A novel fluoride ion colorimetric chemosensor

A novel phosphonium derivative of naphthalene was synthesized by the reaction of 1,8-dibromomethylnaphthalene with triphenylphosphine, which only showed a distinct color change when treated with fluoride ions.     

A coumarin-based fluorescent and colorimetric chemosensor for rapid detection of fluoride ion

A novel coumarin-based compound 1 featuring thiosemicarbazone as binding unit, was reported as a colorimetric and fluorescent probe for the detection of fluoride anion. The addition of F^? to a solution of probe 1 in tetrahydrofuran resulted in evident naked-eye color change from green-yellow to orange-red under daylight and obvious fluorescence quenching within 3 s. And the detection limit toward F^? was calculated to be as low as 2.16 × 10^?7 mol/L. ¹H NMR titrations proved that the interaction between 1 and fluoride ion: hydrogen bond at low fluoride ion concentration, deprotonation at high fluoride ion concentration. Besides, it exhibited highly sensitivity and selectivity for F^? over other examined ions (Cl^?, Br^?, I^?, AcO^?, NO₃^?, HSO₄^?, H₂PO₄^?) in tetrahydrofuran solution.     

Cyanide ion colorimetric chemosensor based on protonated merocyanine in EtOH

This Letter aimed to develop an efficient method for the determination of cyanide ion (CN⁻). A novel colorimetric chemosensor 4-[(1E)-2-(4-hydroxyphenyl)ethenyl]-1-allylpyridinium bromide (HPEAPB) was synthesized. HPEAPB displayed good selectivity toward CN⁻ over other competing anions in ethanol. A color change from yellow to red was immediately observed upon the addition of CN⁻ and the limit of detection (LOD) was 3.4 × 10⁻⁶ mol L⁻¹. The sensing mechanism was discussed by UV–vis, ¹H NMR titration, and a comparison study. Colorimetric test paper for CN⁻ was prepared by attaching HPEAPB to a chromatography paper, which could be used to detect CN⁻ in environmental samples as simply as a pH-indicator paper for pH value. The LOD of the test paper for CN⁻ was 2.0 × 10⁻⁴ mol L⁻¹. This detection method for CN⁻ has potential applications in cyanide ion containing fields by combination of rapid and real-time advantages.     

A colorimetric chemosensor for both fluoride and transition metal ions based on dipyrrolyl derivative

The synthesis, characterization and ion binding studies of 2,3-di(1H-2-pyrrolyl)pyrido[2,3-b]pyrazine (1) have been described. 1, which has been targeted with a view to sensing both F- and transition metal ions, exhibits binding-induced color changes from yellowish green to red/brown observable by the naked eye. The binding site for the metal ion in the system has been unambiguously established by single-crystal X-ray diffraction study of a Ni(II) complex of 1. While the estimated value of the binding constant of 1 with F- is 4.9 x 10(3) M(-1), the binding constants for the cations are found to be two orders higher in magnitude in acetonitrile. Even though 1 possesses two separate binding sites for F- and metal ions, it is shown that the presence of the cation influences the binding of the anion and vice versa. The binding constant values of an ion in the presence of oppositely charged species are measured to be significantly lower.     

A novel fluoride selective optical chemosensor based on internal charge transfer signaling

A new internal charge transfer probe, NAPH-1, synthesized by incorporating photoemitive naphthalimide core with an acidic imidazolium ring, offers highly selective colorimetric and ratiometric ‘off-on’ signaling for targeting F⁻, while Cl⁻, Br⁻, I⁻, , SCN⁻, AcO⁻, and do not appreciably perturb the photophysical properties of the probe even at relatively higher concentrations than the F⁻. Deprotonation of the imidazolium ring, supported by the ¹H NMR and theoritical studies, seems to cause the spectral modulations.     

