Water detection in organic solvents using a copolymer membrane immobilised with a fluorescent intramolecular charge transfer-type dye: effects of intramolecular hydrogen bonds

Morimoto, Ami; Shimizu, Kei; Suzuki, Naoya; Yagi, Shigeyuki; Sueyoshi, Kenji; Endo, Tatsuro; Hisamoto, Hideaki

doi:10.1039/d3an02165c

Cited by 3 publications

(1 citation statement)

References 56 publications

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“…It can be seen from the nuclear magnetic titration data that the Schiff base RS- 4 formed relatively slowly, which is inconsistent with the rapid increase in fluorescence. Therefore, only intermolecular charge transfer occurred in the process of fluorescence recognition, and a Schiff base was not quickly generated (the mechanism is shown in Figure 12 ) [ 33 , 34 ].…”

Section: Resultsmentioning

confidence: 99%

The Intramolecular Charge Transfer Mechanism by Which Chiral Self-Assembled H8-BINOL Vesicles Enantioselectively Recognize Amino Alcohols

Wang,

Song,

Wei

et al. 2024

IJMS

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The chiral H8-BINOL derivatives R-1 and R-2 were efficiently synthesized via a Suzuki coupling reaction, and they can be used as novel dialdehyde fluorescent probes for the enantioselective recognition of R/S-2-amino-1-phenylethanol. In addition, R-1 is much more effective than R-2. Scanning electron microscope images and X-ray analyses show that R-1 can form supramolecular vesicles through the self-assembly effect of the π-π force and strong hydrogen bonding. As determined via analysis, the fluorescence of the probe was significantly enhanced by mixing a small amount of S-2-amino-1-phenylethanol into R-1, with a redshift of 38 nm, whereas no significant fluorescence response was observed in R-2-amino-1-phenylethanol. The enantioselective identification of S-2-amino-1-phenylethanol by the probe R-1 was further investigated through nuclear magnetic titration and fluorescence kinetic experiments and DFT calculations. The results showed that this mechanism was not only a simple reactive probe but also realized object recognition through an ICT mechanism. As the intramolecular hydrogen bond activated the carbonyl group on the probe R-1, the carbonyl carbon atom became positively charged. As a strong nucleophile, the amino group of S-2-amino-1-phenylethanol first transferred the amino electrons to a carbonyl carbocation, resulting in a significantly enhanced fluorescence of the probe R-1 and a 38 nm redshift. Similarly, S-2-amino-1-phenylethanol alone caused severe damage to the self-assembled vesicle structure of the probe molecule itself due to its spatial structure, which made R-1 highly enantioselective towards it.

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Section: Resultsmentioning

confidence: 99%

The Intramolecular Charge Transfer Mechanism by Which Chiral Self-Assembled H8-BINOL Vesicles Enantioselectively Recognize Amino Alcohols

Wang,

Song,

Wei

et al. 2024

IJMS

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Water Content Sensing in Organic Solvents Using Capillary Sensor Immobilizing Intramolecular Charge Transfer-type Dyes

MORIMOTO,

SUEYOSHI,

ENDO

et al. 2024

BUNSEKI KAGAKU

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Nitrogen and Sulfur Co-Doped Graphene-Quantum-Dot-Based Fluorescent Sensor for Rapid Visual Detection of Water Content in Organic Solvents

Zhang,

Wang,

et al. 2024

Molecules

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Accurate water content detection is crucial for optimizing chemical reactions, ensuring product quality in pharmaceutical manufacturing, and maintaining food safety. In this study, nitrogen and sulfur co-doped graphene quantum dots (R-GQDs) were synthesized via a one-step hydrothermal method using o-phenylenediamine as the carbon source. The synthesis conditions, including reaction time, temperature, o-phenylenediamine concentration, and H2SO4/water ratio, were optimized using the Box-Behnken response surface methodology. The R-GQDs exhibited excellent fluorescence stability and distinct solvent-dependent characteristics, alongside a broad linear detection range and high sensitivity, making them highly suitable for dual-mode water content detection (colorimetric and fluorescent). To enhance the accuracy of visual detection, R-GQDs were incorporated into portable test strips with smartphone-assisted analysis, compensating for the human eye’s limitations in distinguishing subtle color changes. The sensor’s practical utility was validated through spiked recovery experiments in food samples, and the R-GQDs demonstrated good biocompatibility for in vivo imaging in shrimp. These findings highlight a novel strategy for developing portable, real-time water content sensors with potential applications in both portable detection systems and biological imaging.

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Water detection in organic solvents using a copolymer membrane immobilised with a fluorescent intramolecular charge transfer-type dye: effects of intramolecular hydrogen bonds

Abstract: Numerous fluorescent dye-based optical sensors have been developed to detect water in organic solvents. However, only a few such sensors can detect water in polar solvents such as methanol or...

Cited by 3 publications

References 56 publications

The Intramolecular Charge Transfer Mechanism by Which Chiral Self-Assembled H8-BINOL Vesicles Enantioselectively Recognize Amino Alcohols

The Intramolecular Charge Transfer Mechanism by Which Chiral Self-Assembled H8-BINOL Vesicles Enantioselectively Recognize Amino Alcohols

Water Content Sensing in Organic Solvents Using Capillary Sensor Immobilizing Intramolecular Charge Transfer-type Dyes

Nitrogen and Sulfur Co-Doped Graphene-Quantum-Dot-Based Fluorescent Sensor for Rapid Visual Detection of Water Content in Organic Solvents

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