Electrochemical behavior of some triazine derivatives at glassy carbon electrode in non-aqueous media

Farzinnejad, N.; Beigi, Ali Akbar Miran; Fotouhi, Lida; Torkestani, K.; Ghadirian, Hossein Ali

doi:10.1016/j.jelechem.2005.03.032

Cited by 8 publications

(4 citation statements)

References 38 publications

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“…3a, the CV of compound 2 has a reduction peak at −1.64 V, without any cathodic peak at reverse scan, indicating that the peak is electron transfer processes having irreversible nature. The cathodic peak can be attributed to electrochemical cleavage of -bonding in triazine ring [31]. On the other hand, at the anodic side, the CV showed very weak wave near the limit of anodic range, but the nature of the peak could not be satisfactorily evaluated by analyzing the cyclic voltammetric data.…”

Section: Resultsmentioning

confidence: 95%

Synthesis of novel tripodal-benzimidazole from 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine: Structural, electrochemical and antimicrobial studies

Koç

Bingöl

Saf

et al. 2010

Journal of Hazardous Materials

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Section: Resultsmentioning

confidence: 95%

Synthesis of novel tripodal-benzimidazole from 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine: Structural, electrochemical and antimicrobial studies

Koç

Bingöl

Saf

et al. 2010

Journal of Hazardous Materials

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“…The triazine ring system does not display reversible oxidationreduction characteristics. 10,11 X-ray quality crystals of 4 and 6 were grown from dichloroethane. The structure of 4 is displayed in Figure 4.…”

Section: Letter Syn Lettmentioning

confidence: 99%

Pentaerythritol Trinitrate Substituted s-Tetrazine and s-Triazine

Chávez

Myers

Veauthier

et al. 2015

Synlett

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The synthesis of pentaerythritol trinitrate persubstituted 1,2,4,5-tetrazine and 1,3,5-triazine is reported. These materials were characterized with respect to their chemical and energetic materials properties. X-ray crystallographic analyses were also performed. The UV/Vis, Raman, and cyclic voltammetry data were collected and are reported.Recently, we described the syntheses of nitrate ester substituted derivatives of chloro-1,2,4,5-tetrazines. 1 These materials were synthesized in order to study their electroactive behavior, and we discovered that these materials formed stable radical anions when subjected to cyclic voltammetry experiments. 2 We also found that the corresponding radical anions could be formed reversibly. We have now focused our efforts on placing nitrate ester containing substituents on both the 3-and 6-position of the 1,2,4,5-tetrazine ring system for the following reasons: 1. to increase the energy content of the resultant product and, 2. to compare the electrochemical behavior of the symmetrical and unsymmetrical tetrazine ring systems.At the same time, we were interested in studying similar systems based upon the 1,3,5-triazine heterocycle. While there are numerous examples of electrochemical studies of metal complexes of 1,3,5-triazine derivatives 3 there are fewer studies of neutral 1,3,5-triazine compounds 4 and no studies of energetic 1,3,5 triazine systems. For this heterocyclic system, we chose to attach nitrate ester substituted moieties at the 2-, 4-, and 6-position.We pursued the use of pentaerythritol trinitrate (PETRIN, 1) 5 as the nitrate ester substituent to attach to the heterocyclic ring systems through nucleophilic substitution through the alcohol functional group. In the case of the 1,2,4,5-tetrazine system, 3,6-dichlorotetrazine (2) was chosen as the electrophile. In our initial studies 1 we found that the reaction of one equivalent each of 1 and 2 in the presence of 2,4,6-collidine led to monosubstitution (3). The addition of two equivalents of 1 under the same reaction conditions did not lead to the desired product 4, but only compound 3, even under forcing conditions. In our prior studies we have observed reduction in reactivity of the remaining chloro substituent when a strongly electron-donating substituent is present. We found that the reaction could be performed in neat 2,4,6-collidine, but the yields were very poor. Ultimately, the reaction was found to proceed in a two-step process by first preparing 3, followed by treatment with an additional equivalent of 1 in the presence of 4-dimethylaminopyridine (DMAP, Scheme 1). 6,7 The reaction can be performed with DMAP in a one-step process from 1 and 2, but the yield is very poor.In our studies of the triazine system, we chose cyanuric chloride (5) as the electrophile. In this case, the use of three equivalents of 1 in the presence of neat 2,4,6-collidine also lead to the desired product 6 in reasonable yield. Interestingly, we found that this reaction could not be performed using DMAP as the base and dichloromethane a...

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“…Chronoamperometry (CA) is an important method for the characterization of the EC mechanism and also for the determination of the rate constant of follow-up chemical reactions [34]. Therefore, this method was applied in this study and again employed for the determination of the diffusion coefficient.…”

Section: Double Potential Step Chronoamperometrymentioning

confidence: 99%

Electrochemical response of the two isomers conjugated acids, maleic and fumaric, on glassy carbon electrode modified with platinum nanoparticles

et al. 2009

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Cyclic voltammetry (CV), electrochemical impedance spectroscopy (EIS), and chronoamperometry (CA) techniques are essentially used for the study of the electroreduction of the two isomers maleic and fumaric acid systems in 0.1 M KCl at 298 K. The measurements are carried out on Pt nanoparticles electrodeposited on glassy carbon electrode (GCE). The modification of the electrode enables the appearance of better resolved peaks of the cyclic voltammograms of the two isomers of the acids in comparison with the poor behavior in absence of the modification. Two well-separated reversible cathodic waves at -0.44 and -0.59 V versus Ag/AgCl are characterizing the electroreduction cyclic voltammogram of maleic acid. The electroreduction of fumaric acid shows only one reversible peak at -0.362 V versus Ag/AgCl is observed. Peak separations and current functions together with other parameters of the electrochemical behavior of both isomers are calculated and discussed. Rate parameters of the anion radicals of both isomers in 0.1 M KCl on immobilized GCE with Pt nanoparticles are obtained and discussed.

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Electrochemical behavior of some triazine derivatives at glassy carbon electrode in non-aqueous media

Cited by 8 publications

References 38 publications

Synthesis of novel tripodal-benzimidazole from 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine: Structural, electrochemical and antimicrobial studies

Synthesis of novel tripodal-benzimidazole from 2,4,6-tris(p-formylphenoxy)-1,3,5-triazine: Structural, electrochemical and antimicrobial studies

Pentaerythritol Trinitrate Substituted s-Tetrazine and s-Triazine

Electrochemical response of the two isomers conjugated acids, maleic and fumaric, on glassy carbon electrode modified with platinum nanoparticles

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