A novel colorimetric sensor for anions recognition based on disubstituted phenylhydrazone

Hydrazone-based receptor containing electron-withdrawing chromogenic substituents 1,10-phenanthroline-2,9-di-carboxaldehydic-(2,4-dinitrophenyl)-hydrazone (1) has been synthesized. The interaction with different anions via hydrogen bonding was demonstrated by UV-Vis absorption spectroscopy to give a purple 1:1 complexes in DMSO, whose association constant decreases in line with the following order of the studied anions (AcO⁻ > F⁻ > H₂PO₄ ⁻ > OH⁻ >>Cl⁻∼Br⁻∼I⁻). As a naked-eyes colorimetric sensor for anions, the study has a latent application importance.      

A novel fluorescent and colorimetric anion sensor based on thiourea derivative in competitive media

A novel and simple fluorescent receptor bearing thiourea moiety as recognition site was described. The recognition behavior of the receptor toward different anions was investigated in DMSO/H(2)O (95:5 v/v) and dry DMSO through two various channels: the colorless-yellow color change and a remarkable enhancement of the fluorescence. And the enhancement of the fluorescence was attributed to an anion-induced increase of the rigidity of the host molecule.     

A naked-eye colorimetric sensor for chloroform

A phenoxazine based sensor molecule shows fast response (within 5 s) to halogenated solvents, especially chloroform via obvious color change under 365 nm UV light irradiation.     

A novel colorimetric and fluorometric anion sensor based on BODIPY-calix[4]pyrrole conjugate

A novel fluorescent anion sensor 1 based on boradiazaindacenes (BODIPY) derivative was synthesized and its absorption and fluorescence properties were investigated in various solvents. 1 exhibited a red shift of absorption spectrum and fluorescence quenching in varying degree in the presence of F^?, AcO^?, H₂PO₄ ^? and Cl^? due to multiple hydrogen bonding interactions between these anions and calix[4]pyrrole receptor. As an anion sensor in the visible region, 1 displayed the similar selectivity and sensitivity toward anions compared to the parent calix[4]pyrrole. However, 1 can be used as an effective dual responsive optical sensor for F^? via chromogenical and fluorogenical signals.     

Proton "off-on" behaviour of methylpiperazinyl derivative of naphthalimide: a pH sensor based on fluorescence enhancement

In a search for new type pH sensing fluorophores, the possibility of using the proton "off-on" switch behaviour of naphthalimide derivatives for optical pH sensor preparation has been explored. A new compound, N-allyl-4-(4[prime or minute]-methyl-piperazinyl)-1,8-naphthalimide (AMPN), was synthesized. The enhancement of fluorescence of AMPN with the increase of hydrogen ion concentration is based on arresting photo-induced electron transfer to the naphthalimide fluorophore from aliphatic amine group after its protonation. The Stokes Shift of the proposed type of pH sensing fluorophore is significantly larger than that of the fluorescein counterparts. To avoid the leakage of the fluorophore, AMPN was photo-copolymerized with 2-hydroxyethyl methacrylate and acrylamide on the glass surface. The fluorescence intensity of membrane contacted with a pH 3.50 buffer is 4.7 times of that for pH 12.00 buffer solutions. The proposed pH sensor is not susceptible to ionic strength and shows good selectivity, repeatability and short response time. The membrane shows a good stability with a lifetime over two months. The sensor can be used for the determination of pH in the range of pH 4.5-9.0, without interference of most commonly co-existing inorganic ions and some organic species. The sensor has been applied to the analysis of urine samples.     

A novel anthracene-based fluorescent colorimetric sensor for the simple naked-eye diagnosis of methylmalonic aciduria

A novel molecular sensor using anthracene bearing two amidopyridines emits blue fluorescence in the presence of succinic acid and green fluorescence in the presence of malonic acid, and its fluorescence intensity increased upon binding. Using this molecular sensor, we succeeded in detecting the difference of one carbon atom between succinic acid and malonic acid with the naked-eye. Furthermore, when methylmalonic acid was dissolved in urine to provide a model system for methylmalonic aciduria, the fluorescence changed from blue to green, and methylmalonic acid was successfully detected with the naked-eye.     

