Selective fluorescence detection of fluoride using boronic acids

Cooper, Christopher R.; Spencer, Neil; James, Tony D.

doi:10.1039/a801693c

Cited by 229 publications

(108 citation statements)

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“…The results show that the present chemosensor exhibits excellent sensitivity and stability of the color for the detection of fluoride from 1.5 × 10 -5 M to 1.5 × 10 -4 M, which are very high compared to the reported methods. 1,26 Kinetic studies indicate that the reaction occurs impulsively at room temperature, whereas the method reported by Wada et al 27 needs heating the sample at 60˚C; also the color of the reaction was stable for more than two weeks.…”

Section: Naked-eye Detection Of Fluoride and Advantagesmentioning

confidence: 99%

“…1,2 However, the World Health Organization (WHO) upper limit of fluoride in drinking water is 7.9 × 10 -5 mol dm -3 , and the high levels of fluoride have caused toxicity in animals and mottled teeth in humans. Several methods, such as ion-selective electrodes (ISE), 3 colorimetry, [4][5][6][7] fluorescence [8][9][10] and capillary electrophoresis, 11 have been reported for the determination of fluoride.…”

Section: Introductionmentioning

confidence: 99%

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Naked-Eye Detection of Fluoride Using Zr(IV)-EDTA Complex and Pyrocatechol Violet

Balaji

Matsunaga

2005

ANAL. SCI.

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The use of fluoride has been increasing because of its great potential for industrial and biological applications. 1,2 However, the World Health Organization (WHO) upper limit of fluoride in drinking water is 7.9 × 10 -5 mol dm -3 , and the high levels of fluoride have caused toxicity in animals and mottled teeth in humans. Several methods, such as ion-selective electrodes (ISE), 3 colorimetry, [4][5][6][7] fluorescence [8][9][10] and capillary electrophoresis, 11 have been reported for the determination of fluoride.Among these, the chemical systems that respond to the presence of ions by color change detectable by vision are rare. 12 These chemosensors do not have any need to use a potentiostat or a spectrometer to detect redox or optical perturbations, and as a result, have substantial advantages over other molecular chemosensors. 13 Lanthanum(III), Zr(IV) and Ce(III) complexes with dye compounds have been used for the colorimetric detection of fluoride.14 These systems have a lack of chemical stability, and take a long time for color development. Supramolecular compounds, such as trianthryl borane derivatives and calix(4)pyrrole derivatives have been examined as fluoride chemosensors via strong hydrogen-bond formation. 5,15 The observed color changes in these systems take place only in organic media, but are reversed upon the addition of water. As a result, procedures for the naked-eye detection of anions in aqueous media are needed to overcome the above shortcomings.A fluoride, because of its high electro negativity, forms stable binary or ternary complexes with many trivalent and tetravalent metal ions, and even with their complexes. It has been reported that Zr-EDTA can bind fluoride as well as oxo anions of arsenic and selenium by a ligand-exchange mechanism with coordinated water. [16][17][18] Hence, the combined use of Zr(H2O)2EDTA as an anion receptor and an appropriate chromophore was expected to give a good chemosensor for the nacked-eye detection of fluoride.In the present study, we observed that PV forms a ternary complex with Zr-EDTA by replacing water molecules, and produces an intense blue color. The blue color of this system readily shifts to orange red by the addition of fluoride, along with the release of free PV.These observations have successfully allowed us to construct a chemosensor for the visual detection of fluoride in aqueous solution. Experimental ReagentsAll reagents and solvents used were of analytical reagent grade. A stock solution of fluoride (0.0526 mol dm -3 ) was prepared by dissolving 99.9% NaF (Wako, Japan) in distilled water and standardized using the Alfusone method. 19 Zr(H2O)2EDTA·2H2O was prepared as a white crystal according to the procedure 20 and a 1 × 10 -2 M (M = mol dm -3 ) stock solution was prepared using distilled water. Pyrocatechol Violet was purchased from Dojindo Laboratories, Japan and a 1 × 10 -3 M stock solution was prepared by dissolving an appropriate amount in distilled water. Working solutions, as required, of the above reagents were prepared by app...

