Subcellular organelle-specific probes, including mitochondria-targeted fluorescent probes, have attracted enormous research interests because they can monitor or visualize the morphology or biological activities of specific organelles and play an indispensable role in disease diagnosis. To follow the process, highly specific and photostable fluorescent probes are in demand. However, commercially available mitochondria probes normally suffer from poor photostability under laser irradiation and aggregation caused quenching (ACQ) in the aggregate state. In this work, two simple aggregation-induced emission(AIE)-active meso-2-ketopyrrolyl BODIPYs were developed via a convenient one-pot synthetic procedure from 2-methylpyrrole and corresponding pyrrolyldiketone in the presence of BF₃·OEt₂. The two AIE luminogens (AIEgens) both show very weak fluorescence (maximum emission peaks at 545 and 559 nm, respectively) in DMSO and strong near-infrared solid-state emission. The fluorescence was dramatically intensified and redshifted to 635 and 643 nm, respectively, when water fraction was increased up to above 95% in the DMSO/water mixtures. Both AIEgens were found to specifically “light up” the cell mitochondria with high biocompatibility. Interestingly, the staining process can be shortened for less than a minute after the addition of the AIEgens and without the involvement of a washing procedure, indicating an ultrafast and easy-to-operate staining protocol. Furthermore, their fluorescent images in deep tissue penetration were captured with a satisfied signal-to-noise ratio at a depth of 20 and 30 μm along the direction of the z-axis. Importantly, both AIEgens exhibit high photostability under harsh continuous laser irradiation, demonstrating their potential application as in visualizing and tracking specific mitochondria-associated dynamic changes.

亚细胞器特异性探针，包括针对线粒体的荧光探针，已经引起了巨大的研究兴趣，因为它们可以监测或可视化特定细胞器的形态或生物学活性，并且在疾病诊断中起着不可或缺的作用。为了遵循该过程，需要高度特异性和耐光的荧光探针。但是，市售的线粒体探针通常在激光辐照下具有较差的光稳定性，并且在聚集状态下会引起聚集引起的猝灭（ACQ）。在这项工作中，通过在BF存在下由2-甲基吡咯和相应的吡咯基二酮通过便捷的一锅合成方法开发了两个简单的聚集诱导发射（AIE）-活性内消旋-2-酮基吡咯烷基BODIPYs₃ ·OEt ₂。两种AIE发光剂（AIEgens）都在DMSO中显示出非常弱的荧光（分别在545和559 nm处具有最大发射峰）和强大的近红外固态发射。当在DMSO /水混合物中水含量增加到95％以上时，荧光显着增强，分别红移至635和643 nm。发现这两种AIEgens都以高生物相容性特异性“点亮”细胞线粒体。有趣的是，在添加AIEgens之后，染色过程可以缩短不到一分钟，而且无需洗涤程序，这表明染色过程超快且易于操作。此外，沿z轴方向在深度为20和30μm处以令人满意的信噪比捕获了深部组织穿透中的荧光图像。