New insight into the electrochemical reduction of different aryldiazonium salts in aqueous solutions

Tavakkoli, Zahra; Goljani, Hamed; Sepehrmansourie, Hassan; Nematollahi, Davood; Zolfigol, Mohammad Ali

doi:10.1039/d1ra04482f

Cited by 12 publications

(9 citation statements)

References 53 publications

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“…When the film thickness was plotted as a function of the Hammett constants 47 σ para and σ meta , there was no correlation. It should be remembered that the reduction potentials of diazonium salts can be correlated with Hammett constants as shown by the recent work by Tavakkoli et al; 15 however, such a correlation cannot be observed in this much more complex process.…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…Schematic of diazonium cations used in this work and a sample of the extensive catalogue of diazonium cations for surface modification (in the absence of monomers) present in the literature. ,,,− Note: All anions in this work are tetrafluoroborate (BF 4 – ), but an array of anions is used in the literature (right column).…”

Section: Introductionmentioning

confidence: 93%

“…The irreversible reduction of aryldiazonium salts has provided a reliable method to modify surfaces (graphite, metals, carbon fiber), facilitated by chemical or electrochemical reduction, for nearly 30 years . Demonstrated as a very useful technique, its versatility has been proven through applications in industries such as the biomedical and carbon fiber industries. − The diversity of functional groups (e.g., NO 2 , NH 2 , COOH, , alkynes, and many others − ) able to be installed onto a surface via an aryl ring anchoring moiety is considerable. − …”

Section: Introductionmentioning

confidence: 99%

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Examining the Role of Aryldiazonium Salts in Surface Electroinitiated Polymerization

et al. 2022

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Historically, the irreversible reduction of aryldiazonium salts has provided a reliable method to modify surfaces, demonstrating a catalogue of suitable diazonium salts for targeted applications. This work expands the knowledge of diazonium salt chemistry to participate in surface electroinitiated emulsion polymerization (SEEP). The influence of concentration, electronic effects, and steric hindrance/regiochemistry of the diazonium salt initiator on the production of polymeric films is examined. The objective of this work is to determine if a polymer film can be tailored, controlling the thickness, density, and surface homogeneity using specific diazonium chemistry. The data presented herein demonstrate a significant difference in polymer films that can be achieved when selecting a variety of diazonium salts and vinylic monomers. A clear trend aligns with the electron-rich diazonium salt substitution providing the thickest films (up to 70.9 ± 17.8 nm) with increasing diazonium concentration and electron-withdrawing substitution achieving optimal homogeneity for the surface of the film at a 5 mM diazonium concentration.

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Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 93%

Section: Introductionmentioning

confidence: 99%

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Examining the Role of Aryldiazonium Salts in Surface Electroinitiated Polymerization

et al. 2022

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“…These E ox S1 values are more negative than the reduction potential of p-chlorobenzene diazonium salt. 13 From these results, we estimated that both 2 and 2 À are the photoactive forms of BEY in this reaction (Scheme S3, ESI †). Arylation was performed for various aryldiazonium salts with 631 nm LED irradiation (Scheme 1).…”

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confidence: 91%

Bridged eosin Y: a visible and near-infrared photoredox catalyst

et al. 2022

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“…Among numerous functionalization strategies, the electrochemical reduction of diazonium salts [ 30 , 31 , 32 , 33 , 34 ] has been proposed as a versatile method that affords the grafting of a large variety of molecules at conductive substrates [ 35 , 36 ]. So far it has been applied for different types of carbon-based substrates such as glassy carbon [ 37 ], screen-printed carbon [ 38 ], carbon paste [ 39 ], graphite pencil [ 40 ] or carbon nanomaterials electrodes [ 41 , 42 ], that function as transducers in a large number of sensors for bioanalytes, such as proteins [ 43 ], DNA [ 44 ], RNA or cells [ 45 ]. Although great effort has been dedicated to this subject, there is still no refined method available to mass-produce highly stable, efficient biosensors with real applicability in biomedicine.…”

Section: Introductionmentioning

confidence: 99%

Electrochemical Detection Platform Based on RGO Functionalized with Diazonium Salt for DNA Hybridization

2022

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In this paper, we propose an improved electrochemical platform based on graphene for the detection of DNA hybridization. Commercial screen-printed carbon electrodes (SPCEs) were used for this purpose due to their ease of functionalization and miniaturization opportunities. SPCEs were modified with reduced graphene oxide (RGO), offering a suitable surface for further functionalization. Therefore, aryl-carboxyl groups were integrated onto RGO-modified electrodes by electrochemical reduction of the corresponding diazonium salt to provide enough reaction sites for the covalent immobilization of amino-modified DNA probes. Our final goal was to determine the optimum conditions needed to fabricate a simple, label-free RGO-based electrochemical platform to detect the hybridization between two complementary single-stranded DNA molecules. Each modification step in the fabrication process was monitored by cyclic voltammetry (CV) and electrochemical impedance spectroscopy (EIS) using [Fe(CN)6]3−/4− as a redox reporter. Although, the diazonium electrografted layer displayed the expected blocking effect of the charge transfer, the next steps in the modification procedure resulted in enhanced electron transfer properties of the electrode interface. We suggest that the improvement in the charge transfer after the DNA hybridization process could be exploited as a prospective sensing feature. The morphological and structural characterization of the modified electrodes performed by scanning electron microscopy (SEM) and Raman spectroscopy, respectively, were used to validate different modification steps in the platform fabrication process.

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New insight into the electrochemical reduction of different aryldiazonium salts in aqueous solutions

Abstract: Electrochemical reduction of different aryldiazonium salts in aqueous solution was studied. It is shown that the aryldiazonium salts are converted to the corresponding aryl radical and aryl anion.

Cited by 12 publications

References 53 publications

Examining the Role of Aryldiazonium Salts in Surface Electroinitiated Polymerization

Examining the Role of Aryldiazonium Salts in Surface Electroinitiated Polymerization

Bridged eosin Y: a visible and near-infrared photoredox catalyst

Electrochemical Detection Platform Based on RGO Functionalized with Diazonium Salt for DNA Hybridization

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