In the present paper, a novel difluoroboron dipyrromethene-based (BODIPY) fluorescent probe with a conjugated hydrazone group, named BDBH, was developed for the detection of F⁻ with high selectivity and sensitivity. After addition of tetrabutylammonium fluoride (TBAF) into a BDBH solution, the fluorescence was “turned on”, which displayed an 80-fold increasement of emission intensity. The wavelengths of excitation and emission were 518 nm and 613 nm respectively, which were free from the background interference. The titration of ¹H NMR (Nuclear Magnetic Resonance) indicated that the interaction involved hydrogen-bonding formation between the acidic H of -NH-C=O group and F⁻ at low concentration and deprotonation of N-H group at increasing concentration of fluoride. The theoretical calculations verified that once F⁻ interacted with BDBH, the planarity and conjugation of BDBH enhanced, which resulted in a strong fluorescence emission at 613 nm. Furthermore, confocal fluorescence images of BDBH-incubated HeLa cells verified its potential application as an “off-on” sensor to monitor F¯ in living cells.

在本文件中，一种新颖的基于difluoroboron二吡咯亚甲基- （BODIPY）荧光与共轭腙基，命名为BDBH探针时，用于检测的F开发^-高选择性和灵敏度。将四丁基氟化铵（TBAF）添加到BDBH溶液中后，荧光“打开”，显示出发射强度增加了80倍。激发和发射的波长分别为518 nm和613 nm，没有背景干扰。的滴定¹ 1 H NMR（核磁共振）表明，-NH-C =的酸性H 2 O组和F之间的相互作用参与氢键形成^-在低浓度下，在氟化物浓度增加时，NH基团会去质子化。理论计算证实一旦˚F ^-相互作用与BDBH，平面性和BDBH的缀合增强，这导致在613纳米的强的荧光发射。此外，BDBH孵育的HeLa细胞的共聚焦荧光图像证明了其潜在的应用作为“活着的”传感器来监测活细胞中的F。