A ditopic colorimetric sensor for fluoride ion based on thiourea mercury complex

A novel ditopic chromogenic receptor, N-5-(8-hydroxy)quinoline-N'-4'-nitro-phenyl thiourea (1), was synthesized. The metal complex 1-Hg(2+) showed sensitive and highly selective responses to F(-) over other anions such as CH(3)CO(2)(-), H(2)PO(4)(-), HSO(4)(-) and Cl(-). 1-Hg(2+)-F(-) complex formed, which promoted the intramolecular charge transfer and led to a dramatic spectral change. The color of 1-Hg(2+) solution changed from colorless to red upon addition of F(-). Thus, a colorimetric assay of F(-) was developed in acetonitrile by naked-eye detection. F(-) behaved linearly in the 8.0 x 10(-6) to 2.0 x 10(-5) mol L(-1) concentration range with LOD as 1.4 x 10(-6) mol L(-1).     

A new colorimetric and fluorescent chemosensor based on thiacalix[4]arene for fluoride ions

A new thiacalix[4]arene based fluorescent chemosensor thiacalix[4]arene-N-(quinolin-8-yl)acetamide (TCAN8QA) has been synthesized. TCAN8QA has been found to exhibit highly selective behavior for F⁻ ions among all other anions, that is, Cl⁻, Br⁻, I⁻, PO₄⁻³, OH⁻, H₂PO₄⁻, and CH₃COO⁻ in the absorption spectra as well as in the emission spectra. Red shift and quenching in emission spectra constituting the signature for fluoride detection are due to photoinduced charge transfer (PCT) which can be attributed to deprotonation of acidic NH proton in the presence of fluoride ions.     

A novel colorimetric and fluorescent anion chemosensor based on the flavone quasi-crown ether-metal complex

The metal-ligand complex 1 ([Mg (L)] (2+)) (or 2 ([Ca (L)]( 2+))) was demonstrated to selectively bind HSO(4)(-) (or H(2)PO(4)(-)) over other anions by using UV-vis absorption and fluorescence spectroscopy. The studied complex exhibits the remarkable color change and fluorescence quenching upon introducing HSO(4)(-) (or H(2)PO(4)(-)) anion in acetonitrile. Both the mechanism and structure of the secondary complex of complex 1 with anion were proposed on the basis of theoretical computation.     

Visible colorimetric fluoride ion sensors

[structure: see text] Five new urea derivative naphthalene compounds were synthesized by a reaction of 1,8-diaminonaphthalene and the corresponding isocyanates and showed a distinct color change only when treated with fluoride ions.     

A naked-eye,selective and sensitive chemosensor for fluoride ion

Effect of the addition of six different anions on the absorption and fluorescence spectra of acridine yellow G (AYG) was examined. Only the F⁻ anion could induce a visible color change observable with naked eye and a strong fluorescence quenching with K _SV of 8.3 × 10⁴ mol⁻¹ L in CH₃CN solutions. Calculated results of the interaction between the F⁻ anion and acridine yellow G using the B3LYP/6-31G(d) program showed that the intermolecular charge transfer through the formation of an H-bond between AYG and F⁻ is an essential sensor mechanism.     

Aminobenzohydrazide based colorimetric and ‘turn-on’ fluorescence chemosensor for selective recognition of fluoride

Chemosensors based on aminobenzohydrazide Schiff bases bearing pyrene/anthracene as fluorophores have been designed and synthesized for F⁻ ion recognition. The addition of fluoride ions to the receptors causes a dramatically observable colour change from pale yellow to brown/red. ¹H NMR studies confirm that the F⁻ ion facilitates its recognition by forming hydrogen bond with hydrogens of amide and amine groups. Moreover these sensors have also been successfully applied to detection of fluoride ion in commercial tooth paste solution.     

A selective colorimetric chemosensor for thiols based on intramolecular charge transfer mechanism

Compound 1 as an electron donor-acceptor compound with N,N-dimethylaniline and quinone units was designed for a highly selective colorimetric determination of thiol-containing amino acids and peptides, by making use of the unique reactivity of thiol towards quinone. Compound 1 shows a strong intramolecular charge transfer (ICT) band around 582 nm; but, it decreased after addition of either cysteine (Cys) or glutathione (GSH). Moreover, the ICT band intensity at 582 nm decreased linearly with the increasing concentrations of Cys or GSH. The interference from other amino acids can be neglected. Therefore, compound 1 can be employed as a selective colorimetric visual chemosensor for thiol-containing amino acids and peptides.     

