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通过芳基腈进行复杂介导的亲核芳香取代反应,以实现用于生物成像的分子内摆动受限的D-A型聚集诱导发光体。

Complex-mediated nucleophilic aromatic substitution with aryl nitriles to realize intramolecular flapping-restricted D-A AIEgens for bioimaging.

作者信息

Liu Feng, Liu Junkai, Gong Junyi, Lin Runfeng, Qiu Siyuan, Liu Zicheng, Li Chongyang, Meng Miao, Li Shijie, Tu Mei, Lam Jacky W Y, Niu Guangle, Chen Ming

机构信息

College of Chemistry and Materials Science Jinan University Guangzhou China.

Department of Chemistry Hong Kong Branch of Chinese National Engineering Research Center for Tissue Restoration and Reconstruction The Hong Kong University of Science and Technology Kowloon Hong Kong China.

出版信息

Smart Mol. 2024 Nov 14;3(2):e20240039. doi: 10.1002/smo.20240039. eCollection 2025 Jun.

DOI:10.1002/smo.20240039
PMID:40671928
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC12262011/
Abstract

Donor-acceptor (D-A) compounds are particularly important in optoelectronic and biological applications. However, they are normally synthesized in the presence of transition metal catalysts. Herein, we report a metal-free method by a complex-mediated nucleophilic aromatic substitution of aryl nitriles with amines. The method can lead to rich D-A type aggregation-induced emission luminogens (AIEgens) with tunable properties. They emit from deep-blue to yellow-green and possess high photoluminescence quantum yields up to 70.5% in the aggregate state. Interestingly, the suppression of intramolecular flapping is proved to play an indispensable role in the AIE behavior, which is different from the mechanism met in other AIEgens. Moreover, the biocompatible AIEgens possess specific staining of lipid droplets in HeLa cells and the superiority of identifying fatty liver over traditional Oil Red O staining is exhibited.

摘要

供体-受体(D-A)化合物在光电和生物应用中尤为重要。然而,它们通常是在过渡金属催化剂存在的情况下合成的。在此,我们报道了一种无金属方法,通过络合物介导的芳基腈与胺的亲核芳香取代反应来实现。该方法能够产生具有可调性质的丰富的D-A型聚集诱导发光发光体(AIEgens)。它们发射从深蓝色到黄绿色的光,并且在聚集态下具有高达70.5%的高光致发光量子产率。有趣的是,分子内摆动的抑制被证明在AIE行为中起着不可或缺的作用,这与其他AIEgens中遇到的机制不同。此外,生物相容性AIEgens对HeLa细胞中的脂滴具有特异性染色,并且展现出相较于传统油红O染色在识别脂肪肝方面的优势。

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