Fluoroaromatic 2H-imidazole-based push-pull fluorophores: Synthesis, theoretical studies, and application opportunities as probes for sensing the pH in saliva

Moseev, Timofey D.; Вараксин, Михаил В.; Virlova, Elizaveta A.; Medvedeva, M. V.; Свалова, Т. С.; Melekhin, Vsevolod V.; Tsmokaluk, Anton N.; Козицина, А. Н.; Чарушин, В. Н.; Чупахин, О. Н.

doi:10.1016/j.dyepig.2022.110251

Cited by 8 publications

(8 citation statements)

References 50 publications

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“…As shown in Table , calculations establish that the highest E HOMO is observed in compound C2 (−4.949 eV), which may be attributed to the additional inductive effect (electron-donating) of lateral methyl groups. Inhibitors with a high E HOMO can remarkably push electrons into the low vacancy orbital of the corrosive environment, thereby delaying the anodic processes. − In addition, the stability of LUMO supports the electron-receiving potential of the corrosion inhibitor, facilitating the interaction between them. This reaction improves the isolation of the corrosive material from the corrosive environment.…”

Section: Resultsmentioning

confidence: 99%

Corrosion Inhibition of Azo Compounds Derived from Schiff Bases on Mild Steel (XC70) in (HCl, 1 M DMSO) Medium: An Experimental and Theoretical Study

Zobeidi,

Neghmouche Nacer,

Atia

et al. 2023

ACS Omega

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The inhibitory activity of three prepared azo compounds derived from Schiff bases, namely, bis[5-(phenylazo)-2-hydroxybenzaldehyde]-4,4′-diaminophenylmethane (C1), bis[5-(4-methylphenylazo)-2-hydroxybenzaldehyde]-4,4′-diaminophenylmethane (C2), and bis[5-(4-bromophenylazo)-2-hydroxybenzaldehyde]-4,4′-diaminophenylmethane (C3), against corrosion of steel type XC70 in (HCl, 1 M DMSO) medium was investigated experimentally by electrochemical measurements and theoretically using density functional theory (DFT). The correlation between corrosion inhibition and concentration is direct. The maximum inhibition efficiency at 6 × 10–5 M for the three azo compounds derived from Schiff bases was 64.37, 87.27, and 55.47% for C1, C2, and C3, respectively. The Tafel curves indicate that the inhibitors follow a mixed but predominantly anodic inhibitor system and have a Langmuir isothermal adsorption process. The observed inhibitory behavior of compounds was supported by DFT calculation. It was also found that there was a strong correspondence between the theoretical and experimental results.

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Section: Resultsmentioning

confidence: 99%

Corrosion Inhibition of Azo Compounds Derived from Schiff Bases on Mild Steel (XC70) in (HCl, 1 M DMSO) Medium: An Experimental and Theoretical Study

Zobeidi,

Neghmouche Nacer,

Atia

et al. 2023

ACS Omega

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“…In this review, a comprehensive examination of the applications of PFB-derived molecules in the development of diagnostic and therapeutic materials is discussed. In the case of the diagnostic materials, D-π-A, TICT, ICT, and leaving group cleavage or deprotecting strategies are the most exploited. In developing therapeutic material capabilities of PFBs such as deprotection, high reactivity and ease of polymerization are utilized.…”

Section: Discussionmentioning

confidence: 99%

“…The pentafluorophenyl group (EWG) helped in stabilizing the energy of both the lowest unoccupied molecular orbital (LUMO) and the highest occupied molecular orbital (HOMO). The authors have used human-derived real saliva samples to determine the detection potential of 39 for pH …”

Section: Pfbs As Diagnostic Toolsmentioning

confidence: 99%

“…(d) Current work on the design of 2 H -imidazole-based push–pull fluorophores 27 (BRB/DMSO (99/1% v/v, pH 7)) (refer to the web version of this article to view the legend color). Reproduced from ref with permission from Elsevier.…”

Section: Pfbs As Diagnostic Toolsmentioning

confidence: 99%

“…The authors have used human-derived real saliva samples to determine the detection potential of 39 for pH. 83 In 2022, Kim and co-workers developed a fluorescent molecular probe 41 for the detection of Au(III) ions. Probe 41 possesses a tetraphenylethylene (TPE)-based fluorophore unit and PFB as an electron-deficient unit (Figure 13a).…”

Section: ■ Pfbs As Diagnostic Toolsmentioning

confidence: 99%

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Pentafluorobenzene: Promising Applications in Diagnostics and Therapeutics

Nair,

Seo,

Hong

et al. 2023

ACS Appl. Bio Mater.

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Pentafluorobenzene (PFB) represents a class of aromatic fluorine compounds employed exclusively across a spectrum of chemical and biological applications. PFBs are credited with developing various chemical synthesis techniques, networks and biopolymers, bioactive materials, and targeted drug delivery systems. The first part of this review delves into recent developments in PFB-derived molecules for diagnostic purposes. In the latter segment, PFB's role in the domain of theragnostic applications is discussed. The review elucidates different mechanisms and interaction strategies applied in leveraging PFBs to formulate diagnostic and theragnostic tools, substantiated by proper examples. The utilization of PFBs emerges as an enabler, facilitating manifold reactions, improving materials' properties, and even opening avenues for explorative research.

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Blue‐Emitting 2‐Fluoroaryl‐1,2,3‐Triazole Fluorophores: Synthesis, Theoretical Calculations, and Optical Properties

et al. 2023

Self Cite

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A convenient multistep synthetic methodology to afford prospective push‐pull fluorophores based on the N(2)‐fluoroaryl‐1,2,3‐triazole scaffold as valuable functional blocks in the design of blue‐emitting organic materials is reported. The strategy includes five synthetic steps with yields of 60–99% at each stage. The obtained photoactive molecules, 2‐fluoroaryl‐5‐aryl‐4‐methyl‐1,2,3‐triazoles, were found to possess a blue‐violet emission in the range of λ=330–440 nm and the absolute quantum yield of >99% in solvents of different polarities. The electron transfer mechanistic features in the excited states for the developed N(2)‐fluoroaryl‐1,2,3‐triazoles compared to the 1,2,3‐triazoles‐1‐oxide analogues were also studied by using DFT and CIS calculations.

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Fluoroaromatic 2H-imidazole-based push-pull fluorophores: Synthesis, theoretical studies, and application opportunities as probes for sensing the pH in saliva

Cited by 8 publications

References 50 publications

Corrosion Inhibition of Azo Compounds Derived from Schiff Bases on Mild Steel (XC70) in (HCl, 1 M DMSO) Medium: An Experimental and Theoretical Study

Corrosion Inhibition of Azo Compounds Derived from Schiff Bases on Mild Steel (XC70) in (HCl, 1 M DMSO) Medium: An Experimental and Theoretical Study

Pentafluorobenzene: Promising Applications in Diagnostics and Therapeutics

Blue‐Emitting 2‐Fluoroaryl‐1,2,3‐Triazole Fluorophores: Synthesis, Theoretical Calculations, and Optical Properties

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