高，这会使硫代内酯开环，随后进行硫醇-硫代磺酸盐反应，以清除生成的硫醇。原本的S-萘乙硫基磺酸盐用于赋予聚合物荧光性质。
更新日期：2018-05-30
中文翻译：
用于高级高分子工程的硫内酯功能可逆失活自由基聚合剂
创新，易于实施的聚合物合成和改性策略的发展有助于降低高分子工程的局限性。在这种情况下，巯基内酯作为一种涉及胺-硫醇-烯键合的新型强大“点击”策略而得到了强调。为了进一步探索硫代内酯化学在可逆失活自由基聚合（RDRP）领域中的潜力，我们开发了一种基于γ-硫代内酯的RDRP试剂的工具箱，其中包括黄药，溴化物和烷氧基胺。这些RDRP试剂用于通过适当的RDRP技术（例如RAFT / MADIX，ATRP和NMP）聚合更多活化和较少活化的单体。获得了明确定义的硫代内酯封端的聚合物，并针对不同的聚合度进行了表征。报告了一个使用基于硫代内酯的黄药和ω-端链环化策略的硫代内酯-telechelic PNIPAM的例子。使用伯胺（如苄胺或炔丙基胺）证明了硫内酯端基对聚合后修饰的反应性很高，这会使硫代内酯开环，随后进行硫醇-硫代磺酸盐反应，以清除生成的硫醇。原本的S-萘乙硫基磺酸盐用于赋予聚合物荧光性质。
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