Tetraphenylethene-substituted benzothiadiazoles: AIE and TICT properties, tunable intramolecular conjugation and application in detecting trace water in organic solvents

Sun, Hao; Tang, Xinxue; Zhang, Ran; Sun, Wenhao; Miao, Bao-Xi; Zhao, Yun; Ni, Zhong‐Hai

doi:10.1016/j.dyepig.2019.108051

Cited by 44 publications

(16 citation statements)

References 38 publications

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“…Tetraphenylethylene based benzothiadiazole derivatives (27) were reported by H. Sun et al. [48] The quantitative water detection in THF, dioxane, and ethyl acetate was performed for ortho, meta, and para derivatives. These compounds exhibit solvatochromism and on-off emission behavior due to the combined action of AIE and TICT.…”

Section: Probes Based On Solvatochromismmentioning

confidence: 99%

Chemical Sensors for Water Detection in Organic Solvents and their Applications

Kumar

Ghosh

2021

ChemistrySelect

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Moisture or trace water detection at a very low level in organic solvents and other chemical reagents has great significance in the chemical and industrial process. At present, reports on chemical sensors for moisture are still in the early development phase and need continuous improvements. Recently, several approaches have been proposed for the easier detection of water content in the organic solvents. In this review article, we have summarized recent reports on chemical sensors used to detect water in organic solvents. The discussion is focused on optical methods, including fluorescent and colorimetric probes exploring solvatochromism, displacement of ligand or metal and water-induced protonation. Besides, water detection in organic solvents by NMR spectroscopy is also discussed. Probe structure, sensitivity with organic solvents, spectroscopy detection limits, and possible application in various other research areas, including ink-less writing, sweat pore mapping, food products and engineering materials are described in detail.

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Section: Probes Based On Solvatochromismmentioning

confidence: 99%

Chemical Sensors for Water Detection in Organic Solvents and their Applications

Kumar

Ghosh

2021

ChemistrySelect

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“…Molecular 2,1,3-benzothiadiazole (BTD) derivatives have been successfully applied as bioimaging probes. − Several groups − have effectively tested the BTD derivatives as active and efficient bioprobes for bioimaging experiments, including us. − In spite of the successes renowned on the use of BTD luminophores, there is still much room for improvement and this new class of fluorophores has just begun to glow among the classical scaffolds, − such as coumarins, fluoresceins, cyanines, rhodamines, BODIPYs, and a few others. A small number of reports have investigated the AIEE (or AIE) effect for fluorescent BTD derivatives (see examples in Figure ), − but these studies are in general not focused to depict the dynamics (formation/break and intramolecular interactions) of this phenomenon and only a few properties (size and standard photophysical) of the organic nanoaggregates are routinely described.…”

Section: Introductionmentioning

confidence: 99%

Deciphering the Dynamics of Organic Nanoaggregates with AIEE Effect and Excited States: Lipophilic Benzothiadiazole Derivatives as Selective Cell Imaging Probes

Sodre

Guido

Souza³

et al. 2020

J. Org. Chem.

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An aggregation-induced emission enhancement (AIEE) effect in fluorescent lipophilic 2,1,3-benzothiadiazole (BTD) derivatives and their organic nanoaggregates were studied. A set of techniques such as single-crystal X-ray, dynamic light scattering (DLS), electron paramagnetic resonance (EPR), UV−vis, fluorescence, and density functional theory (DFT) calculations have been used to decipher the formation/break (kinetics), properties, and dynamics of the organic nanoaggregates of three BTD small organic molecules. An in-depth study of the excited-state also revealed the preferential relaxation emissive pathways for the BTD derivatives and the dynamics associated with it. The results described herein, for the first time, explain the formation of fluorescent BTD nanoaggregate derivatives and allow for the understanding of their dynamics in solution as well as the ruling forces of both aggregation and break processes along with the involved equilibrium. One of the developed dyes could be used at a nanomolar concentration to selectively stain lipid droplets emitting an intense and bright fluorescence at the red channel. The other two BTDs could also stain lipid droplets at very low concentrations and were visualized preferentially at the blue channel.

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“…It is considered as a gold standard for water content measurements according to multiple publications. [13][14][15][16] ASTM International (ASTM) also published a standard test method for water in organic liquids by coulometric KF. 17 However, it is a destructive technique, requires a specic reagent, and takes considerable time for one measurement.…”

Section: Introductionmentioning

confidence: 99%