Quinoline-based chemosensor for fluoride and acetate: A combined experimental and DFT study

Yadav, Urmiladevi Narad; Pant, Preeti L.; Sharma, Darshana; Sahoo, Suban K.; Shankarling, Ganapati S.

doi:10.1016/j.snb.2014.02.075

Cited by 47 publications

(22 citation statements)

References 51 publications

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“…The probes (receptors) are generally known to interact with analytes (anions) either via covalent binding, involving addition 22 or substitution type reactions 23,24 , or via non-covalent interactions that involve formation of host-guest type complexes. [25][26][27] A recent study with quinoline based probe has described the deprotonation mechanism with fluoride and acetate anions to induce changes in observed absorption/fluorescence pattern.…”

Section: Resultsmentioning

confidence: 99%

“…[25][26][27] A recent study with quinoline based probe has described the deprotonation mechanism with fluoride and acetate anions to induce changes in observed absorption/fluorescence pattern. 24 Another anion sensing study with 9alkoxy acridinium has demonstrated the nucleophilic addition of anions (F -/AcO¯) at C9 position of acridinium ring causing de-aromatization, consequently inducing drastic changes in absorption/fluorescence signals of acridinium moiety. 22 Our studies with quinoxalinium salts 1-5 revealed dual mode of action, that is; 1) via nucleophilic addition of small anions (F¯/AcO¯), and 2) via host-guest type complex formation with larger anion (ascorbate).…”

Section: Resultsmentioning

confidence: 99%

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Novel quinoxaline based chemosensors with selective dual mode of action: nucleophilic addition and host–guest type complex formation

et al. 2016

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§ Shared first author(contributed equally) * AbstractNew quinoxalinium salts 1-5 as chemosensors have been exploited via naked eye, UV-Vis absorption, fluorescence quenching and 1 H NMR experiments. New sensors 1-5 showed dual mode, nucleophilic addition and host-guest type complex towards anion (F¯, AcO¯ and ascorbate) detection. Small anions (F¯/AcO¯) showed nucleophilic addition at C2 position of quinoxalinium cation, while larger anion (ascorbate), revealed the formation of host-guest type complex due to steric hindrance posed by C3 of phenyl ring. Nucleophilic addition of small anions (F¯/AcO¯) leads to de-aromatization of quinoxalinium cation. However in the case of larger anion, ascorbate, host-guest type complex formation induces changes in absorption/fluorescence signals of quinoxalinium moiety. This selective binding has been confirmed on the basis of 1 H NMR spectroscopic technique, whereupon nucleophilic addition of small anions (F¯/AcO¯) was confirmed by monitoring characteristic proton NMR signals of H a and methylene protons (CH 2 ), which were clearly shifted in case of fluoride and acetate ions addition confirming de-aromatization and nucleophilic addition. Whereas no such peak shifting was observed in case of ascorbate ion addition confirming non-covalent addition of ascorbate.Theoretical insight into the selectivity and complexation behavior of ascorbate ion with quinoxaline moiety is gained through density functional theory (DFT) calculations. Moreover, the absorption properties of these complexes are modeled theoretically, and compared with the experimental data. In addition, thermal decomposition of sensor (1 and 2) has been studied by the means of differential scanning calorimetry (DSC), thermogravimetry (TG), and differential thermogravimetry (DTG) to signify their utility at variable temperature.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Novel quinoxaline based chemosensors with selective dual mode of action: nucleophilic addition and host–guest type complex formation

et al. 2016

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“…For real sample analysis, we carried out the qualitative detection of F À ions in commercially available toothpaste. The test solutions for this experiment were prepared by adopting recently reported method [32]. The toothpaste sample solution was prepared as 100 mg/mL in water.…”

Section: Analytical Applicationmentioning

confidence: 99%

Substituent effects on anion sensing of salicylidene Schiff base derivatives: Tuning sensitivity and selectivity

Zang

Jiang

2015

Spectrochimica Acta Part A: Molecular and Biomolecular Spectros

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“…Colorimetric signaling like a direct naked-eye detectable color changing provides an easy to use sensor with high sensitivity and selectivity [1][2][3]. Most of the sensor-anion interactions are based on hydrogen bonding interaction and some of them are followed by sensor deprotonation [4][5][6]. Furthermore, the chemosensor sensing mechanisms have been suggested as intramolecular charge transfer (ICT) [7], photoinduced electron transfer (PET) [8], excited states proton transfer (ESPT) [9], and metal-ligand charge transfer (MLCT) [10].…”

Section: Introductionmentioning

confidence: 99%

Chalcone Based Colorimetric Sensor for Anions: Experimental and TD-DFT Study

Fitriana¹,

Pranowo²,

Purwono³

2018

Indones. J. Chem.

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Quinoline-based chemosensor for fluoride and acetate: A combined experimental and DFT study

Cited by 47 publications

References 51 publications

Novel quinoxaline based chemosensors with selective dual mode of action: nucleophilic addition and host–guest type complex formation

Novel quinoxaline based chemosensors with selective dual mode of action: nucleophilic addition and host–guest type complex formation

Substituent effects on anion sensing of salicylidene Schiff base derivatives: Tuning sensitivity and selectivity

Chalcone Based Colorimetric Sensor for Anions: Experimental and TD-DFT Study

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