Ratiometric Fluorescent Chemodosimeter Research Articles

Flavone-Based ESIPT Ratiometric Chemodosimeter for Detection of Cysteine in Living Cells

We have designed and synthesized a novel ratiometric fluorescent chemodosimeter MHF-based ESIPT process for specific detection of cysteine among the biological thiols. The probe MHF shows very weak blue fluorescence under UV excitation. Upon addition of cysteine (Cys), the reaction of Cys with MHF induces acrylate hydrolysis, thereby enabling the ESIPT process to shift the weak blue emission to a strong green emission with about 20-fold enhancement. We utilized 1H NMR spectra to elucidate the fluorescence sensing mechanism. Moreover, the cellular imaging experiment indicated the MHF possessed excellent selectivity, low cytotoxicity, and desirable cell permeability for biological applications.

Surfactant-sensitized ratiometric fluorescent chemodosimeter for the highly selective detection of mercury(ii) ions based on vinyl ether oxymercuration

The ratiometric fluorescence chemodosimeter N-butyl-4-(prop-1-en-1-yloxy)-1,8-naphthalic anhydride (NT-VE) was designed for Hg2+ recognition by oxymercuration at ambient temperature with high selectivity and no interference from other metal cations such as Cu2+, Ag+, Au3+, Fe3+, etc. The NT-VE could be incorporated into sodium dodecyl-benzenesulfonate (SDBS) micelles, which was confirmed by the clear emission enhancement observed in 0.1 mM SDBS. The hydrophobic core of the SDBS enhanced the solubility of NT-VE, enabling the detection of Hg2+ in aqueous solution, and the negatively charged micelle surface increased the local concentration of Hg2+ for amplified sensitivity. This work demonstrated the excellent performance of the NT-VE chemodosimeter for ratiometric detection of Hg2+ in aqueous solution. The NT-VE/SDBS system could detect Hg2+ over a linear range of 0.05–10 μM and a detection limit of 9 ppb (45 nM) in water.

A sensitive colorimetric and ratiometric fluorescent chemodosimeter for Hg2+and its application for bioimaging

A colorimetric and ratiometric fluorescent chemodosimeter for Hg2+ has been developed based on mercury ion-promoted hydrolysis of a naphthalimide-derived aryl vinyl ether. The chemodosimeter displays a highly sensitive and selective response with significant changes in both color (from colorless to jade-yellow) and fluorescence (from blue to green) in PBS buffer solution (containing 1% CH3CN, pH = 7.4). The chemodosimeter exhibits a ratiometric fluorescent response towards Hg2+ with a very low detection limit (3.6 nM), which can be used to detect Hg2+ ions in drinking water. Furthermore, the chemodosimeter has been successfully applied to the imaging of Hg2+ ions in living cells with an emission change from blue to green.

A facile ratiometric fluorescent chemodosimeter for hydrazine based on Ing–Manske hydrazinolysis and its applications in living cells

A facile and sensitive fluorescent probe for hydrazine was successfully constructed, displaying excellent colorimetric and ratiometric responses towards hydrazine via Ing–Manske hydrazinolysis conditions in semi-aqueous buffer solution. Semi-empirical calculations as well as spectroscopic results revealed the signalling mechanism of the current probe under hydrazinolysis conditions, in which hydrazine exclusively deprotected the phthalimide group by an intermediate of phthalhydrazide. Extensive screening of pH effects on the probe with the aid of proton nuclear magnetic resonance and mass spectrometry supported the distinctive and diverse ratiometric responses under hydrazinolysis and basic hydrolysis conditions. Time resolved photoluminescence measurements of the probe further confirmed its discernible ratiometric responses probed at respective wavelengths. A distinctive ratiometric response under basic hydrolysis conditions and a successful utilization of probe towards hydrazine detection in living cells are demonstrated.

A highly selective colorimetric and ratiometric fluorescent chemodosimeter for detection of fluoride ions based on 1,8-naphthalimide derivatives

A high selective colorimetric and ratiometric fluorescent probe based on 4-hydroxy-1, 8-naphthalimide was designed and synthesized to detect fluoride ions (F−). The sensing behavior of this probe was studied by UV–visible and fluorescence spectroscopy. The probe displays an 110nm red-shift of fluorescence emission and the color changes from colorless to yellow by virtue of the strong affinity of F− toward silicon which can act as a new visual sensor for F−.