A fluoride selective dipyrromethane-TCNQ colorimetric sensor based on charge-transfer

A colorimetric sensor based on dipyrromethane(donor)-7,7′,8,8′-tetracyanoquinodimethane (acceptor) charge-transfer compound depicts excellent selectivity for naked-eye as well as spectrophotometric determination of F⁻ even in co-existence with other halide ions (Cl⁻, Br⁻ and I⁻). The sensing mechanism is ascribed to the interrupted charge-transfer between donor-acceptor in the presence of F⁻. The sensing on solid support mimics the solution sensing process supported by the reflectance values. Thus this compound has potential for practical applications.     

A highly sensitive colorimetric and ratiometric sensor for fluoride ion

A new benzoimidazole-naphthalimide derivative 4 was synthesized and its photophysical properties were studied. This compound showed highly selectively and sensitive colorimetric and ratiometric sensing ability for fluoride anion.     

Novel fluorescent chemosensor for Ag^ ＋ based on coumarin fluorophore

A novel chemosensor 1 （CS1） bearing one coumarin and two carbodithioate groups was synthesized and its fluorescent sensing behavior toward metal ions was investigated. Ag^＋ addition to a CH3COCH3/H2O （3：7, v：v） solution of CS1 gave a significantly quenched fluorescence. Other ions including Pb^2＋, Zn^2＋, Cu^2＋, Ca^2＋, Cd^2＋, Co^2＋, Mg^2＋, Mn^2＋, Hg^2＋, Ag^＋, Ni^2＋ induced no or much smaller spectral changes. This constitutes an ON-OFF Ag^＋-selective fluorescent chemosensor.     

A fluorescent chemosensor for fluoride anions based on a hemicyanine dye

A hemicyanine dye with imidazole as the acceptor was designed and prepared as a chemosensor for fluoride anions. The experimental results demonstrated that it is a fluorometric probe for fluoride anion with good sensitivity and high selectivity. This probe showed obvious changes in UV–Vis absorption and fluorescence spectra in the presence of fluoride anions, which are attributed to the deprotonation of N–H on the imidazole moiety with fluoride anions.     

A new fluorescent-colorimetric chemosensor for fluoride anion based on benzimidazolium salt

Two new benzimidazolium salts with the same cationic moiety and different anions 3-(2′-((8″-hydroxy-9″,10″-dioxo-9″,10″-dihydroanthracen-1″-yl)oxy)ethyl)-1-(pyridin-2?-ylmethyl)-1H-benzo[d]imidazol-3-ium bromide and 3-(2′-((8″-hydroxy-9″,10″-dioxo-9″,10″-dihydroanthracen-1″-yl)oxy)ethyl)-1-(pyridin-2?-ylmethyl)-1H-benzo[d]imidazol-3-ium hexafluorophosphate were prepared and characterized. The single crystal structure of 3-(2′-((8″-hydroxy-9″,10″-dioxo-9″,10″-dihydroanthracen-1″-yl)oxy)ethyl)-1-(pyridin-2?-ylmethyl)-1H-benzo[d]imidazol-3-ium bromide was determined by X-ray single crystal diffraction. Particularly, anion recognition using 3-(2′-((8″-hydroxy-9″,10″-dioxo-9″,10″-dihydroanthracen-1″-yl)oxy)ethyl)-1-(pyridin-2?-ylmethyl)-1H-benzo[d]imidazol-3-ium hexafluorophosphate as a chemosensor was carried out via fluorescence and ultraviolet spectroscopy, ¹H NMR titrations, HRMS and IR spectra. The response of this chemosensor to fluoride anion can be observed through both remarkable fluorescence quenching and color change under visible light (from orange to purple). The results indicated that this chemosensor can distinguish fluoride anion from other anions via the instrument and naked eyes, and this is greatly convenient in practical operation.