A supramolecular dimer strategy for enhancing the selective generation of sulfides and sulfoxides by visible-light induced photoredox thiol-ene cross-coupling reactions of anthraquinone

IF 4.6 1区化学 Q1 CHEMISTRY, ORGANIC Organic Chemistry Frontiers Pub Date : 2024-10-03 DOI:10.1039/d4qo01454e

Fa-Dong Wang, Kaikai Niu, Shengsheng Yu, Hui Liu, Ling-Bao Xing

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Abstract

Enhancing the photocatalytic efficiency of organic photocatalysts and increasing the generation capacity of reactive oxygen species (ROS) have consistently been substantial obstacles. In this study, we designed and synthesized a supramolecular dimer based on anthraquinone (Amvp-CB[8]) between the methylated vinylpyridinium substituted anthraquinone derivative (Amvp) and cucurbit[8]uril (CB[8]) through host-guest interactions in the aqueous solution. Compared to the monomer Amvp, the supramolecular dimer Amvp-CB[8] exhibited significantly enhanced fluorescence and demonstrated remarkable capabilities in generating singlet oxygen (1O2) and superoxide anion radicals (O2•−) in water. Importantly, Amvp-CB[8] displayed superior photocatalytic activity under visible light, facilitating efficient photoredox thiol-ene cross-coupling reactions between phenthiol and styrene, which selectively enabled rapid synthesis of sulfides within 0.5 h and sulfoxides within 12 h, showcasing high efficiency, low catalyst loading, and excellent functional group tolerance. This study introduces a novel supramolecular dimer strategy that enhances the design of efficient photocatalysts for organic conversions in photocatalysis.

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通过可见光诱导的蒽醌光氧化硫醚-烯交叉偶联反应提高硫化物和硫氧化物选择性生成的超分子二聚体策略

提高有机光催化剂的光催化效率和增加活性氧（ROS）的生成能力一直是一个巨大的障碍。在本研究中，我们设计并合成了一种基于蒽醌的超分子二聚体（Amvp-CB[8]），它是甲基化乙烯基吡啶取代蒽醌衍生物（Amvp）与葫芦[8]脲（CB[8]）在水溶液中通过主客体相互作用而形成的。与单体 Amvp 相比，超分子二聚体 Amvp-CB[8] 的荧光明显增强，并在水中产生单线态氧（1O2）和超氧阴离子自由基（O2--）方面表现出卓越的能力。重要的是，Amvp-CB[8] 在可见光下显示出卓越的光催化活性，促进了苯硫酚与苯乙烯之间高效的光氧化硫酚-烯交叉偶联反应，在 0.5 小时内选择性地实现了硫化物的快速合成，在 12 小时内实现了硫氧化物的快速合成，显示出高效、低催化剂负载和优异的官能团耐受性。本研究介绍了一种新型超分子二聚体策略，有助于设计光催化有机转化的高效光催化剂。

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来源期刊

Organic Chemistry Frontiers CHEMISTRY, ORGANIC-

CiteScore

7.90

自引率

11.10%

发文量

686

审稿时长

1 months

期刊介绍： Organic Chemistry Frontiers is an esteemed journal that publishes high-quality research across the field of organic chemistry. It places a significant emphasis on studies that contribute substantially to the field by introducing new or significantly improved protocols and methodologies. The journal covers a wide array of topics which include, but are not limited to, organic synthesis, the development of synthetic methodologies, catalysis, natural products, functional organic materials, supramolecular and macromolecular chemistry, as well as physical and computational organic chemistry.