Pd/Cu-cocatalyzed multi-site functionalization of in-situ generated alkenes toward carbazole-based aggregation-induced emission luminogens

IF 15.7 1区化学 Q1 CHEMISTRY, APPLIED

Chinese Journal of Catalysis Pub Date : 2025-02-01 DOI:10.1016/S1872-2067(24)60164-6

Meiqi Zhang , Xueyuan Yan , Zheng Liu , Hongyuan Bai , Hongwei Ma , Genping Huang , Bo Zhang , Dezhu Xu , Wenjia Han , Li Han , Tenglong Guo

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引用次数: 0

Abstract

In contrast to the predominant mono or difunctionalization of alkenes, the multi-site functionalization of alkenes involving the synergistic formation of more than two new C–C or C–X bonds is much challenging, especially for developing new reaction pathway to afford the functional heterocycle compounds with aggregation-induced emission (AIE) property has been rarely reported. In present work, the multi-site functionalization of in situ generated alkenes with indoles has been developed for the synthesis of diversely functionalized carbazoles through the synergistic construction of multiple C–C bonds and C=O bond. A proposed reaction sequence involving C–H alkenylation/radical oxygen atom transfer/Diels-Alder cycloaddition/dehydrogenative aromatization was supported by experiments and density functional theory calculations. Further derivative carbazole-linked-quinoxaline skeletons represent a class of AIEgens with acceptor-donor-acceptor configuration, which generated the desired twisted intramolecular charge transfer (TICT) AIE properties and could be used as fluorescent probes for detecting the micrometer-sized phase separation of polymer blends. The protocol provides a concise route for the synthesis and application of carbazole-based AIE luminogens.

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Pd/ cu共催化原位生成的烯烃向咔唑基聚集诱导发射发光物质的多位点功能化

与烯烃主要的单官能化或双官能化相比，烯烃的多官能化涉及两个以上新的C-C或C-X键的协同形成是非常具有挑战性的，特别是在开发新的反应途径以提供具有聚集诱导发射（AIE）性质的功能杂环化合物方面很少有报道。本研究发展了原位生成烯烃与吲哚的多位点功能化，通过多个C - C键和C=O键的协同构建，合成了多种功能化的咔唑。实验和密度泛函理论计算支持了C-H烷基化/自由基氧原子转移/Diels-Alder环加成/脱氢芳构化的反应顺序。进一步衍生的咔唑-喹啉骨架代表了一类具有受体-给体-受体构型的AIEgens，它产生了所需的扭曲分子内电荷转移（TICT） AIE特性，可以用作检测微米级聚合物共混物相分离的荧光探针。该方案为咔唑类AIE发光物质的合成和应用提供了一条简明的途径。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Chinese Journal of Catalysis 工程技术-工程：化工

CiteScore

25.80

自引率

10.30%

发文量

235

审稿时长

1.2 months

期刊介绍： The journal covers a broad scope, encompassing new trends in catalysis for applications in energy production, environmental protection, and the preparation of materials, petroleum chemicals, and fine chemicals. It explores the scientific foundation for preparing and activating catalysts of commercial interest, emphasizing representative models.The focus includes spectroscopic methods for structural characterization, especially in situ techniques, as well as new theoretical methods with practical impact in catalysis and catalytic reactions.The journal delves into the relationship between homogeneous and heterogeneous catalysis and includes theoretical studies on the structure and reactivity of catalysts.Additionally, contributions on photocatalysis, biocatalysis, surface science, and catalysis-related chemical kinetics are welcomed.