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AIEE 活性纳米组装吡嗪基有机光敏剂作为高效无金属超分子光氧化还原催化体系。

AIEE Active Nanoassemblies of Pyrazine Based Organic Photosensitizers as Efficient Metal-Free Supramolecular Photoredox Catalytic Systems.

机构信息

Department of Chemistry, UGC Sponsored Centre for Advanced Studies-II Guru Nanak Dev University, Amritsar, 143005, Punjab, India.

出版信息

Sci Rep. 2019 Jul 31;9(1):11142. doi: 10.1038/s41598-019-47588-5.

DOI:10.1038/s41598-019-47588-5
PMID:31366949
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6668430/
Abstract

Pyrazine derivatives DIPY, TETPY and CNDIPY have been designed and synthesized which form fluorescent supramolecular assemblies in mixed aqueous media due to their AIEE and ICT characteristics. Among all the derivatives, the assemblies of TETPY and CNDIPY show strong absorption in the visible region with high absorption coefficients, low HOMO-LUMO gap, and high photostability. Further, the supramolecular nanoassemblies of TETPY and CNDIPY show excellent potential to generate reactive oxygen species (ROS) under the visible light irradiation. Owing to their strong absorption in the visible region and ROS generation ability, the supramolecular nanoassemblies of TETPY and CNDIPY act as efficient photoredox catalytic systems for carrying out (a) oxidative amidation of aromatic aldehydes (b) hydroxylation of boronic acid and (c) oxidative homocoupling of benzylamines under mild conditions such as aqueous media, aerial environment, and natural sunlight as a source of irradiation. All the mechanistic investigations suggest the participation of in-situ generated ROS in the organic transformations upon light irradiation.

摘要

吡嗪衍生物 DIPY、TETPY 和 CNDIPY 已被设计和合成，由于它们具有 AIEE 和 ICT 特性，因此在混合水介质中形成荧光超分子组装体。在所有衍生物中，TETPY 和 CNDIPY 的组装体在可见光区域显示出强吸收，具有高吸收系数、低 HOMO-LUMO 间隙和高光稳定性。此外，TETPY 和 CNDIPY 的超分子纳米组装体在可见光照射下显示出产生活性氧物种 (ROS) 的优异潜力。由于它们在可见光区域的强吸收和产生 ROS 的能力，TETPY 和 CNDIPY 的超分子纳米组装体作为有效的光还原催化体系，可在温和条件下进行（a）芳醛的氧化酰胺化、（b）硼酸的羟基化和（c）苄胺的氧化偶联，条件如水介质、空气环境和自然光作为辐射源。所有的机制研究都表明，在光照下的有机转化中，原位生成的 ROS 参与其中。

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