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Mapping the Surface Groups of Amine-Rich Carbon Dots Enables Covalent Catalysis in Aqueous Media
Chem ( IF 19.1 ) Pub Date : 2020-09-10 , DOI: 10.1016/j.chempr.2020.08.009
Giacomo Filippini , Francesco Amato , Cristian Rosso , Giulio Ragazzon , Alberto Vega-Peñaloza , Xavier Companyó , Luca Dell’Amico , Marcella Bonchio , Maurizio Prato

Carbon nanodots stand as the missing link between the molecular and the nanoscale world, owing to the unique molecular-like behavior emerging from their synthetic precursors. A converging set of analytical and spectroscopic data yields a precise inventory of the surface reactive groups of amine-rich carbon dots (NCDs-1). As a result, NCDs-1 provide a multi-functional nano-platform that is able to covalently activate carbonyl groups, form iminium-ions and enamine intermediates, and efficiently promote diverse aminocatalytic transformations in water. Remarkably, the catalytic activity of carbon dots can also govern the stereoselectivity in the bond-forming event. Indeed, the use of chiral carbon dots (NCDs-7) as catalysts affords the final aldol products with significant enantiomeric excess. The successful implementation of carbon nanostructures into chemical roles so far restricted to molecular systems opens new avenues for advanced applications where the nanoscale and the molecular realms will merge and complement each other.



中文翻译:

映射富含胺的碳点的表面基团可以在水性介质中进行共价催化

碳纳米点是分子与纳米尺度世界之间缺失的联系,这是由于其合成前体所表现出的独特的类分子行为。一组汇总的分析和光谱数据可得出富含胺的碳点(NCD -1)的表面反应性基团的精确清单。结果,NCD -1提供了一种多功能的纳米平台,该平台能够共价活化羰基,形成亚胺离子和烯胺中间体,并有效地促进水中的多种氨基催化转化。显着地,碳点的催化活性还可以控制键形成事件中的立体选择性。确实,使用手性碳点(NCDs- 7)作为催化剂可得到具有大量对映体过量的最终的醇醛产物。迄今为止,碳纳米结构成功地实现了化学作用,仅局限于分子系统,这为纳米级和分子领域将融合并互补的先进应用开辟了新途径。

更新日期:2020-11-06
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