Interaction of water with a benzimidazole derivative: fluorescence and colorimetric recognition of trace level water involving intra‐molecular charge transfer process

Nandi, Sandip; Mandal, S. C.; Sanmartín‐Matalobos, Jesús; Sahana, Animesh

doi:10.1002/jmr.2488

Cited by 11 publications

(4 citation statements)

References 44 publications

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“…The main emission around 500 nm shows a slight red-shift as the solvent polarity increases because of the intramolecular charge transfer (ICT) of the Tz moiety with the phenyl group as a donor and the triazine as an acceptor. 41 The Tz ligand also exhibits the same red-shift phenomenon (Figure S16). In addition, TzDa possesses intramolecular hydrogen bonding interactions between the OH on Da and the generated CN bond.…”

Section: ■ Experimental Sectionmentioning

confidence: 71%

“…The prepared TzDa gives absorption peaks at 365 and 425 nm, and shows two main fluorescence emissions around 500 and 590 nm in common organic solvents (Figure a and Figure S15). The main emission around 500 nm shows a slight red-shift as the solvent polarity increases because of the intramolecular charge transfer (ICT) of the Tz moiety with the phenyl group as a donor and the triazine as an acceptor . The Tz ligand also exhibits the same red-shift phenomenon (Figure S16).…”

Section: Resultsmentioning

confidence: 93%

See 1 more Smart Citation

High-Crystallinity Covalent Organic Framework with Dual Fluorescence Emissions and Its Ratiometric Sensing Application

Qian

Dai

Yang

et al. 2017

ACS Appl. Mater. Interfaces

248

146

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High crystallinity of covalent organic frameworks (COFs) with dual fluorescence emissions has not been reported so far. Here, we show the rational design and preparation of high-crystallinity COF TzDa via the synergetic interaction of docking sites and hydrogen bonds: 4,4',4″-(1,3,5-Triazine-2,4,6-triyl)trianiline (Tz) with the docking site and 2,5-dihydroxyterephthalaldehyde (Da) with the OH group are employed to synthesize the imine-linked two-dimensional high-crystallinity layered structure TzDa. The prepared mesoporous TzDa (ca. 36 Å) exhibits high thermal and chemical stability. The intramolecular charge transfer (ICT) and excited-state intramolecular proton transfer (ESIPT) effects bring TzDa two main fluorescence emissions around 500 and 590 nm. Water molecules can interfere with the ICT and ESIPT effects, allowing the development of a ratiometric fluorescent sensor for water in organic solvents. The proposed sensor shows high sensitivity to trace water in conventional organic solvents. The high stability of TzDa allows its recyclable uses for trace water detection. This work not only offers a platform for the construction of high-crystallinity COFs, but also provides a rational design of COFs with dual fluorescence emissions for ratiometric sensing applications.

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Section: ■ Experimental Sectionmentioning

confidence: 71%

Section: Resultsmentioning

confidence: 93%

High-Crystallinity Covalent Organic Framework with Dual Fluorescence Emissions and Its Ratiometric Sensing Application

Qian

Dai

Yang

et al. 2017

ACS Appl. Mater. Interfaces

248

146

View full text Add to dashboard Cite

show abstract

“…3a), which was attributed to the ICT from phenanthroline to the guanidium moiety. ICT fluorescent probes involve an overall charge distribution throughout the network and show a significant change in fluorescence upon binding with analytes 67 .…”

Section: Resultsmentioning

confidence: 99%

Fluorescence turn on amine detection in a cationic covalent organic framework

et al. 2022

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Ionic covalent organic frameworks (iCOFs) are new examples of porous materials and have shown great potential for various applications. When functionalized with suitable emission sites, guest uptake via the ionic moieties of iCOFs can cause a significant change in luminescence, making them excellent candidates for chemosensors. In here, we present a luminescence sensor in the form of an ionic covalent organic framework (TGH+•PD) composed of guanidinium and phenanthroline moieties for the detection of ammonia and primary aliphatic amines. TGH+•PD exhibits strong emission enhancement in the presence of selective primary amines due to the suppression of intramolecular charge transfer (ICT) with an ultra-low detection limit of 1.2 × 10‒7 M for ammonia. The presence of ionic moieties makes TGH+•PD highly dispersible in water, while deprotonation of the guanidinium moiety by amines restricts its ICT process and signals their presence by enhanced fluorescence emission. The presence of ordered pore walls introduces size selectivity among analyte molecules, and the iCOF has been successfully used to monitor meat products that release biogenic amine vapors upon decomposition due to improper storage.

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“…Similar ICT probes are known to exhibit changes in fluorescence upon binding with analytes. 128 This fluorescence effect, combined with the Lewis acidity of TGH + ·PD made this system highly attractive for applications in amine sensing. Initial tests with a dispersion of TGH + ·PD in water found a detection limit of 1.2 × 10 −7 M for ammonia, comparable to other high sensitivity chemosensors.…”

Section: Fluorescent Sensorsmentioning

confidence: 99%

Biogenic amine sensors using organic π-conjugated materials as active sensing components and their commercialization potential

Grant¹,

Wolfe²,

Harding³

et al. 2023

J. Mater. Chem. C

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Interaction of water with a benzimidazole derivative: fluorescence and colorimetric recognition of trace level water involving intra‐molecular charge transfer process

Cited by 11 publications

References 44 publications

High-Crystallinity Covalent Organic Framework with Dual Fluorescence Emissions and Its Ratiometric Sensing Application

High-Crystallinity Covalent Organic Framework with Dual Fluorescence Emissions and Its Ratiometric Sensing Application

Fluorescence turn on amine detection in a cationic covalent organic framework

Biogenic amine sensors using organic π-conjugated materials as active sensing components and their commercialization potential

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