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一锅法磁性氧化铁-碳纳米点复合材料在叔丁基过氧化氢存在下催化喹唑啉酮的环氧化水相串联合成。

One-Pot Magnetic Iron Oxide-Carbon Nanodot Composite-Catalyzed Cyclooxidative Aqueous Tandem Synthesis of Quinazolinones in the Presence of -Butyl Hydroperoxide.

作者信息

Majumdar Biju, Sarma Daisy, Jain Siddarth, Sarma Tridib K

机构信息

Discipline of Chemistry, Indian Institute of Technology Indore, Simrol, Khandwa Road, Indore 453552, Madhya Pradesh, India.

出版信息

ACS Omega. 2018 Oct 19;3(10):13711-13719. doi: 10.1021/acsomega.8b01794. eCollection 2018 Oct 31.

Abstract

The development of synthetic protocols for biologically important molecules using biocompatible catalysts in aqueous medium holds the key in green and sustainable chemistry. Herein, a magnetically recoverable iron oxide-carbon dot nanocomposite has been demonstrated as an effective catalyst for cyclooxidative tandem synthesis of quinazolinones in aqueous medium using alcohols as starting materials. Fluorescent carbon dots, the newest entrant in the nanocarbon family, were used as the stabilizing agent for the iron oxide nanoparticles, and a continuous layer of carbon dots decorates the iron oxide nanoparticle surface as observed by transmission electron microscopy. The fluorescence studies demonstrated the effective electron transfer from carbon dots to the iron oxide nanoparticles resulting in complete quenching of emission owing to carbon dots, once it binds with iron oxide nanoparticles. The nanocatalyst showed high activity with significant reusability for the syntheses of quinazolinones in the presence of -butyl hydroperoxide (TBHP) in an aqueous medium. Controlled experiments revealed the synergistic effect of carbon dots in enhancing the catalytic activity of iron oxide, as they might influence the decomposition of TBHP into radicals owing to their peroxidase activity. These radicals stabilized over the nanoparticle surface are known to have increased lifetime compared to solution-based radicals. These surface-stabilized radicals then could catalyze the tandem reaction resulting in the formation of the quinazolinone derivatives in high yields.

摘要

在水介质中使用生物相容性催化剂开发具有生物学重要性的分子的合成方案是绿色和可持续化学的关键所在。在此,一种可磁回收的氧化铁-碳点纳米复合材料已被证明是一种有效的催化剂,可在水介质中以醇为起始原料进行喹唑啉酮的环氧化串联合成。荧光碳点是纳米碳家族中的最新成员,用作氧化铁纳米颗粒的稳定剂,并且如通过透射电子显微镜观察到的,连续的碳点层装饰在氧化铁纳米颗粒表面。荧光研究表明,一旦碳点与氧化铁纳米颗粒结合,就会发生从碳点到氧化铁纳米颗粒的有效电子转移,导致碳点的发射完全猝灭。该纳米催化剂在水介质中存在叔丁基过氧化氢(TBHP)的情况下,对喹唑啉酮的合成表现出高活性和显著的可重复使用性。对照实验揭示了碳点在增强氧化铁催化活性方面的协同作用,因为它们可能由于过氧化物酶活性而影响TBHP分解为自由基。已知这些在纳米颗粒表面稳定的自由基与基于溶液的自由基相比具有更长的寿命。然后这些表面稳定的自由基可以催化串联反应,从而高产率地形成喹唑啉酮衍生物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/cf00/6644479/6fc4c5bf19fc/ao-2018-01794u_0004.jpg

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