A Chromone-Derived Schiff-Base Ligand as Al3+ “Turn on” Fluorescent Sensor: Synthesis and Spectroscopic Properties

Li, Chao-rui; Qin, Jing-can; Wang, Bi-Dar; Fan, Long; Yan, Jun; Zhou, Yang

doi:10.1007/s10895-015-1720-0

Cited by 24 publications

(8 citation statements)

References 49 publications

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“…To confirm the stoichiometry between sensor and Cu 2+ , the method of continuous variation (Job's plot) was used [30]. During this experimental process, the total concentration of sensor and Cu 2+ was kept constant at 50 μM, with a continuous variable molar fraction of guest [Cu 2+ ]/([sensor] + [Cu 2+ ]).…”

Section: Binding Studiesmentioning

confidence: 99%

A rhodamine-based fluorescent sensor for selective detection of Cu2+ in aqueous media: Synthesis and spectroscopic properties

Abebe

Perkins

Shaw

et al. 2020

Journal of Molecular Structure

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Two new chemosensors, rhodamine B derivative bearing 3-formyl-6-nitrochromone (L 1) and 3formyl-6-methylchromone (L 2) units were designed and synthesized using microwave irradiation for the selective detection of Cu 2+ in aqueous media. Copper triggers the formation of highly fluorescent ring-open spirolactam. The fluorescence intensity was remarkably increased upon the addition of Cu 2+ within a minute, while the other metal ions caused no significant effect. More importantly, the resulting complexes can be used as a reversible fluorescence sensor for CN −. The recognition ability of the sensors was investigated by fluorescence titration, Job's plot, 1 H NMR spectroscopy and density functional theory (DFT) calculations.

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Section: Binding Studiesmentioning

confidence: 99%

A rhodamine-based fluorescent sensor for selective detection of Cu2+ in aqueous media: Synthesis and spectroscopic properties

Abebe

Perkins

Shaw

et al. 2020

Journal of Molecular Structure

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“…According to the basis of 3 σ/k, the detection limit of ITEC was calculated to be 2.19 × 10 −9 mol/L (k=8.861 × 10 8 , σ = 0.647) [38,39],which was lower than those of many reported fluorescence probes for Al 3+ (Table 1). the linear fitting curve with fluorescence intensity of ITEC was plotted in Figure 3b.…”

Section: Sensitivity Of Itec To Al 3+mentioning

confidence: 78%

“…The concentration of Al 3+ (7.41 umol/L) is within this linear range according to WHO regulations on drinking water [34]. According to the basis of 3 σ/k, the detection limit of ITEC was calculated to be 2.19 × 10 −9 mol/L (k = 8.861 × 10 8 , σ = 0.647) [38,39], which was lower than those of many reported fluorescence probes for Al 3+ (Table 1).…”

Section: Sensitivity Of Itec To Al 3+mentioning

confidence: 96%

A New “Turn-On” Fluorescence Probe for Al3+ Detection and Application Exploring in Living Cell and Real Samples

