Site-Selective Imination of an Anthracenone Sensor: Selective Fluorescence Detection of Barium(II)

Basa, Prem N.; Bhowmick, Arundhati; Schulz, Mariah M.; Sykes, Andrew G.

doi:10.1021/jo2013143

Cited by 54 publications

(41 citation statements)

References 48 publications

(28 reference statements)

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“…2) The propensity of C=N bond to photoisomerization opens up a non-radiative relaxation pathway. [49][50][51] Both factors may be alleviated through metal coordination at the imino nitrogen, which is described in Section 2.9.…”

Section: Fluorescence Quantum Yieldmentioning

confidence: 99%

Tunable Dual Fluorescence of 3‐(2,2′‐Bipyridyl)‐Substituted Iminocoumarin

Younes¹,

Zhu²

2012

ChemPhysChem

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3-(2,2'-Bipyridyl)-substituted iminocoumarin molecules (compounds 1 and 2) exhibit dual fluorescence. Each molecule has one electron donor and two electron acceptors that are in conjugation, which leads to fluorescence from two independent charge transfer (CT) states. To account for the dual fluorescence, we subscribe to a kinetic model in which both CT states form after rapid decays from the directly accessed S(1) and S(2) excited states. Due to the slow internal conversion from S(2) to S(1), or more likely the slow interconversion between the two subsequently formed CT states, dual emission is allowed to occur. This hypothesis is supported by the following evidence: 1) the emission at short and long ends of the spectrum originates from two different excitation spectra, which eliminates the possibility that dual emission occurs after an adiabatic reaction at the S(1) level. 2) The fluorescence quantum yield of compound 2 grows with increasing excitation wavelength, which indicates that the high-energy excitation elevates the molecule to a weakly emissive state that does not internally convert to the low-energy, highly emissive state. The intensity of the two emission bands of 1 is tunable through the specific interactions between either of the two electron acceptors with another species, such as Zn(2+) in the current demonstration. Therefore, the development of ratiometric fluorescent indicators based on the dual-emitting iminocoumarin system is conceivable. Further fundamental studies on this series of compounds using time-resolved spectroscopic techniques, and explorations of their applications will be carried out in the near future.

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Section: Fluorescence Quantum Yieldmentioning

confidence: 99%

Tunable Dual Fluorescence of 3‐(2,2′‐Bipyridyl)‐Substituted Iminocoumarin

Younes¹,

Zhu²

2012

ChemPhysChem

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“…12 Selective reduction of the internal carbonyl was achieved using 1.0 equiv of NaBH 4 in aqueous ethanolic solution. Only the more electronegative carbonyl group is reduced leaving the imine group unreacted, even when reduced over a lengthy period of time (15 h).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

Differential Sensing of Zn(II) and Cu(II) via Two Independent Mechanisms

Basa

Sykes

2012

J. Org. Chem.

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Selective reduction of an anthracenone-quinoline imine derivative, 2, using 1.0 equiv of NaBH(4) in 95% ethanol affords the corresponding anthracen-9-ol derivative, 3, as confirmed by (1)H NMR, (13)C NMR, ESI-MS, FTIR, and elemental analysis results. UV-vis and fluorescence data reveal dramatic spectroscopic changes in the presence of Zn(II) and Cu(II). Zinc(II) coordination induces a 1,5-prototropic shift resulting in anthracene fluorophore formation via an imine-enamine tautomerization pathway. Copper(II) induces a colorimetric change from pale yellow to orange-red and results in imine hydrolysis in the presence of water. Spectroscopic investigations of metal ion response, selectivity, stoichiometry, and competition studies all suggest the proposed mechanisms. ESI-MS analysis, FTIR, and single-crystal XRD further support the hydrolysis phenomenon. This is a rare case of a single sensor that can be used either as a chemosensor (reversibly in the case of Zn(II)) or as a chemodosimeter (irreversibly in the case of Cu(II)); however, the imine must contain a coordinating Lewis base, such as quinoline, to be active for Cu(II).

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“…When tested with barium(II) titration in acetonitrile, a linear increase was seen in fluorescence intensity going from 0–133 µM (0 ppm to 18 ppm), after which the sensor molecule saturated. Although there are no other analytical data available, this sensor shows potential for the detection of barium(II) in aqueous media [51].…”

Section: Analytesmentioning

confidence: 99%

Metal Cation Detection in Drinking Water

Dalmieda

Kruse

2019

Sensors

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Maintaining a clean water supply is of utmost importance for human civilization. Human activities are putting an increasing strain on Earth’s freshwater reserves and on the quality of available water on Earth. To ensure cleanliness and potability of water, sensors are required to monitor various water quality parameters in surface, ground, drinking, process, and waste water. One set of parameters with high importance is the presence of cations. Some cations can play a beneficial role in human biology, and others have detrimental effects. In this review, various lab-based and field-based methods of cation detection are discussed, and the uses of these methods for the monitoring of water are investigated for their selectivity and sensitivity. The cations chosen were barium, cadmium, chromium, copper, hardness (calcium, magnesium), lead, mercury, nickel, silver, uranium, and zinc. The methods investigated range from optical (absorbance/fluorescence) to electrical (potentiometry, voltammetry, chemiresistivity), mechanical (quartz crystal microbalance), and spectrometric (mass spectrometry). Emphasis is placed on recent developments in mobile sensing technologies, including for integration into microfluidics.

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Site-Selective Imination of an Anthracenone Sensor: Selective Fluorescence Detection of Barium(II)

Cited by 54 publications

References 48 publications

Tunable Dual Fluorescence of 3‐(2,2′‐Bipyridyl)‐Substituted Iminocoumarin

Tunable Dual Fluorescence of 3‐(2,2′‐Bipyridyl)‐Substituted Iminocoumarin

Differential Sensing of Zn(II) and Cu(II) via Two Independent Mechanisms

Metal Cation Detection in Drinking Water

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