Yu Changjiang, Di Guangyuan, Li Qian, Guo Xing, Wang Lei, Gong Qingbao, Wei Yaxiong, Zhao Quansheng, Jiao Lijuan, Hao Erhong
Anhui Laboratory of Molecule-Based Materials; The Key Laboratory of Functional Molecular Solids, Ministry of Education, School of Chemistry and Materials Science; Anhui Province Key Laboratory of Optoelectrical Materials Science and Technology, School of Physics and Electronic Information, Anhui Normal University, Wuhu, Anhui 241002, China.
The First Affiliated Hospital/Yijishan Hospital of Wannan Medical College; Institutes of Brain Science, Wannan Medical College, Wuhu 241001, China.
Inorg Chem. 2024 Nov 11;63(45):21397-21409. doi: 10.1021/acs.inorgchem.4c03194. Epub 2024 Oct 31.
Fluorescent molecular platforms are highly sought after for their applications in biology and optoelectronics but face challenges with solid-state emission quenching. To address this, bulky substituents or aggregation-induced emission luminogens to restrict intramolecular motion are used to enhance the brightness. Here, we have successfully engineered a novel class of boron complexed pyrrolide salicyl-hydrazone fluorophores named BPSHY. These dyes were synthesized through a diversity-oriented condensation of pyrrole and salicylaldehyde derivatives combined with various aromatic boronic acids. The resulting 3D structures, owing to bulky boron axially substituted aryl groups, impart excellent solubility in a variety of solvents. Significantly, the BPSHY dyes exhibit strong absorption in the visible region and remarkably large Stokes shifts. Crucially, they demonstrate intense emission in aqueous solutions due to aggregation-induced emission effects. In solid-states, these dyes achieve high quantum yields, reaching up to 58%. Further expanding their utility, we developed two new BPSHY probes: one incorporating morpholine and another containing triphenylphosphine salt. Both of them are found to specifically label subcellular organelles such as lysosomes and mitochondria within live cells. Notably, these probes demonstrate exceptional staining efficacy and two-photon fluorescence feature. This highlights the considerable promise of BPSHY fluorophores for monitoring and visualizing the dynamic transformations of organelles.
荧光分子平台因其在生物学和光电子学中的应用而备受追捧，但面临固态发射猝灭的挑战。为了解决这一问题，人们使用体积庞大的取代基或聚集诱导发光发光体来限制分子内运动，以提高亮度。在此，我们成功设计了一类新型的硼络合吡咯水杨腙荧光团，命名为BPSHY。这些染料是通过吡咯和水杨醛衍生物与各种芳基硼酸的多样性导向缩合反应合成的。由于体积庞大的硼轴向取代芳基基团，所得的三维结构在各种溶剂中具有优异的溶解性。值得注意的是，BPSHY染料在可见光区域表现出强烈的吸收，并且具有显著大的斯托克斯位移。至关重要的是，由于聚集诱导发光效应，它们在水溶液中表现出强烈的发射。在固态下，这些染料实现了高达58%的高量子产率。为了进一步扩展其用途，我们开发了两种新的BPSHY探针：一种含有吗啉，另一种含有三苯基膦盐。发现它们都能特异性标记活细胞内的亚细胞器，如溶酶体和线粒体。值得注意的是，这些探针表现出优异的染色效果和双光子荧光特性。这突出了BPSHY荧光团在监测和可视化细胞器动态变化方面的巨大潜力。