BODIPY-based sulfoxide: Synthesis, photophysical characterization and response to benzenethiols

Abstract Two BODIPY dyes bearing a sulfur containing function at the 3-position are reported. The 3-benzylthio compound shows spectroscopic features of the classical BODIPY platform, showing minor solvent dependent spectral shift, a relative small Stokes shift and a high fluorescence quantum yield. Oxidation of the sulfur atom to the sulfoxide leads to a large hypsochromic shift in absorption and emission. We also demonstrated that the sulfoxide derivative can be used as a ratiometric fluorescent chemodosimeter for highly toxic benzenethiols in aqueous media. In this dosimeter the sulfoxide is chemospecifically reduced by benzenethiols to obtain the original oxidation state of the sulfur atom, accompanied with a drastic ratiometric fluorescence response. Furthermore, the probe features excellent selectivity over other competing analytes, moderate signal response times and a good linearity range for quantification. All these features render the sensor suitable for detection of benzenethiols in environmental settings.

Ratiometric Fluorescence Detection of Mercury Ions in Water by Conjugated Polymer Nanoparticles

We present dye-doped polymer nanoparticles that are able to detect mercury in aqueous solution at parts per billion levels via fluorescence resonance energy transfer (FRET). The nanoparticles are prepared by reprecipitation of highly fluorescent conjugated polymers in water and are stable in aqueous suspension. They are doped with rhodamine spirolactam dyes that are nonfluorescent until they encounter mercury ions, which promote an irreversible reaction that converts the dyes to fluorescent rhodamines. The rhodamine dyes act as FRET acceptors for the fluorescent nanoparticles, and the ratio of nanoparticle-to-rhodamine fluorescence intensities functions as a ratiometric fluorescence chemodosimeter for mercury. The light harvesting capability of the conjugated polymer nanoparticles enhances the fluorescence intensity of the rhodamine dyes by a factor of 10, enabling sensitive detection of mercury ions in water at levels as low as 0.7 parts per billion.

A ratiometric fluorescent chemodosimeter for Cu(II) in water with high selectivity and sensitivity

Coumarin derivative 1 was synthesized as an efficient ratiometric chemodosimeter for the detection of Cu(II) in 99% water/DMSO ( v/ v) at pH 7.0. Mechanism studies suggested that 1 formed a complex with Cu(II) at 2:1 ratio accompanied by quenching of green fluorescence at 524 nm; when the solution was heated to 50 °C for 30 min, Cu(II)-promoted hydrolysis of coumarin lactone moiety of 1 occurred with bright blue fluorescence at 451 nm emerged. With fluorescence intensity ratio detection at 451 nm and 524 nm, 1 features an excellent sensitivity with the detection limit of 15 nmol L −1 toward Cu(II) and a good selectivity over other metal ions.

A 4-hydroxynaphthalimide-derived ratiometric fluorescent chemodosimeter for imaging palladium in living cells

A highly selective ratiometric fluorescent chemodosimeter derived from 4-hydroxynaphthalimide was designed and synthesized to image palladium species in living cells by virtue of a palladium-catalyzed depropargylation reaction, and it could monitor three typical palladium species (0, + 2 and + 4) without additional reagents.

A highly selective colorimetric and ratiometric fluorescent chemodosimeter for imaging fluoride ions in living cells

A simple but highly selective colorimetric and ratiometric fluorescent chemodosimeter was designed and synthesized to detect fluoride ions (F(-)) in aqueous solution and living cells by virtue of the strong affinity of F(-) toward silicon.

A Ratiometric Fluorescent Chemodosimeter with Selective Recognition for Sulfite in Aqueous Solution

A fluorescent chemodosimeter containing a guanidiniocarbonylpyrrole and a 9-(aminomethyl)anthracene moiety has been synthesized. The sensor exhibits ratiometric fluorescence changes for SO(3)(2-) over other anions in 90% water/DMSO. The interesting ratiometric fluorescent changes for SO(3)(2-) are attributed to the fluorescence resonance energy transfer (FRET) and the SO(3)(2-) complex induced photochemical reaction.

Ratiometric and selective fluorescent chemodosimeter for Cu(II) by Cu(II)‐induced oxidation

A new rhodamine derivative, rhodamine B 4-N,N-dimethylaminobenzaldehyde hydrazone (1), was designed for ratiometric sensing of Cu(II) selectively. A red-shift from 515 to 585 nm was observed in the fluorescence spectrum when Cu(II) was added to 1 in acetonitrile. Other metal ions of interest showed no ratiometric response. The interaction between Cu(II) and 1 was found to be the Cu(II)-induced oxidation of 1.