The effects of 4,7-di(pyrrolidin-1-yl) substituents on the reduction and oxidation mechanisms of 1,10-phenanthrolines: New perspectives in tailoring of phenantroline derivatives

Wantulok, Jakub; Sokolová, Romana; Degano, Ilaria; Kolivoška, Viliam; Nycz, Jacek E.

doi:10.1016/j.electacta.2020.137674

Cited by 3 publications

(4 citation statements)

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“…The cyclic voltammograms obtained for the reduction of compounds 1 – 4 (Figure 2) show five cathodic waves corresponding to the reduction of 1,10‐phenanthroline moiety in the molecules. Reduction of 1,10‐phenanthroline in solution of 0.1 M TBAPF 6 in acetonitrile is shown in recent article [16] . The spatial distribution of LUMO is shown in Figure S3.…”

Section: Resultsmentioning

confidence: 93%

“…Further oxidation of phenothiazine substituents to their sulfoxide proceeds at 1.70 V (wave II) and 1.78 V (wave II’) (Scheme 2). The oxidation wave III at 1.89 V is attributed to the oxidation of 1,10‐phenanthroline moiety (the oxidation of unsubstituted 1,10‐phenanthroline has the peak potential at 1.90 V) [16] …”

Section: Resultsmentioning

confidence: 99%

“…HPLC‐MS/MS allowed the identification of the sulfoxide (two isomers) and the di(sulfoxide) (see below, part Identification of products). Oxidation of 1,10‐phenanthroline core occurs at the wave III [16] …”

Section: Resultsmentioning

confidence: 99%

“…In this work, inspired by our recent findings in the reduction and oxidation mechanisms of N ‐pyrrolidinyl derivatives of 1,10‐phenanthrolines, [16] we present an innovative idea of substituting 1,10‐phenanthroline by phenothiazine and carbazole (compounds 1 to 4 , see Scheme 1) redox active moieties to create novel ligands for future complexes with transition metal complexes with specific redox and optical properties. Comprehensive electrochemical and spectroelectrochemical analysis of these derivatives is carried out.…”

Section: Introductionmentioning

confidence: 99%

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Spectroelectrochemical Properties of 1,10‐Phenanthroline Substituted by Phenothiazine and Carbazole Redox‐active Units

et al. 2021

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Complexes of 1,10‐phenanthrolines with cations of transition metals have broad range of applications. This work aims at designing and investigating phenothiazine and carbazole substituted 1,10‐phenanthrolines as ligands for future complexes with transient metal cations. The combined electrochemical, spectroelectrochemical and DFT studies were employed to demonstrate the effect of broken symmetry in substituted 4,7‐di(phenothiazine)‐1,10‐phenanthrolines on their spectroelectrochemical properties. A reversible color change (new absorption band around 500 nm) due to phenothiazine radical cation was observed in the first oxidation step. Results further indicate that phenothiazine substituents behave as two equivalent but almost electronically isolated redox centres. The work additionally presents a comprehensive reaction mechanistic study of oxidation and reduction processes complemented by HPLC‐MS/MS identification.

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Section: Resultsmentioning

confidence: 93%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Spectroelectrochemical Properties of 1,10‐Phenanthroline Substituted by Phenothiazine and Carbazole Redox‐active Units

et al. 2021

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Voltammetric study of new psychoactive substance 3‐fluorophenmetrazine

Jiroušková

Čabala

Sokolová

2022

Electrochemical Science Adv

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Electrochemical oxidation of the new psychoactive substance 3‐fluorophenmetrazine (FPM) was studied in phosphate buffers by cyclic voltammetry and differential pulse voltammetry (DPV) on a glassy carbon electrode. The redox potential of FPM in buffered solution strongly depends on pH. Cyclic voltammetry behavior shows the partial influence of adsorption on the electrode process not allowing detailed analysis of the individual steps of the reaction scheme, it means the involvement of electron transfer (E) and chemical reaction (C). Nevertheless, the irreversible shape of the cyclic voltammogram is explained by the participation of hydroxylation nucleophilic addition of water (hydroxylation) after two‐electron/two‐proton oxidation of molecule at the tetrahydro‐1,4‐oxazine ring. The suggested mechanism leading to hydroxylated derivative 2‐(3‐fluorophenyl)‐3‐methyl‐5‐hydroxymorfolin is supported by the calculated highest occupied molecular orbital spatial distribution and atomic charges calculations for electrochemically formed radical cation. Infrared spectroelectrochemistry performed during oxidation in acetonitrile/water also supported the formation of this product.The analytical method of FPM determination on glassy carbon electrode was developed using DPV with an attained limit of detection = 4.7 μmol/L in phosphate buffer of pH 9. The linear range of the calibration curve is from 7.0 to 107.00 μmol/L, correlation coefficient (r) = 0.9988.

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3,8-Diaromatic-1,10-Phenanthroline Derivatives: Structure and Photophysical Properties as a Function of Their Arms

Muñoz,

Peñaloza,

Guajardo

et al. 2024

Preprint

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The effects of 4,7-di(pyrrolidin-1-yl) substituents on the reduction and oxidation mechanisms of 1,10-phenanthrolines: New perspectives in tailoring of phenantroline derivatives

Cited by 3 publications

References 20 publications

Spectroelectrochemical Properties of 1,10‐Phenanthroline Substituted by Phenothiazine and Carbazole Redox‐active Units

Spectroelectrochemical Properties of 1,10‐Phenanthroline Substituted by Phenothiazine and Carbazole Redox‐active Units

Voltammetric study of new psychoactive substance 3‐fluorophenmetrazine

3,8-Diaromatic-1,10-Phenanthroline Derivatives: Structure and Photophysical Properties as a Function of Their Arms

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