Fluorescent Sensors for Transition Metals Based on Electron‐Transfer and Energy‐Transfer Mechanisms

Fabbrizzi, Luigi; Licchelli, Maurizio; Pallavicini, Piersandro; Perotti, Angelo; Taglietti, Angelo; Sacchi, Donatella

doi:10.1002/chem.19960020114

Cited by 266 publications

(144 citation statements)

References 20 publications

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“…More viscous media have the same effect. [56,57] Nevertheless, the pH response of these visibly excitable optode macro devices are clearly large enough to be useful. An additional positive feature is that there is no evidence of any aggregation of the dyes within the membrane under these conditions.…”

mentioning

confidence: 99%

Arenedicarboximide Building Blocks for Fluorescent Photoinduced Electron Transfer pH Sensors Applicable with Different Media and Communication Wavelengths

Daffy¹,

Silva²,

Gunaratne³

et al. 1998

Chem. Eur. J.

132

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N-(aminoalkyl)-4-chloronaphthalene-1,8-dicarboximides 1, N-(aminoalkyl)-4-acetamidonaphthalene-1,8-dicarboximides 3 and N,N'-bis(aminoalkyl)-perylene-3,4:9,10-tetracarboxydiimides 4 show good fluorescent off ± on switching in aqueous alcoholic solution with protons as required for fluorescent PET sensor design. The excitation wavelengths lie in the ultraviolet (l max 345 and 351 nm) for 1 and 3 and in the blue-green (l max 528, 492 and 461 nm) for 4; the emission wavelengths lie in the violet (l max 408 nm) for 1, in the blue (l max 474 nm) for 3 and in the yellow-orange (l max 543 and 583 nm) for 4. Compound 4 b shows substantial fluorescence enhancement with protons when immobilized in a poly(vinylchloride) matrix, provided that 2-nitrophenyloctyl ether plasticizer and potassium tetrakis(4-chlorophenyl)borate additive are present to prevent dye crystallization and to facilitate proton diffusion into the membrane, respectively.

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mentioning

confidence: 99%

Arenedicarboximide Building Blocks for Fluorescent Photoinduced Electron Transfer pH Sensors Applicable with Different Media and Communication Wavelengths

Daffy¹,

Silva²,

Gunaratne³

et al. 1998

Chem. Eur. J.

132

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“…Although fluorescence signaling offers the advantage of high sensitivity over absorption or reflectance signaling, only a few optical sensors based on fluorescence are reported for Cu 2+ determination. [10][11][12] These fluorescence sensors are commonly composed of two structural subunits: a fluorophore (for signal transduction) and an ionophore (for selective recongnition of metal ion). The two subunits are connected through a linking bridge.…”

Section: Introductionmentioning

confidence: 99%

An Optode Sensor for Cu2+ with High Selectivity Based on Porphyrin Derivative Appended with Bipyridine

et al. 2007

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Copper is an essential trace element in plants and animals. Following zinc and iron, it ranks the third in abundance in human bodies among the essential heavy metals. 1 Copper participates in many biological processes, such as haemoglobin synthesis (in Fe utilization and Hb regeneration), connective tissue development, normal functions of the central nervous system, and oxidative phosphorylation. [2][3][4] Owing to the growing awareness of the toxicity of copper at elevated concentrations, searching for effective analytical methods in general, and for optochemical sensors in particular, for the copper assay is of considerable interest.The recent years have seen a growing interest in the development of optical chemical sensors for Cu 2+ with different chemical transducers. [5][6][7][8][9] Thus optochemical sensors can offer advantages in terms of size, cost, not requiring a reference element, and transmitting without the influence of an electromagnetic field. Most of these optodes are based on absorption or reflectance measurements of immobilized colorimetric reagents in various matrices. Although fluorescence signaling offers the advantage of high sensitivity over absorption or reflectance signaling, only a few optical sensors based on fluorescence are reported for Cu 2+ determination. 10-12 These fluorescence sensors are commonly composed of two structural subunits: a fluorophore (for signal transduction) and an ionophore (for selective recongnition of metal ion). The two subunits are connected through a linking bridge. The fluorescence of the fluorophore would be affected when the ionophore recognizes some metal ions as a result of electron or energy transfer. 13,14 Searching for new fluorescence sensors which would respond toward Cu 2+ with sufficient high selectivity is still an active field as well as a challenge for the analytical chemistry research. [15][16][17][18][19] Porphyrins are a class of naturally occurring macrocyclic compounds, which play a very important role in the metabolism of living organisms. Moreover, porphyrins show good photophysical properties with large Stokes shifts and relatively long excitation (>400 nm) and emission (>600 nm) wavelengths that minimize the effects of the background fluorescence. This makes porphyrin derivatives potential fluorophores for preparation of new fluorescence molecular sensors. In the present study, a porphyrin derivative appended with bipyridine (H2TPPBPy) was chosen for preparation of a Cu 2+ -sensitive optical chemical sensor. H2TPPBPy has been used to investigate the rate of photoinduced charge separation. 20 Quenching of porphyrin fluorescence on irradiation is attributed to electron transfer from porphyrin to the acceptor (rhenium), which is linked with the porphyrin by bipyridine. It is interesting to explore the possibility of using a similar approach in designing the Cu 2+ -sensitive optical chemical sensor. Bipyridine coordination of Cu 2+ would quench the fluorescence of porphyrin. In this study, a sensor based on H2TPPBPy was first reported. T...

