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Surface- and Redox-Active Multifunctional Polyphenol-Derived Poly(ionic liquid)s: Controlled Synthesis and Characterization
Macromolecules ( IF 5.1 ) Pub Date : 2016-09-30 00:00:00 , DOI: 10.1021/acs.macromol.6b01857
Nagaraj Patil 1 , Daniela Cordella 1 , Abdelhafid Aqil 1 , Antoine Debuigne 1 , Shimelis Admassie 2, 3 , Christine Jérôme 1 , Christophe Detrembleur 1
Affiliation  

Combining the redox activity and remarkable adhesion propensity of polyphenols (such as catechol or pyrogallol) with the numerous tunable properties of poly(ionic liquid)s (PILs) is an attractive route to design inventive multifunctional macromolecular platforms. In this contribution, we describe the first synthesis of a novel family of structurally well-defined PILs functionalized with catechol/pyrogallol/phenol pendants by organometallic-mediated radical polymerization (OMRP) using an alkyl–cobalt(III) complex as initiator and mediating agent. The living character of the chains is also exploited to produce di- and triblock PILs, and the facile counteranion exchange reactions afforded a library of PILs-bearing free phenol/catechol/pyrogallol moieties. Electrochemical investigations of catechol/pyrogallol-derived PILs in aqueous medium demonstrated the characteristic catechol to o-quinone transformations, whereas, quasi-reversible doping/undoping with supporting electrolyte cations (Li+/tetrabutylammonium+) has been observed in organic media, suggesting a bright future for this new family of redox-active PILs as cathode material for secondary energy storage devices. Also, pendant catechol/pyrogallol groups mediated sustained anchoring onto the gold surface conferred PILs properties to the interface. As a proof-of-concept, both the adsorption and inhibition of proteins on polymer modified surfaces have been demonstrated in real time using the quartz crystal microbalance with dissipation technique. The exquisite physicochemical tunability of these innovative surface- and redox-active PILs makes them excellent candidates for a broad range of potential applications, including “smart surfaces” and electrochemical energy storage devices.

中文翻译:

具有表面活性和氧化还原活性的多功能多酚衍生聚离子液体:受控合成和表征

将多酚(例如邻苯二酚或邻苯三酚)的氧化还原活性和显着的附着力与聚(离子液体)(PIL)的众多可调特性相结合,是设计本发明的多功能大分子平台的一种有吸引力的途径。在这项贡献中,我们描述了通过烷基-钴(III)络合物作为引发剂和介导剂的有机金属介导的自由基聚合(OMRP),首次合成了具有邻苯二酚/邻苯三酚/苯酚侧基官能团的结构明确的新型PIL系列。还利用了链的活性特征来产生二嵌段和三嵌段PIL,并且容易的抗衡阴离子交换反应提供了带有PIL的游离酚/邻苯二酚/间苯三酚部分的文库。醌转化,而支持电解质阳离子(Li + /四丁基铵+)已在有机介质中观察到,这表明该新的氧化还原活性PIL系列作为二次能量存储设备的阴极材料具有广阔的前景。同样,侧基邻苯二酚/间苯三酚基团介导的持久锚定在金表面上赋予了界面PILs性质。作为概念验证,已使用耗散技术的石英晶体微天平实时证明了蛋白质在聚合物改性表面上的吸附和抑制。这些创新的具有表面活性和氧化还原活性的PIL具有出色的物理化学可调谐性,使其成为各种潜在应用(包括“智能表面”和电化学储能设备)的极佳候选者。
更新日期:2016-09-30
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