A colorimetric and fluorescent probe for fluoride ions based on 6‐acetyl‐2‐naphthol

Abstract

A colorimetric and turn-on fluorescent probe for fluoride ions, tert-butyldimethylsilane 6-acetyl-2-naphtholate, was readily synthesized from 6-acetyl-2-naphthol and tert-butyldimethylchlorosilane (TBSCl). The probe exhibits high sensitivity and good selectivity for fluoride ions in acetonitrile. The inherent mechanism involves the cleavage of the Si-O bond in the probe, which induced yellow color formation and prominent fluorescence enhancement.

Visualizing Fluoride Ion in Mitochondria and Lysosome of Living Cells and in Living Mice with Positively Charged Ratiometric Probes

“…In the past decade, several fluorescent probes for detection of fluoride ion were developed in solution or cell imaging [15][16][17] . They are mainly based on fluoridehydrogen bonding 18-20 , boron-fluoride or stibium-fluoride complexation [21][22][23][24] , and desilylation [25][26][27][28][29][30][31][32][33][34][35][36][37][38][39] . However, most fluorescent probes for fluoride ion still have some limitations in detection and bioimaging.…”

“…By contrast, fluorescence sensing is a powerful technology to study fluoride ion in biological systems, even in living animals. In the past decade, several fluorescent probes for detection of fluoride ion were developed in solution or cell imaging. − They are mainly based on fluoride-hydrogen bonding, − boron-fluoride or stibium-fluoride complexation, − and desilylation. − However, most fluorescent probes for the fluoride ion still have some limitations in detection and bioimaging. First, some probes could only detect tetrabutylammonium fluoride (TBAF) salt in organic or organo-aqueous solvents rather than sodium fluoride (NaF) in aqueous solutions, which limits their further applications in biological systems.…”

New Progress in the Design, Synthesis and Application of Fluorescent Probes for Fluoride Ion Detection

“…各种基于荧光酚类化合物释放而应用于氟离子检 测的探针报道还有很多. 例如, Akkaya 等 [85] 合成了探针 58 (Scheme 17), 在其 DMSO 溶液中加入 F -时, 随着 TBDMS 的脱去和二氧杂环丁烷结构的裂解, 能发出明 亮的蓝色荧光; 而宋相志等 [86] 设计合成了基于 6-乙酰 基-2-萘酚的 "turn-on" 型 F -荧光探针 59 (Scheme 18), 检 测限可达 4×10 -8 mol/L, 响应时间为 3 min. 利用各种水杨醛衍生物构建 TBDMS 类的氟离子探 针也很常见, 而且其作用机理中涉及进一步的成环反 应.…”

Recent progress in the development of fluorescent probes for hydrazine

“…Alternatively, analytical techniques based on fluorescence sensor systems are very popular because fluorescence measurements are usually easy to perform, inexpensive, very sensitive (parts per billion/trillion) with detection limits as low as sub‐parts‐per million, and able to be employed for in situ and in vivo monitoring . Hydrazine can act as a good nucleophile for a variety of transformations in synthetic chemistry, such as hydrazone formation, Wolff–Kishner reduction, heterocyclic chemistry, deprotection of phthalimides and so on.…”