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“…[4] Compared with other copper(II) fluorosensors of this type described in recent years, [5] 1 combines a reversible response to nanomolar concentrations of Cu 2 in aqueous medium and low cross-sensitivity to certain transition metal ions and protons. When irradiated at 372 nm 1 displays an intense emission band at 415 nm.…”

mentioning

confidence: 99%

“…Metal-ion selectivity, binding kinetics, and proton cross-sensitivity are strongly dependent on the structure of the chelating group of the fluorescent sensor. [4] The membrane-based fluorosensor described by Arnold and coworkers is even more sensitive to Cu 2 . [6] Lipid 2 is functionalized with a fluorescent pyrene residue and a chelating iminodiacetate group.…”

mentioning

confidence: 99%

Fluorescent Chemosensors for Cu2+ Ions: Fast, Selective, and Highly Sensitive

Krämer

1998

Angewandte Chemie International Edition

554

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The design of chelating ligands for the selective complexation of metal ions has been an important goal of coordination and supramolecular chemistry for several decades. Chemical sensors for metal ions become accessible by combining a recognition event with an easily quantifiable signal event. The properties of an ªidealº sensor include high selectivity for one metal ion only, high sensitivity, fast and reversible (real-time) response, real-space response down to the micrometer level, and easy handling. Fluorescence signaling [1] offers the advantage of high sensitivity and can be directly used for sensors with fiber optic systems. A new generation of fluorescent reagents in which a chelating group and a fluorophore are discrete subunits of the same molecule [2] has the potential to fulfil the above-mentioned requirements. Recent attempts to apply these two-component systems to the detection of transition metal ions have been particularly successful in case of Cu 2 ions. This is not surprising, since among the more relevant transition metal ions, copper(ii) has a particularly high thermodynamic affinity for typical N,O-chelate ligands and fast metal-to-ligand binding kinetics. Copper is a significant metal pollutant due to its widespread use, but it is also an essential trace element in biological systems. Whereas copper toxicity for humans is rather low compared with other heavy metals, certain microorganisms are affected by submicromolar concentrations. Compared with classical fluorescence reagents for Cu 2 detection in which the donor atoms are part of the fluorophore p-system, [3] the spatial separation of chelating group and fluorophore offers considerable flexibility in design. This is a prerequisite for the straightforward optimization of sensor properties with a view to specific applications.

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Fluorescent Sensors for Transition Metals Based on Electron‐Transfer and Energy‐Transfer Mechanisms

Cited by 266 publications

References 20 publications

Arenedicarboximide Building Blocks for Fluorescent Photoinduced Electron Transfer pH Sensors Applicable with Different Media and Communication Wavelengths

Arenedicarboximide Building Blocks for Fluorescent Photoinduced Electron Transfer pH Sensors Applicable with Different Media and Communication Wavelengths

An Optode Sensor for Cu2+ with High Selectivity Based on Porphyrin Derivative Appended with Bipyridine

Fluorescent Chemosensors for Cu2+ Ions: Fast, Selective, and Highly Sensitive

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