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Click chemistry approaches to expand the repertoire of PEG-based fluorinated surfactants for droplet microfluidics

机译:点击化学方法以扩大液滴微流体的PEG基氟化表面活性剂的曲目

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摘要

We report the novel and simplified synthesis of fluorinated surfactants for droplet microfluidics. The range of applications of droplet microfluidics has greatly expanded during the last decade thanks to its ability to manipulate and process tiny amount of sample and reagents at high throughput in independent reactors. A critical component of the technology is the formulation of the immiscible oil phase that contains surfactants to stabilize droplets. The success of droplet microfluidics relies mostly on a single fluorinated formulation that uses a PFPE-PEG triblock surfactant. The synthesis of this surfactant is laborious and requires skills in synthetic chemistry preventing the wider community to explore the synthesis of surfactants with alternate structures. We sought to provide a simplified synthesis for novel PFPE-PEG surfactants based on click chemistry approaches such as copper-catalyzed azide-alkyne cycloaddition (CuAAC) and UV-activated thiol-yne reactions. Our strategy is based on converting a moisture sensitive intermediate typically used in the synthesis of the triblock PFPE-PEG surfactant into a stable and click ready molecule. We successfully combined that fluorinated tail with differently functionalized PEG and glycerol ethoxylate molecules to generate surfactants with diverse structures via CuACC and thiol-yne reactions. We report the characterization, biocompatibility and ability to stabilize emulsions of those surfactants, as well as the unique advantages and challenges of the strategy.
机译:我们报告了对液滴微流体的氟化表面活性剂的新颖和简化的合成。由于能够在独立反应器中以高通量的高通量进行操纵和处理微量样品和试剂,在过去十年中,液滴微流体的应用范围大大扩展。该技术的关键组分是配制含有表面活性剂以稳定液滴的不混溶油相。液滴微流体的成功主要依赖于使用PFPE-PEG三嵌段表面活性剂的单一氟化制剂。这种表面活性剂的合成是费力的,需要合成化学的技能,防止更广泛的群落探讨具有交替结构的表面活性剂的合成。我们寻求为基于铜催化的吡啶氧化物 - 炔环加油(Cuaac)和UV活化的硫醇-yniol-yne反应提供基于点击化学方法的新型PFPE-PEG表面活性剂的简化合成。我们的策略基于将通常用于合成三嵌段PFPE-PEG表面活性剂的水分敏感的中间体转化为稳定的并点击就绪分子。我们成功地将氟化尾与不同官能化的PEG和甘油乙氧基化物分子组合以产生通过CACC和硫醇-YNE反应产生具有不同结构的表面活性剂。我们报告了稳定这些表面活性剂乳液的表征,生物相容性和能力,以及策略的独特优势和挑战。

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  • 来源
    《RSC Advances》 |2018年第23期|共15页
  • 作者单位

    MIT Dept Chem Cambridge MA 02139 USA;

    SUNY Stony Brook Dept Biomed Engn Stony Brook NY 11794 USA;

    SUNY Stony Brook Dept Biomed Engn Stony Brook NY 11794 USA;

    SUNY Stony Brook Dept Biomed Engn Stony Brook NY 11794 USA;

    SUNY Stony Brook Dept Biomed Engn Stony Brook NY 11794 USA;

    SUNY Stony Brook Dept Biomed Engn Stony Brook NY 11794 USA;

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  • 原文格式 PDF
  • 正文语种 eng
  • 中图分类 化学;
  • 关键词

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