An imidazole based colorimetric sensor for fluoride anion

A one‐pot, two‐step, simple, efficient and eco‐friendly oxidation of internal alkynes as a key step towards the synthesis of 2,4,5‐trisubstituted imidazoles, using an inexpensive I2/DMSO system, has been reported. This metal and acid‐free synthesis proceeded smoothly to furnish a variety of synthetically useful trisubstituted imidazoles in moderate to excellent yields. In an effort to demonstrate the potential future applications of this system, a double oxidation study was undertaken and the desired trisubstituted imidazoles obtained in good to moderate yields.

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“…2‐(2‐Nitrophenyl)‐4,5‐diphenyl‐1 H ‐imidazole (3f): Yield 107.53 mg (63 %); yellow solid; m.p. 268–272 °C.…”

Section: Methodsmentioning

confidence: 99%

One‐Pot, Two‐Step Metal and Acid‐Free Synthesis of Trisubstituted Imidazole Derivatives via Oxidation of Internal Alkynes Using an Iodine/DMSO System

Naidoo

Jeena

2018

Eur J Org Chem

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“…This is attributed to the fact that such strategies hold the potential to overcome the requirement of bulky and sophisticated instrumentation, tedious and sample preconcentration, delayed signal readout, and high detection limits [4][5][6]. The most common and easiest molecular receptor design for sensing anions like fluoride (F − ), cyanide (CN − ), and acetate (CH 3 COO − ) involve polarization of N-H bond in a range of functionalities like amides, ureas, thioureas, ammonium, imidazole and in imidazolium compounds [7][8][9][10][11][12]. Such systems are well established to detect the anions through hydrogen bonding and/or proton transfer (PT) mechanism in polar aprotic solvents [13,14].…”

Section: Introductionmentioning

confidence: 99%

DFT and TD-DFT Study of Only First Diaminomalenonitrile Based Molecular Receptor for Fluoride Anion: Correlation of Calculated and Experimental Results

et al. 2021

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In this work, the sensing mechanism of a novel anion receptor, 2-amino-((E)-(4-cyanobenzalidine) amino) maleonitrile reported by Sankar et al. (Analyst 138:4760-4763, 2013) was investigated theoretically with the help of density functional theory (DFT) and time-dependent density functional theory (TD-DFT). From the frontier molecular orbital analysis, it is reasonable to support the proposed charge transfer (ICT) enhancement in the receptor molecule in the presence of F−. A significant reduction in the energy gap (ΔE) from 4.014 eV to 2.342eV between highest occupied and lowest unoccupied energy levels was revealed, leading to the strong redshift of its absorption characteristics. Moreover, 1H NMR was also calculated to further understand the mechanistic insights by using the gauge independent atomic orbital (GIAO) method with B3LYP methods and the 6-311++G (d,p) basis set. The spectra were simulated, and the chemical shifts linked to TMS were compared with experimental. Besides, Intrinsic Reaction Coordinates (IRC) were also calculated to understand the sensing mechanism.

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“…anticancer, antimicrobial, anti‐inflammatory, anticonvulsant, antidiabetic, antihypertensive, antitubercular, antiviral and antiparasitic reagents, antioxidants, proton pump inhibitors, anticoagulants, hormone modulators, CNS stimulants as well as depressants and lipid level modulators, etc . Within the imidazole ring, the protonated nitrogen atom (–C–NH–) is a good source for hydrogen bonding interaction either with a variety of therapeutic targets, exhibiting broad pharmacological activities or with a variety of toxic anions like cyanide, fluoride, giving high detection activity as anion chemo‐sensor , …”

