Fluorescent photoionic devices with two receptors and two switching mechanisms: applications to pH sensors and implications for metal ion detection

Callan, John F.; Silva, A. Prasanna de; Ferguson, Joanne; Huxley, Allen J. M.; O'brien, Aoife Mary

doi:10.1016/j.tet.2004.08.057

Cited by 73 publications

(37 citation statements)

References 58 publications

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“…A fluorescence decrease to the basal level (close to zero) caused by deprotonation was subsequently observed when NaOH solution was added to the mixture (Figure 4 B). The weak fluorescence can be even more sensitive to 2,4-DCAA after the first protonation/deprotonation cycle, [17] and an eightfold fluorescence enhancement was observed for the system when 2,4-DCAA solution was added to the mixture again (Figure 4 C). Although the response decreased slightly with repetition, no significant loss of 2,4-DCAA sensitivity was exhibited for at least five repeated cycles.…”

Section: Resultsmentioning

confidence: 99%

A Reversible Dual‐Response Fluorescence Switch for the Detection of Multiple Analytes

Geng

Liu

et al. 2010

Chemistry A European J

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This paper reports a reversible dual fluorescence switch for the detection of a proton target and 2,4,6-trinitrotoluene (TNT) with opposite-response results, based on fluorophore derivatization of silica nanoparticles. Fluorescent silica nanoparticles were synthesized through modification of the surface with a nitrobenzoxadiazole (NBD) fluorophore and an organic amine to form a hybrid monolayer of fluorophores and amino ligands; the resultant nanoparticles showed different fluorescence responses to the proton target and TNT. Protonation of the amino ligands leads to fluorescence enhancement due to inhibition of photoinduced electron transfer (PET) between the amine and fluorophore. By contrast, addition of TNT results in fluorescence quenching because a fluorescence resonance energy transfer (FRET) happens between the NBD fluorophore and the formed TNT-amine complex. The fluorescence signal is reversible through washing with the proper solvents and the nanoparticles can be reused after centrifugal separation. Furthermore, these nanoparticles were assembled into chips on an etched silicon wafer for the detection of TNT and the proton target. The assembled chip can be used as a convenient indicator of herbicide (2,4-dichlorophenoxyacetic acid) and TNT residues with the use of only 10 microL of sample. The simple NBD-grafted silica nanoparticles reported here show a reversible signal and good assembly flexibility; thus, they can be applied in multianalyte detection.

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Section: Resultsmentioning

confidence: 99%

A Reversible Dual‐Response Fluorescence Switch for the Detection of Multiple Analytes

Geng

Liu

et al. 2010

Chemistry A European J

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“…1b). [16][17][18][19] Colorless crystals of L suitable for X-ray crystallography were grown by vapor diffusion of diethyl ether into a dichloromethane solution of this ligand at room temperature. The molecular structure of L is shown in Fig.…”

Section: Resultsmentioning

confidence: 99%

“…The 7-nitrobenzo-2-oxa-1,3-diazolyl (NBD) unit is a chromo/fluorophore and seemed ideal probe for incorporation in new type of dual-signaling receptors. [16][17][18][19] As an extension of our previously results for the Hg 2+ sensing host system with mono-channel (color) probe, 12 we have worked on the functional macrocycle in terms of the construction of dual-channel (color/fluorescence) probe sensing system. We herein report the synthesis of NBD-attached NO 2 S 2 macrocycle L (Scheme 1) and its photophysical behaviors as a mercury(II) sensor.…”

Section: Introductionmentioning

confidence: 92%

A Chromo- and Fluoroionophoric Thiaoxaaza-Macrocycle Functionalized with Nitrobenzofurazan Exhibiting Mercury(II) Selectivity

Lee¹,

Lee²,

Choi³

2010

Bulletin of the Korean Chemical Society

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A chromo/fluorogenic NO2S2-macrocycle L functionalized with nitrobenzofurazan unit as a dual-signaling probe was synthesized and structurally characterized by single crystal X-ray analysis. In a cation-induced color change experiment, L exhibited excellent Hg 2+ ion selectivity by showing the color change from orange-red to yellow. However, this hypochromic shift by Hg 2+ was observed for the weaker coordinating anion system such as NO3 -and ClO4 -ions. The observed anion effect is due to the strong coordination of anions inhibits the bond formation between Hg 2+ and the macrocyclic tert-N atom, which is sensitive to induce the color change. In the fluorometric experiment, L showed chelate-enhanced fluorescence change effect only with Hg 2+ ion, together with a change from yellow to green emission. The sensing ability for Hg 2+ with the proposed chemosensor L is due to the stable complexation with 1:1 stoichiometry (metal-toligand).

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“…The plate current (output) therefore becomes a quasi-sigmoidal function of the plate voltage (input). During our early efforts at developing photoionic devices of the 'fluorophore-spacer-receptor' type [29][30][31] based on photoinduced electron transfer (PET), we had learned much from simple pH indicators. 32 One of these lessons was that the optical intensity output varies sigmoidally as the pH input is varied.…”

Section: Mementioning

confidence: 99%

“…99 A closely related format 'receptor1-spacer1-receptor2-fluorophore' is known. 100 Viewed simplistically, 15 contains a tertiary amine to serve as receptor1 and an isoquinoline to serve as receptor2. In fact, the isoquinoline receptor2 is part of an integrated ICT fluorophore in spite of a biaryl twisting.…”

Section: Multi-level Logicmentioning

confidence: 99%

Information gathering and processing with fluorescent molecules

Daly

Ling

Silva

2014

Front. Chem. Sci. Eng.

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Fluorescent photoionic devices with two receptors and two switching mechanisms: applications to pH sensors and implications for metal ion detection

Cited by 73 publications

References 58 publications

A Reversible Dual‐Response Fluorescence Switch for the Detection of Multiple Analytes

A Reversible Dual‐Response Fluorescence Switch for the Detection of Multiple Analytes

A Chromo- and Fluoroionophoric Thiaoxaaza-Macrocycle Functionalized with Nitrobenzofurazan Exhibiting Mercury(II) Selectivity

Information gathering and processing with fluorescent molecules

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