Chromogenic signalling of water content in organic solvents by hydrazone–acetate complexes

Kim, Youn Hwan; Choi, Myung Gil; Im, Hyun Gyu; Ahn, Sangdoo; Shim, Il-Wun; Chang, Suk‐Kyu

doi:10.1016/j.dyepig.2011.07.019

Cited by 50 publications

(20 citation statements)

References 34 publications

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“…A qualitative and quantitative detection of low-level water present as an impurity in organic solvents has great significance in several fields of chemistry and industry processes (pharmaceutical manufacturing, food processing, production of anhydrous solvents and chemical reagents, petroleum fuel industry, paper production and biomedical or environmental monitoring) [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 ]. Many analytical approaches and techniques have been established for the determination of water in a wide variety of organic solvents, such as Karl Fischer titration and gas chromatography methods on the laboratory scale, and electrochemical/electrophysical methods particularly for large-scale industry processes.…”

Section: Introductionmentioning

confidence: 99%

“…However, electrical sensors suffer often from the lack of insufficient portability/precision and exhibit undesirable sensitivity to electromagnetic interference [ 4 ]. Laboratory methods have the disadvantage of requiring time-consuming sample preparation, inability of real-time monitoring of the water content, a need for skilled personnel and special equipment and interference from other co-existing species [ 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 , 11 , 12 , 13 , 14 , 15 , 16 , 17 , 18 , 19 , 20 , 21 , 22 , 23 ]. Moreover, the Karl–Fisher titration is less sensitive in aprotic and non-alcoholic solvents [ 19 ].…”

Section: Introductionmentioning

confidence: 99%

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7-Dialkylaminocoumarin Oximates: Small Molecule Fluorescent “Turn-On” Chemosensors for Low-Level Water Content in Aprotic Organic Solvents

et al. 2017

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The water sensing properties of two efficient two-component fluorescent “turn-on” chemo-sensors based on the 7-dialkylaminocoumarin oxime acid-base equilibrium were investigated. Interestingly, although simple frontier orbital analysis predicts an intramolecular photoinduced electron transfer quenching pathway in conjugated oximates, TD-DFT (Time-dependent density functional theory) quantum chemical calculations support non-radiative dark S1 excited state deactivation as a fluorescence quenching mechanism. Due to the acid-base sensing mechanism and sensitive “turn-on” fluorescent response, both studied coumarin aldoxime chemosensors exhibit rapid response to low-level water content in polar aprotic solvents, with detection limits comparable to chemodosimeters or chemosensors based on interpolymer π-stacking aggregation.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

7-Dialkylaminocoumarin Oximates: Small Molecule Fluorescent “Turn-On” Chemosensors for Low-Level Water Content in Aprotic Organic Solvents

et al. 2017

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“…In addition, Kim et al . have reported detection limits of the anthracene‐based hydrazone‐acetate system for determination of the water content in acetonitrile and tetrahydrofuran as 0.037 and 0.071 %, respectively . Previously, we have also developed a chromogenic system for the detection of water content in acetontrile (LOD=0.012 %) based on protonation and deprotonation .…”

Section: Resultsmentioning

confidence: 99%

“…Recently, anion receptors have been utilized in the colorimetric detection of water in organic solvents . In these systems, the colorimetric receptor for water is prepared by the addition of anions in the solution of anion receptors.…”

Section: Introductionmentioning

confidence: 99%

The Colorimetric Signaling of Water Content by a Deprotonated Schiff Base in some Aprotic Organic Solvents

et al. 2020

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A simple Schiff base, (E)-2-[1-{2-(2,4-dinitrophenyl)hydrazono} ethyl]phenol (Hdph) and its deprotonated form, (E)-1-(2,4dinitrophenyl)-2-{1-(2-hydroxyphenyl)ethylidene} hydrazine-1ide (dph) have been synthesized and characterized by various physicochemical and spectroscopic techniques. Their structures have also been determined by single-crystal X-ray crystallography. The dph has been utilized as a colorimetric probe for the signaling of water content in some water-miscible aprotic organic solvents (acetonitrile and tetrahydrofuran). The dph reveals a pronounced colorimetric behavior in response to the variation of water content in these solvents. Significant changes in UV-visible absorption spectra permit a ratiometric analysis of the signaling behavior. The spectral changes are pronounced for the water content of less than 10 %, which is suitable for the application of dph as a receptor for the determination of water content in binary aqueous organic solvents having lower water content. The limit of detection (LOD) for water content in acetonitrile and tetrahydrofuran is calculated as 0.20 % and 0.28 %, respectively.

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“…Owing to the hydrogen bonding interaction, the recognition and/or sensing of the anions was performed in noncompetitive organic solvents such as acetonitrile and DMSO. 24 In aqueous solution, the hydrogen bonding interaction between the hydrazone and analytes was significantly weakened due to the presence of competing water molecules. Figure 10 shows the absorption response of Figure 8.…”

Section: Chemosensing Applicationsmentioning

confidence: 99%

Hydrazone derivatives appended to diphenylphosphine oxide as anion sensors

2017

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Phosphine substituted hydrazones with or without nitro substituents were synthesized and characterized by multinuclear NMR, FT-IR, UV-Vis spectroscopy and single crystal X-ray diffraction. The anion recognition properties of phosphine oxides {Ph 2 P(O)C 6 H 4 CHNNHPh} (2) and {Ph 2 P(O)C 6 H 4 CHNNHC 6 H 3 (2,4-NO 2) 2 } (4) with anions (F − , Cl − , Br − , I − , CH 3 COO − and H 2 PO − 4) were investigated. The selectivity towards these anions is attributed to the hydrogen bonding capability of the NH bond. Competitive titrations have shown that the binding ability of fluoride with 4 is not influenced by the presence of other anions.

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Chromogenic signalling of water content in organic solvents by hydrazone–acetate complexes

Cited by 50 publications

References 34 publications

7-Dialkylaminocoumarin Oximates: Small Molecule Fluorescent “Turn-On” Chemosensors for Low-Level Water Content in Aprotic Organic Solvents

7-Dialkylaminocoumarin Oximates: Small Molecule Fluorescent “Turn-On” Chemosensors for Low-Level Water Content in Aprotic Organic Solvents

The Colorimetric Signaling of Water Content by a Deprotonated Schiff Base in some Aprotic Organic Solvents

Hydrazone derivatives appended to diphenylphosphine oxide as anion sensors

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