Abstract
We have synthesized novel coumarin-based fluorescent chemosensors for detection of fluoride ions in aqueous solution. The detection mechanism relied on a fluoride-mediated desilylation triggering fluorogenic reaction and a strong interaction between fluoride and the silicon center. In this work, the hydroxyl-decorated coumarins containing oxysilyl moiety have been synthesized through the aldehyde-functionalized coumarins. The optical responses toward fluoride, as well as aqueous stability studies of both aldehyde and hydroxyl functionalized coumarins, have been investigated. Due to the highest fluorescence enhancement upon the addition of fluoride and good stability in aqueous solution, the hydroxyl-decorated coumarin connected with the bulky tert-butyldiphenyloxysilyl group (-OSitBuPh2) has been selected for further investigation of its potential as a fluoride sensor. This hydroxyl-decorated coumarin can selectively sense fluoride ions in aqueous media (contain 0.8% MeCN) with desirable response times (40 min). The limit of detection of this compound was determined as 0.043 ppm, satisfying the standard fluoride level (0.7 ppm) in drinking water recommended by U.S. Department of Health and Human Services. The application of this silyl-capped coumarin derivative for fluoride analysis in collected water samples displayed satisfactory analytical accuracy (<5% error). Finally, this compound was successfully employed in fluorescence bioimaging of fluoride ions in human liver cancer cells, indicating its excellent cell permeability, ability to retain inside the living cells, and good stability under physiological conditions.
Highlights
The fluoride ion (F− ) is of special interest owing to its important role in tooth decay prevention [1], osteoporosis treatment [2], and medical diagnosis by positron emission tomography (PET) [3,4,5,6].overexposure to fluoride can lead to adverse health effects, such as dental/skeletal fluorosis, and acute gastric and kidney problems, because fluoride is readily absorbed by the human body, but is excreted slowly [7,8,9]
Hydroxyl-decorated coumarins containing oxysilyl moiety (4 and 5) were synthesized through aldehyde-functionalized coumarin intermediates (2 and 3) (Scheme 1)
We have synthesized new coumarin-based fluorescent probes for fluoride detection relying on a fluoride-promoted desilylation triggering fluorogenic reaction in aqueous media
Summary
The fluoride ion (F− ) is of special interest owing to its important role in tooth decay prevention [1], osteoporosis treatment [2], and medical diagnosis by positron emission tomography (PET) [3,4,5,6].overexposure to fluoride can lead to adverse health effects, such as dental/skeletal fluorosis, and acute gastric and kidney problems, because fluoride is readily absorbed by the human body, but is excreted slowly [7,8,9]. High fluoride levels in drinking water have been linked to neurodevelopmental disabilities in children [10] These detrimental health effects have sparked growing attention in the development of fluoride sensors at part-per-million (ppm) levels in aqueous phase and biological systems. Several fluoride-sensing platforms have been demonstrated, only a few examples including dyes decorated with methyl ester [27], ammonium [26], and polyethylene glycol (PEG) [21], can be employed in the purely aqueous phase These findings indicated that the introduction of hydrophilic moieties into dyes could improve their hydrophilicity, and enhance their capability to detect fluoride ions in 100% water
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