"Janus" supermolecular liquid crystals--giant molecules with hemispherical architectures

Liquid crystals represent a unique class of self-organising systems, which although found in many day-to-day practical material applications, such as displays, are also intimately entwined with living processes. They have the potential, just like living systems, to provide us with a unique vehicle for the development of self-ordering nano- and mesoscopic-engineered materials with specific functional properties. In this article we describe a new concept for the design of self-assembling functional liquid crystals as segmented or "Janus" liquid-crystalline supermolecular materials in the form of structures that contain two different types of mesogenic units, which favour different types of mesophase structure, grafted onto the same star-shaped scaffold to create supermolecules that contain different hemispheres. The materials exhibit chiral nematic and chiral smectic C phases.     

A highly selective colorimetric aqueous sensor for mercury

A new colorimetric mercury sensor is reported based on binding to terpyridine derivatives. It is able to selectively detect Hg II ions over a number of environmentally relevant ions including Ca II, Pb II, Zn II, Cd II, Ni II, Cu II, and others. The response time upon exposure to Hg II is instantaneous. By the "naked eye," the detection limit of Hg II is 2 ppm (25 microM) in solution. With a spectrometer, this detection limit is increased down to 2 ppb (25 nM), which is the current EPA standard for drinking water. The significant problem of mercury poisoning requires new methods of detection that are sensitive and selective. Here we report a new simple system that takes advantage of the unique optical properties generated by terpyiridine-Hg complexes.     

A colorimetric sensor array for organics in water

Molecular recognition of organic compounds in aqueous solutions is inherently challenging due to the potential interference from the very high concentration of water. Here we present a simple colorimetric sensor array that probes a wide range of chemical properties. By printing hydrophobic dyes on a hydrophobic membrane, sensor arrays are easily prepared that provide substantial chemical selectivity for the identification and quantification of various organics (both single compounds and complex mixtures) dissolved in water. It is possible to differentiate easily even among closely related organic compounds. Upon immersion in aqueous solutions, digital imaging of the dye array before and after exposure to an analyte provide a color change profile that is a fingerprint for the organic components of the solution. Facile identification of a wide variety of aqueous organic solutions is possible over a concentration range of 0.1 M to 1 muM. Complex mixtures present no inherent difficulty; for example, a series of commercial soft drinks were easily distinguished using the colorimetric sensor array approach.     

An off-on fluorescent sensor with high selectivity and sensitivity for Fe(III)

A new fluorescent derivative (1) containing coumarin exhibits Fe(III)-selective strong yellow-green fluorescence in ethanol. This compound could be used as an “off-on” chemosensor and allow the detection of Fe³⁺ by monitoring changes in absorption and fluorescence spectra. Upon addition of Fe³⁺, an overall emission change of 125-fold was observed. High selectivity and sensitivity were observed over other metal ions, mainly due to the spirolactam ring-opening power of Fe³⁺. The detection limit was as low as 5.6?ppb. Photo-induced electron transfer, coupled with intramolecular charge transfer are proposed to account for the observed spectral response.     

A simple naphthalene-based colorimetric sensor selective for acetate

A new naphthalene based receptor (L) has been designed and synthesized which shows a remarkable color change from colorless to pink on selective binding with acetate. The anion recognition property of the receptor via hydrogen bonding interactions is monitored by UV-vis, fluorescence, and ¹H NMR titrations. It is observed that in each case, the receptor shows a specific selectivity toward the acetate ion over other interfering anions. Thus, a significant bathochromic shift in UV-vis spectrum with a sharp pink color in ‘naked-eye’ makes the receptor suitable for the detection of the acetate ion.     

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 colorimetric sensor array for detection and identification of sugars

Molecular recognition of sugars and a practical method to detect and discriminate among a large number of such similar analytes remain substantial scientific challenges. We report here a low-cost, simple colorimetric sensor array capable of identification and quantification of sugars and related compounds. Fifteen different monosaccharides, disaccharides, and artificial sweeteners were differentiated without error in 80 trials. Limits of detection at pH 7.4 for glucose were <1 mM, which is below physiologically important levels.     