Gao

Zhang

et al. 2019

Applied Sciences

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An excess of Al 3+ will lead to biological disorders and even many diseases. Therefore, detecting the levels of Al 3+ in the human body has drawn great attention for health monitoring. The fluorescence method has been broadly applied because of high sensitivity, real-time detection, and intracellular imaging. In this work, a new probe with "turn-on" fluorescence based on Schiff base derivative, 3,6-imine-triphenylamine-(9-ethyl) carbazole (ITEC), has been successfully synthesized and studied. The high selectivity and sensitivity of ITEC to Al 3+ were verified by fluorescence spectra and the detection limit was 2.19 nmol/L. A 1:2 stoichiometry of ITEC-Al 3+ was obtained by the 1 H NMR spectra and Job's plot. Furthermore, ITEC was successfully applied to the detection of Al 3+ with different concentrations in living HeLa cells. The analog experiments about nature contamination of Al 3+ in cells and real samples were finished.Currently, Schiff bases compounds are vastly recognized as fluorescence probes for metal ions with the high sensitivity, good selectivity, and high excitation coefficients, but a lot of them displayed fluorescence "on-off" behavior [24][25][26], which is a disadvantage for the visualization study. In recent years, a few "off-on" fluorescence probes have been developed, but the probes applied to detect Al 3+ in living cells and real samples were scarce [27][28][29][30]. Hence, it is very meaningful to develop "off-on" probes for Al 3+ monitoring in real application [31].In this manuscript, we reported a feasible method to synthesize a novel Schiff base, 3,6-imine-triphenylamine-(9-ethyl) carbazole (ITEC), as a "turn-on" fluorescence probe for selective detection of Al 3+ . The ITEC was further applied to detect Al 3+ in living cells. In addition, the experiments of Al 3+ detection in the real sample have been carried out. Experimental Materials and InstrumentationCarbazole, triphenylamine, and Palladium/C catalysts were purchased from Aladdin. All other experimental materials were derived from the local commercial suppliers. All materials were not further purified. 1 H NMR spectra were measured on a Bruker Avance 400 spectrometer. The electrospray ionization (ESI) mass spectra were recorded using an Agilent-6510-Q-TOF spectrometer. A UV-3600 spectrophotometer and a Thermo Scientific Nicolet IS10 Spectrometer were used to measure the UV-visible absorption spectra and Infrared spectra. Fluorescence spectra were obtained using a Hitachi F-7000 Fluorescence Spectrophotometer. The fluorescence images in living cells were obtained by an Olympus FV300 confocal microscope. Synthesis of ITECIntermediates M1-M4 were synthesized according to the literature reports [32,33] and the detailed procedures were described in supporting information. The synthesis of 3,6-imine-triphenylamine-(9-ethyl) carbazole (ITEC) is shown in Scheme 1. Scheme 1. The synthesis route of 3,6-imine-triphenylamine-(9-ethyl) carbazole (ITEC).

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“…Due to their structure flexibility and strong coordination capabilities, they are extensively used in the field of coordination chemistry. They coordinate through the nitrogen atom of the azomethine group and the oxygen atom of the deprotonated phenolic group [14]. Due to their multiple biological activities such as antibacterial, antitumor, insecticidal, anticancer, anticonvulsant, anti-inflammatory, and cytotoxicity, as prodrugs, in the strengthening of immune response against cancer, in HIV, and in leukemia, Schiff bases have been studied intensively over the past few decades [15].…”

Section: Introductionmentioning

confidence: 99%

Schiff-Based Fluorescent-ON Sensor L Synthesis and Its Application for Selective Determination of Cerium in Aqueous Media

et al. 2020

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In the present study, a fluorescent sensor L for sensing of Ce3+ ion was designed and characterized by XRD, 1HNMR, and FTIR. Its fluorescence behavior towards metal ion was examined by fluorescence spectroscopy. Chelation-enhanced fluorescence was shown by the sensor L upon interaction with Ce3+ ion. This fluorescent sensor exhibits high sensitivity and selectivity towards Ce3+ ion in acetonitrile solution, forming 2 : 1 (L : M) complex as determined by Job’s plot. Association constant was found to be 1×107 M−1 estimated from the Benesi-Hildebrand plot. No significant interference was observed in the presence of other studied alkali, alkaline, and transition metal ions. A rapid response was observed when employed for the determination of Ce3+ ion in spiked water samples with a limit of detection equal to 3.4×10−8 M.

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A Chromone-Derived Schiff-Base Ligand as Al3+ “Turn on” Fluorescent Sensor: Synthesis and Spectroscopic Properties

Cited by 24 publications

References 49 publications

A rhodamine-based fluorescent sensor for selective detection of Cu2+ in aqueous media: Synthesis and spectroscopic properties

A rhodamine-based fluorescent sensor for selective detection of Cu2+ in aqueous media: Synthesis and spectroscopic properties

A New “Turn-On” Fluorescence Probe for Al3+ Detection and Application Exploring in Living Cell and Real Samples

Schiff-Based Fluorescent-ON Sensor L Synthesis and Its Application for Selective Determination of Cerium in Aqueous Media

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