Synthesis of Copolymers from Phenylboronic Acid-Installed Cyclic Carbonates
Synthesis of Copolymers from Phenylboronic Acid-Installed Cyclic Carbonates
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DOI：
10.1021/mz500047p
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发表时间：
2014-04-01
影响因子：
7.015
通讯作者：
Herrera-Alonso, Margarita
中科院分区：
文献类型：
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作者：
Aguirre-Chagala, Yanet Elised;Santos, Jose Luis;Herrera-Alonso, Margarita
有机硼聚合物在生物医学应用中起着重要作用。大量含硼酸衍生物的单体已被合成，尤其侧重于可控自由基聚合方法。通过开环聚合（ROP）途径合成的有机硼聚合物的研究则少得多。我们报道了从聚（乙二醇）大分子引发剂出发，由DBU催化含硼酸的环状碳酸酯的开环聚合。可控聚合能达到相对较高的转化率（约70%）且多分散性较低。通过用游离的二硼酸置换保护基，很容易实现共聚物脱保护以生成硼酸侧基。所得的两亲性共聚物在水中自组装成球形纳米粒子或囊泡，这取决于亲水/疏水比例。我们设想这些功能性碳酸酯可直接应用于生物可降解两亲性组装体的核稳定，或用于药物和蛋白质包封。
Organoboron polymers play important roles in biomedical applications. An ample number of monomers bearing boronic acid derivatives have been synthesized, particularly focusing on controlled free radical polymerization methods. Organoboron polymers synthesized by ring-opening polymerization (ROP) routes are far less explored. We report on the ROP of boronic acid-installed cyclic carbonates, catalyzed by DBU from a poly(ethylene glycol) macroinitiator. Controlled polymerization proceeded to relatively high conversions (similar to 70%) with low polydispersity. Deprotection of the copolymer to generate the boronic acid pendant group was readily achieved by displacement of the protecting group with free diboronic acid. The resulting amphiphilic copolymers self-assembled in water into spherical nanoparticles or vesicles, depending on hydrophilic/hydrophobic ratio. We envision these functional carbonates finding direct applications for core stabilization of biodegradable amphiphilic assemblies or in drug and protein encapsulation.