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Molecularly Imprinted Polymer as an Eco-Compatible Nanoreactor in Multicomponent Reactions: A Remarkable Synergy for Expedient Access to Highly Substituted Imidazoles
ACS Sustainable Chemistry & Engineering ( IF 8.4 ) Pub Date : 2017-09-18 00:00:00 , DOI: 10.1021/acssuschemeng.7b02741
Ahmad Shaabani 1 , Ronak Afshari 1 , Seyyed Emad Hooshmand 1 , Mina Keramati Nejad 1
Affiliation  

In this paper, an eco-compatible molecularly imprinted polymer (MIP) nanoreactor synthesized via miniemulsion polymerization was designed, and its catalytic activity was investigated in multicomponent reaction transformations for the first time. The synthesized MIP nanoreactor was characterized by means of Fourier transform infrared, thermogravimetric analysis, differential scanning calorimetry, scanning electron microscopy, transmission electron microscopy, and dynamic light scattering. The imidazole template-derived sites created within a polymeric matrix allow MIP nanoreactors to directly catalyze the reaction and conduct the target molecule. The results show the applicability of MIP nanoreactors in a one-pot expeditious synthesis of tri- and tetrasubstituted imidazole derivatives via pseudo-four- and four-component reactions with excellent yields and purities. In addition, biocompatibility and cytotoxicity of MIP nanoparticles were examined, and no obvious adverse effects on the viability of human fibroblast cells were observed. This green and facile catalytic route has an easy setup, and the products are easily isolated without tedious purification such as aqueous workup or chromatography in high purity. Meanwhile, MIP nanoreactors showed admirable potential in reusable catalysis, being recycled for several runs without losing significant activities.The MIP nanoreactor utilization strategy can be extended to the other multicomponent reactions leading to manifold pharmaceutical and environmental applications.

中文翻译:

分子印迹聚合物在多组分反应中作为生态兼容的纳米反应器:显着的协同作用,可方便地获得高度取代的咪唑

本文设计了一种通过细乳液聚合法合成的生态相容性分子印迹聚合物(MIP)纳米反应器,并首次在多组分反应转化中研究了其催化活性。合成的MIP纳米反应器通过傅里叶变换红外光谱,热重分析,差示扫描量热法,扫描电子显微镜,透射电子显微镜和动态光散射进行了表征。在聚合物基质中产生的咪唑模板衍生位点允许MIP纳米反应器直接催化反应并进行目标分子。结果表明,MIP纳米反应器可通过假四-和四-组分反应以优异的收率和纯度一锅快速合成三和四取代的咪唑衍生物。另外,检查了MIP纳米颗粒的生物相容性和细胞毒性,未观察到对人成纤维细胞活力的明显不利影响。这种绿色,便捷的催化路线易于设置,无需繁琐的纯化(如水后处理或高纯度色谱法)即可轻松分离出产物。同时,MIP纳米反应器在可重复使用的催化方面显示出令人赞叹的潜力,可以循环使用几次,而不会损失任何重要的活性。
更新日期:2017-09-19
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