Spontaneous optical response towards cyanide ion in water by a reactive binding site probe

Park, Jong Ho; Manivannan, Ramalingam; Jayasudha, Palanisamy; Son, Young‐A

doi:10.1016/j.saa.2020.118190

Cited by 21 publications

(5 citation statements)

References 31 publications

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“…Importantly, the electropositive potential of the C�C unit (indicated by the blue arrow) in F1, as evinced from electrostatic potential (ESP) mapping (Figure 1d), would furnish a Michael-type nucleophilic reaction upon excavating an anionic species that might exhibit a fluorescence "turn-on" response for a definite nucleophilic anion by obstructing the charge transfer from π-rich pyrene. 3,24 Also, the required electronegativity of pyrene and 4-fluorophenyl moieties in F1 (indicated by red arrows) might be conducive for the charge transfer assisted fluorescence "turn-off" response via electrostatic interaction with particular electron-deficient NAs. 25 Investigation of AIEE Characteristics.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Correspondingly, the angle of slippage [(vi) in Figure c] in the dimeric structure was found to be 32.30°, which supports J-aggregation. , Henceforth, J-aggregation and RIR would reverse the typical ACQ behavior of native pyrene and instigate AIEE/GIEE behavior from the aggregated F1 in binary solvent mixture and gel state. Importantly, the electropositive potential of the CC unit (indicated by the blue arrow) in F1, as evinced from electrostatic potential (ESP) mapping (Figure d), would furnish a Michael-type nucleophilic reaction upon excavating an anionic species that might exhibit a fluorescence “turn-on” response for a definite nucleophilic anion by obstructing the charge transfer from π-rich pyrene. , Also, the required electronegativity of pyrene and 4-fluorophenyl moieties in F1 (indicated by red arrows) might be conducive for the charge transfer assisted fluorescence “turn-off” response via electrostatic interaction with particular electron-deficient NAs …”

Section: Resultsmentioning

confidence: 99%

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A Gelation-Induced Enhanced Emission Active Stimuli Responsive and Superhydrophobic Organogelator: “Turn-On” Fluorogenic Detection of Cyanide and Dual-Channel Sensing of Nitroexplosives on Multiple Platforms

et al. 2023

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A pyrene-based highly emissive low-molecular-weight organogelator, [2-(4-fluorophenyl)-3-(pyren-1-yl)acrylonitrile] (F1), is presented, which divulges thixotropic and thermochromic fluorescence switching via reversible gel-to-sol transition and tremendous superhydrophobicity (mean contact angles: 149–160°), devoid of any gelling and/or hydrophobic units. The rationale for the design strategy reveals that the restricted intramolecular rotation (RIR) in J-type self-assembly promotes F1 for the prolific effects of aggregation- and gelation-induced enhanced emission (AIEE and GIEE). Meanwhile, hindrance in charge transfer via the nucleophilic reaction of cyanide (CN–) on the CC unit in F1 facilitates the selective fluorescence “turn-on” response in both solution [9:1 (v/v) DMSO/water] and solid state [paper kits] with significantly lower detection limits (DLs) of 37.23 nM and 13.4 pg/cm2, respectively. Subsequently, F1 discloses CN– modulated colorimetric and fluorescence “turn-off” dual-channel response for aqueous 2,4,6-trinitrophenol (PA) and 2,4-dinitrophenol (DNP) in both solution (DL = 49.98 and 44.1 nM) and solid state (DL = 114.5 and 92.05 fg/cm2). Furthermore, the fluorescent nanoaggregates of F1 in water and its xerogel films permit a rapid dual-channel “on-site” detection of PA and DNP, where the DLs ranged from nanomolar (nM) to sub-femtogram (fg) levels. Mechanistic insights reveal that the ground-state electron transfer from the fluorescent [F1-CN] ensemble to the analytes is responsible for anion driven sensory response, whereas the unusual inner filter effect (IFE) driven photoinduced electron transfer (PET) was responsible for self-assembled F1 response toward desired analytes. Additionally, the nanoaggregates and xerogel films also detect PA and DNP in their vapor phase with reasonable percentage of recovery from the soil and river water samples. Therefore, the elegant multifunctionality from a single luminogenic framework allows F1 to provide a smart pathway for achieving environmentally benign real-world applications on multiple platforms.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