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.     

A novel colorimetric and ratiometric NIR fluorescent sensor for glutathione based on dicyanomethylene-4H-pyran in living cells

Glutathione (GSH) plays a critical role in maintaining oxidation-reduction homeostasis in biological systems. Considering the detection of GSH by fluorescence sensors is limited by either the short wavelength emission or the poor photostability, a highly stable colorimetric and ratiometric NIR fluorescent sensor (DCM-S) for GSH detection has been constructed on the basis of dicyanomethylene-4H-pyran (DCM) chromophore. The specific disulfide bond is incorporated via a carbamate linker as the GSH responsive group, which simultaneously blue-shifts and quenches the fluorescence. Upon addition of GSH, DCM-S exhibits outstanding colorimetric (from yellow to red) and ratiometric fluorescent response with the 6-fold enhancement of NIR fluorescence at 665 nm in quantum yield. More importantly, the GSH-treated DCM-S (DCM-NH₂ actually) possesses 20-fold longer fluorescence half-life period as well as much better photostability than the FDA-approved ICG. Finally, the ratiometric detection of GSH is also successfully operated in the living cell imaging, exhibiting NIR fluorescence and large Stokes shift (215 nm) with nearly no background fluorescence interference. As a consequence, DCM-S can be utilized as colorimetric and ratiometric NIR fluorescent sensor for GSH, with a great potential in the development of GSH-induced drug delivery system.     

Facile synthesis of rhodamine-based highly sensitive and fast responsive colorimetric and off-on fluorescent reversible chemosensors for Hg2+: preparation of a fluorescent thin film sensor

Fluorescence-active chemosensors (L1-L4), comprising a rhodamine scaffold and a pseudo azacrown cation-binding subunit, have been proposed and characterized as a fluorescent chemosensor for Hg(2+). An on-off type fluorescent enhancement was observed by the formation of the ring-opened amide form of the rhodamine moiety, which was induced by the interactions between Hg(2+) and the chemosensor. Upon the addition of Hg(2+), an overall emission change of 350-fold was observed, and the selectivity was calculated to be 300 times higher than Cu(2+) for receptors L2-L4. A polymeric thin film can be obtained by doping poly(methyl methacrylate) or PMMA with chemosensor L2. Such a thin film sensor can be used to detect Hg(2+) with high sensitivity and can be recovered using diluted NaOH.     

Hexaphyrin(1.0.1.0.0.0). A new colorimetric actinide sensor

Hexaphyrin(1.0.1.0.0.0) (isoamethyrin) undergoes a significant color change in the presence of UO₂²⁺, PuO₂²⁺, and NpO₂²⁺. The complexation of the first of these dioxo actinide cations was studied in semi-quantitative fashion in 1:1 MeOH-CH₂Cl₂. Under these conditions, the detection limit for UO₂²⁺ was found to be ca. 5.8 ppm by naked eye monitoring and <28 ppb by UV-vis spectroscopy. Isoamethyrin does not undergo a color change in the presence of most transition metals or when exposed to Gd(III). Isoamethyrin thus constitutes an attractive alternative to 2,2′(1,8-dihydroxy-3,6-disulfonaphthylene-2,7-bisazo)-bisbenzenarsonic acid (AzIII) and 2-(5-bromo-2-pyridylazo)-5-(diethylamino)phenol (BrPADAP), systems currently used as actinide cation sensors.     

A colorimetric tetrathiafulvalene-calix[4]pyrrole anion sensor

The interaction and colorimetric sensing properties of a tetrathiafulvalene substituted calix[4]pyrrole sensor with anions were investigated using ¹H NMR and absorption spectroscopic techniques. Visual color changes were observed upon addition of different anions (Cl⁻, Br⁻, CN⁻, and AcO⁻) to a solution of the sensor.     

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.