A TICT-active orthogonal D-A type probe phenothiazine-BODIPY for ratiometric response of hypochlorite and its application in living cells

紧身衣 光化学 荧光 吩噻嗪 化学 量子产额 接受者 滴定法 单线态氧 分子内力 溶剂 氧气 无机化学 立体化学 有机化学 凝聚态物理 物理 药理学 医学 量子力学
作者
Chengjun Wang,Ying Qian
出处
期刊:Journal of Luminescence [Elsevier]
卷期号:210: 261-268 被引量:23
标识
DOI:10.1016/j.jlumin.2019.02.044
摘要

A red emissive fluorescent probe 1,7-dimethyl-3,5-bis(4-methoxyphenyl-vinyl)-8-(10-n-butyl-10H-phenothiazine-3-yl)BODIPY 1,7-dimethyl-3,5-bis(4-methoxyphenyl-vinyl)-8-(10-n-butyl-10H-phenothiazine-3-yl)BODIPY (avyl-BODIPY-PTZ) with a special orthogonal donor-acceptor structure was designed and synthesized for rapid, sensitive, and selective discrimination of ClO−, over other reactive oxygen species and anions. The probe displays a linear ratiometric absorption (A578/A640) and fluorescence (F599/F660) response toward ClO− with a fast response velocity (~10 s). The limit of detection (LOD) for ClO− was obtained as 22.6 nM from the fluorescence titration experiment. The fluorescence enhancement of the probe can be observed from the 32-fold enhancement in ratiometric value (F599/F660) and the increasement of quantum yield from 0.01 at 660 nm to 0.28 at 599 nm. The oxidation of S atom in phenothiazine by ClO− to form the sulfoxide-type structure was proposed as the recognizing mechanism according to the Mass spectral analysis. The ratiometric enhancement of fluorescence was rationalized by the theoretical calculations. The orthogonal donor-acceptor structure according to optimized calculation and solvent effects of avyl-BODIPY-PTZ illustrated that the ClO− oxidation induced conversion from the nonradiative TICT process to the radiative LE process and caused the fluorescence ratiometric enhancement. The probe with low cytotoxity can successfully permeate into living cells and the cell images can be achieved in single channel. Moreover, after addition of ClO−, another bright red emission channel of the probe switched on and the probe displayed two-channel emission in living cells.
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