A Gelation-Induced Enhanced Emission Active Stimuli Responsive and Superhydrophobic Organogelator: “Turn-On” Fluorogenic Detection of Cyanide and Dual-Channel Sensing of Nitroexplosives on Multiple Platforms

et al. 2023

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“…In view of the previously reported procedure [26], the sensing mechanism occurring after interaction of cyanide with indole-based molecules is a nucleophilic addition reaction. The cyanide nucleophile attacks the carbon atom of indolium moiety (C=N group) declining its electron -withdrawing ability, hence a change in photophysical properties is observed.…”

Section: Sensing Mechanismmentioning

confidence: 99%

A Novel Fluorescent Probe for the Detection of Cyanide Ions in Solutions and Studies on Its Biophysical Interactions with ctDNA and Proteases

et al. 2022

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A new cationic indolium based styryl dye as a fluorescent probe, (E)-2-(4-(dibutylamino)styryl)-1,3,3trimethyl-3H-indol-1-ium iodide (Ci), was synthesized and its anions selectivity/sensitivity properties /molecular interactions with protease enzymes (pepsin/trypsin) and ctDNA has been studied by spectroscopic and computational methods. The fluorescence measurements at different temperatures indicated that quenching mechanism of enzymes by Ci was static. H and S data pointed out electrostatic/hydrophobic interactions with pepsin, and also hydrogen bonds/van der Waals forces with trypsin of Ci. According to Förster's non-radiative energy transfer, binding distances (r) were calculated as 3.53/3.27 nm for pepsin/trypsin. It was also investigated that groove binding is effective in interaction with ctDNA. The results were supported with molecular docking analyzes which have same tendency. Ci has been demonstrated hypsochromic effect with a decrease in solvent polarity and it showed highly selective colorimetric and fluorometric sensing behavior for cyanide ions in organic solvent and aqueous solution. 1 H NMR titration was performed to examine the interaction mechanism between Ci and cyanide ions. The LOD values of cyanide ion were reported as 4.87x10 -9 M and 9.70x10 -7 M in DMSO and DMSO/H2O binary mixture, respectively. In addition, sensitivity of Ci as a chemosensor to cyanide ions was investigated in bitter almond samples.

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“…27 Phenothiazines emit fluorescence and have properties as electron-donating groups, [28][29][30][31] while many studies have reported the reaction of the indolium cation, which is a strong electron-withdrawing group, with CN − . [32][33][34][35][36][37][38][39][40][41][42][43][44] Therefore, we thought that a phenothiazine/indolium compound could also be applied for the CN − detection. We synthesized a novel phenothiazine/indolium conjugated molecule (PI) as a CN − sensing dye; its color and fluorescence changes in response to CN − , as well as the selectivity to the target analyte, were also investigated.…”

Section: Introductionmentioning

confidence: 99%

A novel turn-on fluorescent sensor for cyanide ions based on the charge transfer transition of phenothiazine/indolium compounds

et al. 2021

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Spontaneous optical response towards cyanide ion in water by a reactive binding site probe

Cited by 21 publications

References 31 publications

A Gelation-Induced Enhanced Emission Active Stimuli Responsive and Superhydrophobic Organogelator: “Turn-On” Fluorogenic Detection of Cyanide and Dual-Channel Sensing of Nitroexplosives on Multiple Platforms

A Gelation-Induced Enhanced Emission Active Stimuli Responsive and Superhydrophobic Organogelator: “Turn-On” Fluorogenic Detection of Cyanide and Dual-Channel Sensing of Nitroexplosives on Multiple Platforms

A Novel Fluorescent Probe for the Detection of Cyanide Ions in Solutions and Studies on Its Biophysical Interactions with ctDNA and Proteases

A novel turn-on fluorescent sensor for cyanide ions based on the charge transfer transition of phenothiazine/indolium compounds

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