Selective fluorescent sensor for mercury ions in aqueous media using a 1,4-dihydropyridine derivative

Homraruen, Daranee; Sirijindalert, Thirawat; Dubas, Luxsana; Sukwattanasinitt, Mongkol; Ajavakom, Anawat

doi:10.1016/j.tet.2012.11.094

Cited by 24 publications

(12 citation statements)

References 45 publications

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“…[26][27][28][29][30][31] The glucopyranosyl group was incorporated to increase the water solubility of the DHP triethylester, without having to hydrolyze it to the tricarboxylic acid, as this was found to reduce its fluorescence quantum yield. 34 The systematic study of this Glc-DHP yielded a new highly sensitive TNP sensor with a capability for quantitative determination of TNP, 2,4-dinitrophenol (DNP), and 4-nitrophenol (4NP) in water samples.…”

Section: Introductionmentioning

confidence: 99%

Glucopyranosyl-1,4-dihydropyridine as a new fluorescent chemosensor for selective detection of 2,4,6-trinitrophenol

Pinrat

Boonkitpatarakul

Paisuwan

et al. 2015

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Glucopyranosyl-1,4-dihydropyridine (Glc-DHP) was synthesized as a new fluorescent chemosensor via cyclotrimerization of the β-amino acrylate in the presence of TiCl4. This DHP derivative is soluble in aqueous medium and the solution gives a blue fluorescence signal with a quantum yield of 29%. The fluorescence signal of Glc-DHP was selectively quenched by 2,4,6-trinitrophenol (TNP) with a quenching coefficient (Ksv) of 4.47 × 10(4) and at one of the best reported detection limits of 0.94 μM. The quenching mechanism was confirmed to be of the static type at the low concentration region (less than 50 μM) with the significant quenching effect of competitive absorption starting from the concentration of 50 μM. Even in the real sample (seawater and industrial water), the quenching efficiencies of TNP on the fluorescence emission of Glc-DHP were proven to be at the same level with that of the test in pure water, demonstrating the practicability of the detection. Furthermore, a fluorescent paper sensor could be prepared by immersing the paper into the Glc-DHP solution. The fluorescence of the paper sensor disappeared either by writing with TNP solution or by exposure to TNP vapor. This detection could be observed by the naked eye under black light. The pH effect was proven to be a substantial factor in the quenching mechanism, providing an accurate determination of TNP, 2,4-dinitrophenol (DNP) and 4-nitrophenol (4NP) in real mixed-samples.

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Section: Introductionmentioning

confidence: 99%

Glucopyranosyl-1,4-dihydropyridine as a new fluorescent chemosensor for selective detection of 2,4,6-trinitrophenol

Pinrat

Boonkitpatarakul

Paisuwan

et al. 2015

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“…In recent years, 1,4‐dihydropyridine‐based fluorescent molecules have received increasing attention because of their simple structures, easy syntheses, excellent photophysical properties, and extensive applications in fluorescent sensors . Importantly, some 1,4‐dihydropyridine derivatives reportedly exhibit outstanding AIE properties and emit good solid‐state fluorescence upon a simple structural modification.…”

Section: Introductionmentioning

confidence: 99%

“…In recent years, 1,4-dihydropyridine-based fluorescent molecules have received increasing attention because of their simple structures, easy syntheses, excellent photophysical properties, and extensive applications in fluorescent sensors. [12][13][14][15][16][17][18] Importantly,s ome1 ,4-dihydropyridined erivatives reportedly exhibit outstanding AIE properties and emit good solid-state fluorescenceu pon as imple structuralm odification. Specifically,anappropriate structuralunit introduced on the nitrogena tom of the 1,4-dihydropyridine ring can lead to twisted molecular conformations.…”

Section: Introductionmentioning

confidence: 99%

Aggregation‐Induced Emission‐Active 1,4‐Dihydropyridine‐Based Dual‐Phase Fluorescent Sensor with Multiple Functions

Zhou

Chen

Duan

et al. 2019

Chemistry An Asian Journal

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A N‐2‐phenylethyl‐substituted 1,4‐dihydropyridine derivative (NDHP) containing 5,5‐dimethylcyclohexane‐1,3‐dione and naphthylethylene was designed and synthesized. NDHP acts as a multifunctional fluorescent sensor in dual phases. The crystal structure analysis confirms that the NDHP molecules have highly twisted conformations. The twisted conformation results in aggregation‐induced emission properties and solid‐state emission, by restricting the intramolecular free rotation in the aggregated or solid state. In the solid state, NDHP exhibits reversible mechanochromic properties as a result of the transition between the amorphous and crystalline states. NDHP also exhibits a rare phenomenon of acid‐fumed solid‐state emission enhancement owing to the change in packing mode from a zigzag arrangement to J‐aggregation. The solid‐state stimuli‐responsive fluorescence switching is applied to realize a rewritable optical recording media and a multiple output combinational logic system. In solution, NDHP shows a selective fluorescence response for environmentally harmful Hg2+, with a limit of detection of 2.7 nm. This results from the “turn‐on” responsive behavior owing to the Hg2+‐triggered aggregation of the NDHP molecules. NDHP is also used in the imaging of intracellular Hg2+ in HeLa cells. These findings provide a feasible and attractive route for developing multifunctional fluorescent sensors for use in dual phases.

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“…[10][11][12][13] Out of the reported methods for detection of Hg 2+ , colorimetric and fluorometric methods offer numerous advantages in terms of high selectivity, sensitivity, time efficiency and direct visual detection. [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28] Thus, much effort has been devoted in the fabrication of new sensitive and selective methods for determination of toxic mercury.…”

Section: Introductionmentioning

confidence: 99%

“…Recently, number of fluorescent probes for Hg 2+ detection have been reported, [14][15][16][17][18][19][20][21][22][23][24][25][26][27][28] where the majority of the probes work with a "fluorescence off" (fluorescence quenching) and "fluorescence on" (fluorescence enhancement) mechanism. Moreover, these probes work efficiently in organic solvents or mixed solution of organic solvent-water which limits their application in biological and environmental samples.…”

Section: Introductionmentioning

confidence: 99%

Fluorometric sensing of Hg2+ ions in aqueous medium by nano-aggregates of a tripodal receptor

et al. 2014

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Two new tripodal receptors (1–2) have been synthesized and characterized by various spectroscopic techniques. The nano-aggregates of 1 and 2 (N1 and N2) have been prepared by a re-precipitation method in aqueous medium and have shown different photo-physical properties. Nano-aggregates of 1 (N1) can selectively recognize Hg(2+) in aqueous medium in the presence of other metal ions with enhancement in fluorescent intensity. The response was linearly proportional to the concentration of Hg(2+) in the range 0–10 μM with a detection limit of 2.4 nM. The mechanism of selective binding of Hg(2+) by N1 has also been supported by theoretical studies. To the best of our knowledge, this work represents the first report on substituted thiourea based nano-aggregates for nano-molar detection of mercury in aqueous medium.

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Selective fluorescent sensor for mercury ions in aqueous media using a 1,4-dihydropyridine derivative

Cited by 24 publications

References 45 publications

Glucopyranosyl-1,4-dihydropyridine as a new fluorescent chemosensor for selective detection of 2,4,6-trinitrophenol

Glucopyranosyl-1,4-dihydropyridine as a new fluorescent chemosensor for selective detection of 2,4,6-trinitrophenol

Aggregation‐Induced Emission‐Active 1,4‐Dihydropyridine‐Based Dual‐Phase Fluorescent Sensor with Multiple Functions

Fluorometric sensing of Hg2+ ions in aqueous medium by nano-aggregates of a tripodal receptor

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