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构建 2-叠氮基乙酸功能化高结晶度荧光共价有机骨架:米托蒽醌和 Fe 传感与吸附应用。

Construction of 2-azidacetic acid functionalized high-crystallinity fluorescent covalent organic framework: Applications in mitoxantrone and Fe sensing and adsorption.

机构信息

School of Pharmacy, Southwest Medical University, Luzhou, Sichuan, China.

Sichuan College of Traditional Chinese Medicine, Mianyang, Sichuan, China.

出版信息

Chemosphere. 2024 Oct;366:143498. doi: 10.1016/j.chemosphere.2024.143498. Epub 2024 Oct 9.

Abstract

Due to the dual functions of fluorescence detection and adsorption, fluorescent covalent organic frameworks (COFs) have attracted significant attention. However, common fluorescent COFs often exhibit unsatisfactory fluorescence properties and selectivity, coupled with poor solution dispersibility, which limit their effectiveness in detection and adsorption applications. In response, a novel post-modified fluorescent COF (named AZC-COF) was synthesized by connecting a fluorescent COF (COF-TB) with 2-azidacetic acid through a copper-catalyzed aide-alkyne cycloaddition (CuAAC) reaction. AZC-COF demonstrated excellent solution dispersibility and robust green fluorescence, boasting an absolute fluorescence quantum yield (QY) of 7.58%, which was 13.5 times higher than that of COF-TB. Furthermore, leveraging the active carboxylic acid and triazole sites, AZC-COF exhibited remarkable binding abilities for mitoxantrone (MIX) and Fe, enabling sensitive detection and efficient adsorption of them. In contrast, due to the absence of these functional sites, COF-TB showed poor detection and enrichment capabilities for MIX and Fe. The impressive detection and adsorption efficiencies of MIX and Fe in environmental water, aquatic organism (fish) and plasma samples underscore the potential of AZC-COF as a detection-adsorption platform. Additionally, AZC-COF demonstrated low toxicity and hemolytic activity, alongside promising potential for cell imaging and detection of MIX and Fe, highlighting its considerable application prospect in biological systems.

摘要

由于荧光检测和吸附的双重功能,荧光共价有机骨架(COFs)引起了人们的极大关注。然而,常见的荧光 COFs 通常表现出不尽如人意的荧光性质和选择性,加上较差的溶液分散性,限制了它们在检测和吸附应用中的效果。有鉴于此,通过铜催化的叠氮化物-炔烃环加成(CuAAC)反应,将荧光 COF(COF-TB)与 2-叠氮乙酸连接,合成了一种新型的后修饰荧光 COF(命名为 AZC-COF)。AZC-COF 表现出优异的溶液分散性和强的绿色荧光,其绝对荧光量子产率(QY)为 7.58%,比 COF-TB 高 13.5 倍。此外,利用活性羧酸和三唑基团,AZC-COF 对米托蒽醌(MIX)和 Fe 表现出显著的结合能力,能够对它们进行敏感检测和高效吸附。相比之下,由于缺乏这些功能基团,COF-TB 对 MIX 和 Fe 的检测和富集能力较差。在环境水、水生生物(鱼)和血浆样品中对 MIX 和 Fe 的出色检测和吸附效率突显了 AZC-COF 作为检测-吸附平台的潜力。此外,AZC-COF 表现出低毒性和溶血活性,以及对 MIX 和 Fe 的细胞成像和检测的良好应用前景,这凸显了其在生物系统中相当大的应用前景。

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