Colorimetric Signaling of Water Content in Acetonitrile by Phenolic Dye-Fluoride Complexes

Moon, Jung Ok; Kim, Youn Hwan; Choi, Myung Gil; Chang, Suk‐Kyu

doi:10.5012/bkcs.2011.32.9.3517

Cited by 26 publications

(12 citation statements)

References 28 publications

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“…Competition with water in a reversible acid-base reaction led to effective two-component coumarin phenylsemicarbazone/anion optical chemosensors. Despite the fact their sensing mechanism is based on an acid-base equilibrium, they can be classified as “competitive ligand-based” chemosensors, similar to the quinoline or phenolic dyes published by Kim et al and Moon et al, respectively, with detection limits of 0.16–0.17 wt % [ 10 , 26 ]. Determined detection limits (LOD) for water by the studied phenylsemicarbazones were amongst the lowest detection limits published in the literature and they can compete in sensitivity with chemodosimeters (LOD: 0.0016–0.0026 wt %) [ 25 ].…”

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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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%

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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“…However, dye 2 strongly interacted with fluoride ions and formed a more stable 1:2 stoichiometric complex, much like other sensitive fluoride sensing phenolic dyes. 12 This difference was also noted upon addition of water. The hydrogen bonding in the 1-F system was easily broken by water and the color returned to the original with~3% water content, while the color of the 2-F system continuously changed until a water content of more than 20% was present.…”

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confidence: 68%

“…This colorimetric behavior is known to a result from the formation of hydrogen bonds between the hydroxyl group on the dyes and added fluoride ions, which is disrupted by water molecules. 12 However, the chromogenic behavior of 1 differed from that of 2. In the THF solution, dye 1 seemed to interact weakly with fluoride ions, as the color changes were not complete until about 20 equiv of fluoride was added.…”

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confidence: 96%

“…10,11 Recently, a potential use of fluoride sensing phenolic dyes to determine water content in organic solvents was reported based on the competition between water molecules and fluoride ions for hydrogen bonding with the hydroxyl group of the dye. 12 The water content in an organic solvent was sensitively determined using ratiometric responses of ultraviolet-visible (UV-vis) absorption bands as well as colorimetric signaling by a naked-eye detectable color change of the phenolic dyefluoride ion complexes.…”

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confidence: 99%

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Determination of Water Content in THF Based on Chemical Shift Differences in Solution NMR

Jun

Park

Lee

et al. 2016

Bulletin Korean Chem Soc

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“…For instance, a simple chromogenic signaling system based on phenolic dye‐fluoride complexes for water content in acetonitrile was developed by Moon et al . (LOD=0.17 %) . In addition, Kim et al .…”

Section: Resultsmentioning

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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Colorimetric Signaling of Water Content in Acetonitrile by Phenolic Dye-Fluoride Complexes

Cited by 26 publications

References 28 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

Determination of Water Content in THF Based on Chemical Shift Differences in Solution NMR

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

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