Section: Introductionmentioning

confidence: 99%

“…[13] Within the imidazole ring, the protonated nitrogen atom (-C-NH-) is a good source for hydrogen bonding interaction [14] either with a variety of therapeutic targets, exhibiting broad pharmacological activities [15] or with a variety of toxic anions like cyanide, fluoride, giving high detection activity as anion chemo-sensor. [16,17] On one hand the de-protonated nitrogen atom (-C=N-) is a good resource for coordination with metal ions forming a series of imidazole-based chelates, which have considerable attention in coordination chemistry, not only due to their well-documented biological activities, but also they are efficient and recyclable catalysts for the reaction of various epoxides with CO 2 to selectively yield cyclic carbonates, [18] hydroxylation of benzene to phenol, [19] epoxidation of olefins, [20] and in corrosion inhibition. [21] Imidazoles are remarkably effective compounds both with respect to their inhibition activity and favorable selectivity.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Characterization, Modeling, and Antimicrobial Activity of Fe^III, Co^II, Ni^II, Cu^II, and Zn^II Complexes Based on Tri‐substituted Imidazole Ligand

Ismael

Abdou

Abdel‐Mawgoud

2018

Zeitschrift anorg allge chemie

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The reaction of the synthesized 2‐(4,5‐diphenyl‐1H‐imidazol‐2‐yl) phenol, (HL) ligand with FeIII, CoII, NiII, CuII, and ZnII ions at room temperature resulted in the formation of the five complexes; [Fe(L)2(H2O)(Cl)]·2H2O and [M(L)2)]·nH2O [M = Co, Zn (n = 2), Ni, Cu (n = 1)]. The ligand and its complexes were characterized based on elemental analyses, spectral, magnetic and molar conductance measurements. The molecular and electronic structure of the ligand and its complexes was optimized theoretically and the quantum chemical parameters were calculated. The results revealed an interesting geometrical variation; octahedral for FeL, seesaw for CoL, distorted square planar for NiL and CuL, as well a tetrahedral arrangement for ZnL. The HL ligand and its metal complexes were screened against the growth of pathogenic bacteria [Escherichia coli (G–) and Bacillus cereus (G+)] and fungi (Aspergillus fumigatus) in terms of the minimum inhibitory concentration (MIC). The metal complexes showed high enhancement as antimicrobial candidates with lower MIC values compared with their parent ligand. Structure activity relationship formula was quantified by correlating the experimental MIC values with theoretical electronic chemical properties. Molecular docking of the complexes against CYP51B protein of A. fumigatus, the target enzyme for the antimicrobial reagents, was achieved to find the best orientation of the substrate, which would form a stable complex with overall minimum energy. The docking results enhanced the activity of the imidazole‐based complexes as promising antimicrobial candidates.

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An imidazole based colorimetric sensor for fluoride anion

Cited by 18 publications

References 46 publications

One‐Pot, Two‐Step Metal and Acid‐Free Synthesis of Trisubstituted Imidazole Derivatives via Oxidation of Internal Alkynes Using an Iodine/DMSO System

One‐Pot, Two‐Step Metal and Acid‐Free Synthesis of Trisubstituted Imidazole Derivatives via Oxidation of Internal Alkynes Using an Iodine/DMSO System

DFT and TD-DFT Study of Only First Diaminomalenonitrile Based Molecular Receptor for Fluoride Anion: Correlation of Calculated and Experimental Results

Synthesis, Characterization, Modeling, and Antimicrobial Activity of Fe^III, Co^II, Ni^II, Cu^II, and Zn^II Complexes Based on Tri‐substituted Imidazole Ligand

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An imidazole based colorimetric sensor for fluoride anion

Cited by 18 publications

References 46 publications

One‐Pot, Two‐Step Metal and Acid‐Free Synthesis of Trisubstituted Imidazole Derivatives via Oxidation of Internal Alkynes Using an Iodine/DMSO System

One‐Pot, Two‐Step Metal and Acid‐Free Synthesis of Trisubstituted Imidazole Derivatives via Oxidation of Internal Alkynes Using an Iodine/DMSO System

DFT and TD-DFT Study of Only First Diaminomalenonitrile Based Molecular Receptor for Fluoride Anion: Correlation of Calculated and Experimental Results

Synthesis, Characterization, Modeling, and Antimicrobial Activity of FeIII, CoII, NiII, CuII, and ZnII Complexes Based on Tri‐substituted Imidazole Ligand

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Synthesis, Characterization, Modeling, and Antimicrobial Activity of Fe^III, Co^II, Ni^II, Cu^II, and Zn^II Complexes Based on Tri‐substituted Imidazole Ligand