Tao Jisheng, Wang Huizhen, Sun Yue, Sun Xiaoxia, Hu Yu
Jiangxi Key Laboratory of Organic Chemistry, Jiangxi Science and Technology Normal University Nanchang 330013 China
College of Chemistry, Nanchang University Nanchang China
RSC Adv. 2024 Jan 12;14(4):2422-2428. doi: 10.1039/d3ra07654g. eCollection 2024 Jan 10.
A novel fluorescent "off" sensor, -β-d-1, was obtained in high yield (91.2%) by using octahydronaphthol as a backbone, introducing an alkyne group at the 2-position, and linking azido-glucose a click reaction. The sensor was analyzed by scanning electron microscopy and transmission electron microscopy and was found to be a self-assembled vesicle. AFM results showed that the fluorescence burst was extinguished by the addition of Fe, and the fluorescence was restored by the addition of cysteine. This is due to charge transfer within the molecular structure, resulting in the ICT effect and phototransfer of electrons (PET), as well as redshifting (from 331 nm to 351 nm) and quenching of the fluorescence. The self-assembled vesicles of the fluorescent sensor -β-d-1 encapsulated Fe, but upon addition of cysteine, the vesicles of -β-d-1-Fe were also complexed with it, forming the -β-d-1-Fe-l-Cys complex, at which point fluorescence gradually returned. Therefore, the fluorescence test of this probe showed that the lowest detection limit of iron ions was 1.67 × 10 mol L, and its complexation mode was in the form of 1 + 1. The novel probe formed by -β-d-1-Fe can be used for the fluorescence detection of cysteine.
通过使用八氢萘酚作为骨架，在2位引入炔基，并通过点击反应连接叠氮基葡萄糖，以高产率（91.2%）获得了一种新型荧光“关闭”传感器-β-d-1。通过扫描电子显微镜和透射电子显微镜对该传感器进行分析，发现它是一种自组装囊泡。原子力显微镜结果表明，添加铁会使荧光猝灭，而添加半胱氨酸后荧光恢复。这是由于分子结构内的电荷转移，导致了ICT效应和电子的光致转移（PET）以及荧光的红移（从331nm到351nm）和猝灭。荧光传感器-β-d-1的自组装囊泡包裹了铁，但加入半胱氨酸后，-β-d-1-Fe囊泡也与之络合，形成-β-d-1-Fe-l-Cys络合物，此时荧光逐渐恢复。因此，该探针的荧光测试表明铁离子的最低检测限为1.67×10 mol L，其络合模式为1+1形式。由-β-d-1-Fe形成的新型探针可用于半胱氨酸的荧光检测。