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Section: Naked-eye Detection Of Fluoride and Advantagesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Naked-Eye Detection of Fluoride Using Zr(IV)-EDTA Complex and Pyrocatechol Violet

Balaji

Matsunaga

2005

ANAL. SCI.

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“…As such, traditional halide sensitive probes are not very sensitive to fluoride and are therefore not suited for detecting fluoride <50 mM [3]. Only a few fluorescent probes can be found in the literature which are sensitive to fluoride [31], all based on either the benzene or naphthalene backbone and therefore showing absorption in the deep UV (≈270 nm), which is not practical for many sensing applications [3,31,32]. Although water soluble sensor systems are deemed important, a few systems based on urea and thiourea based fluorophores were reported recently which show an optical response towards fluoride in organic media [33,34].…”

Section: Introductionmentioning

confidence: 99%

Wavelength–Ratiometric Probes for the Selective Detection of Fluoride Based on the 6-Aminoquinolinium Nucleus and Boronic Acid Moiety

Badugu

Lakowicz

Geddes

2004

Journal of Fluorescence

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Herein we report a set of new water-soluble fluorescent probes (N -boronobenzyl-6-aminoquinolinium bromides, BAQBAs) sensitive to aqueous fluoride. These probes shows spectral shifts and intensity changes in the presence of fluoride, in a wavelength ratiometric and colorimetric manner, enabling the detection of fluoride concentrations at visible wavelengths, in the concentration range ≈1-300 mM. Although the sensing mechanism is different for fluoride as compared to the other halides, we have tested the utility of these probes towards the other halides, and the results reveal that the BAQBAs are in fact potential candidates towards the sensing of the all the halides, but in different concentration ranges. As the probes are based on the boronic acid moiety, which is a well-known fluoride and sugar chelator group, we have investigated the response of sugars (such as glucose and fructose, which are present in biological fluids and foodstuffs) as interferences in fluoride detection using these probes. Interestingly, the BAQBAs show a suppressed sugar response potentially allowing for the predominant fluoride sensitivity. In addition to physiological sugars, we also have assessed the response of aqueous halides as potential interferents, or indeed analytes to be sensed, and show that the new boronic acid containing probes respond well to aqueous fluoride in the presence of a high background of other species, such as in a biological cocktail of 50 mM Glucose, 50 mM aqueous Chloride and 5 mM Fructose.

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“…Solvent effects play a crucial role in controlling the binding strength and selectivity for F  . On the other hand, there have been a few reports regarding F  detection using unique fluoride-boron [10][11][12][13][14][15][16][17][18][19] and fluoridesilica [20][21][22] interactions. To improve the sensitivity of the fluoride-induced-lactonization detection scheme, a semiconductor polymer that amplifies the response has been proposed [22].…”

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confidence: 99%

A near-infrared fluorescent probe for fluorine ions and its application in the imaging of HepG2 cells

Gong

Lü

et al. 2011

Chin. Sci. Bull.

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In this study, we have designed and synthesized a new near-infrared (NIR) fluorescent probe (BODIPY-Se) to detect fluorine ions (F  ) using a B-Se bond to connect the fluorescent dye BODIPY and benzotrifluoride. The probe exhibited a highly selective fluorescence response to F  with a detection limit of 7.4 × 10 8 mol/L. The excitation and emission spectra of the probe in the NIR region avoid background fluorescence interference present in biological systems. The fluorescent imaging of HepG2 cells demonstrated that the newly developed probe should be broadly applicable to detect F  in living cells.

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Selective fluorescence detection of fluoride using boronic acids

Cited by 229 publications

References 27 publications

Naked-Eye Detection of Fluoride Using Zr(IV)-EDTA Complex and Pyrocatechol Violet

Naked-Eye Detection of Fluoride Using Zr(IV)-EDTA Complex and Pyrocatechol Violet

Wavelength–Ratiometric Probes for the Selective Detection of Fluoride Based on the 6-Aminoquinolinium Nucleus and Boronic Acid Moiety

A near-infrared fluorescent probe for fluorine ions and its application in the imaging of HepG2 cells

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