Dipyrrolylquinoxalines:  Efficient Sensors for Fluoride Anion in Organic Solution

Black, Christopher B.; Andrioletti, Bruno; Try, Andrew C.; Ruiperez, Cristina; Sessler, Jonathan L.

doi:10.1021/ja992579a

Cited by 398 publications

(198 citation statements)

References 13 publications

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“…3) suggested that Zr-EDTA and PV form both 1:1 and 2:1 complexes, as given in Eqs. (1) and (2). In the later case, PV acts as a ligand for a binuclear metal complex through two sets of catechol-like parts (Schemes 1 and 2).…”

Section: Optimization Of Conditionsmentioning

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: Optimization Of Conditionsmentioning

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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“…The binding units are often composed of amide, 17 urea / thiourea and pyrrole owing to their binding ability performing as hydrogen donors. [18][19][20][21] Anions are ubiquitous throughout biological systems. Some anions such as fluoride, chloride, bromide, acetate, dihyphosphate, and etc play important roles in a range of biological process and are implicated in many disease states.…”

Section: Introductionmentioning

confidence: 99%

Theoretical and experimental study of organic nano-material for acetate anion based on 1, 10-phenanthroline

Shang

Fan²,

Fu³

et al. 2015

ACSi

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New phenanthroline derivatives containing phenol groups have been synthesized and optimized. The nano-material involved bromine substituent was also developed which in the ortho-position of benzene ring. Their binding properties were evaluated for various biological anions (F -, Cl -, Br -, I -, AcO -and H 2 PO 4 -) by theoretical investigation, UV-vis, fluorescence, 1 H NMR titration experiments. These compounds all showed strong binding ability for AcO -without the interference of other anions tested. The anion binding ability could be regularized by electron push-pull properties of the ortho-or para-substituent on benzene. Theoretical investigation analysis revealed the effect of intramolecular hydrogen bond existed between -OH and other atoms in the structure of these compounds.

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“…It is well known that the quinoxaline derivatives are used as dyes to detect metals and anions. 1,2 They are also used as agrochemicals, 3 anti-virals, 4 antimicrobials, 5 and for the treatment of tuberculosis, 6 and human cancer cell lines, 7 and herbicides. 8 We have continued our investigations and prepared new quinoxaline derivatives in the hope that they may possess various pharmacological activities.…”

Section: Introductionmentioning

confidence: 99%

A convenient synthesis of new pyrazolylquinoxalines from 1,5-benzodiazepine-2-thione

Doumbia¹,

Bouhfid²,

Ahabchane³

et al. 2008

Arkivoc

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Dipyrrolylquinoxalines: Efficient Sensors for Fluoride Anion in Organic Solution

Cited by 398 publications

References 13 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

Theoretical and experimental study of organic nano-material for acetate anion based on 1, 10-phenanthroline

A convenient synthesis of new pyrazolylquinoxalines from 1,5-benzodiazepine-2-thione

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