Electropolymerization of phenol and aniline derivatives: Synthesis, characterization and application as electrochemical transducers

Santos, Cátia da Cruz; Pimenta, Thiago Coimbra; Thomasini, Ronaldo Luis; Verly, Rodrigo M.; Franco, Diego Leoni; Ferreira, Lucas Franco

doi:10.1016/j.jelechem.2019.05.045

Cited by 37 publications

(11 citation statements)

References 41 publications

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“…Da indicates the formation of a species which mass corresponds to the TGE trimer with additional modifications in the structure. The obtained results can indicate the formation of the trimer as a complex or condensation, which is known in the literature for tannins [37,38] or species that link the phenolic rings with the neighboring aryl ring via the C-O-C bond [39,40].…”

Section: Maldi-tof Msmentioning

confidence: 67%

“…The oxidation can also disintegrate the C-ring of genistein. Moreover, there are known species that link the phenolic rings with the neighboring aryl ring via the C-O-C bond [39,40]. Taking into account these facts, and the mass of the detected species, one can design a model of a hypothetical species possessing the following properties: high molecular weight, extra -OH group in the B-ring, disintegrated the C-ring, disintegrated thiolated linker of TGE, presence of the aryl-O-aryl linkage.…”

Section: Molecular Modeling and The Quantum Mechanical Density Functional Calculationsmentioning

confidence: 99%

See 1 more Smart Citation

Anti-Cancer and Electrochemical Properties of Thiogenistein—New Biologically Active Compound

Stolarczyk

Strzempek

Łaszcz

et al. 2021

IJMS

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Pharmacological and nutraceutical effects of isoflavones, which include genistein (GE), are attributed to their antioxidant activity protecting cells against carcinogenesis. The knowledge of the oxidation mechanisms of an active substance is crucial to determine its pharmacological properties. The aim of the present work was to explain complex oxidation processes that have been simulated during voltammetric experiments for our new thiolated genistein analog (TGE) that formed the self-assembled monolayer (SAM) on the gold electrode. The thiol linker assured a strong interaction of sulfur nucleophiles with the gold surface. The research comprised of the study of TGE oxidative properties, IR-ATR, and MALDI-TOF measurements of SAM before and after electrochemical oxidation. TGE has been shown to be electrochemically active. It undergoes one irreversible oxidation reaction and one quasi-reversible oxidation reaction in PBS buffer at pH 7.4.. The oxidation of TGE results in electroactive products composed likely from TGE conjugates (e.g., trimers) as part of polymer. The electroactive centers of TGE and its oxidation mechanism were discussed using IR supported by quantum chemical and molecular mechanics calculations. Preliminary in-vitro studies indicate that TGE exhibits higher cytotoxic activity towards DU145 human prostate cancer cells and is safer for normal prostate epithelial cells (PNT2) than genistein itself.

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Section: Maldi-tof Msmentioning

confidence: 67%

Section: Molecular Modeling and The Quantum Mechanical Density Functional Calculationsmentioning

confidence: 99%

Anti-Cancer and Electrochemical Properties of Thiogenistein—New Biologically Active Compound

Stolarczyk

Strzempek

Łaszcz

et al. 2021

IJMS

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“…The electropolymerization reaction taking place on the surface of GCE is proposed in Figure 1B. According to proposed reaction schemes of electropolymerization of similar phenol derivatives present in literature [10][11][12] phenol monomers are polymerized through phenol functional group forming a À OÀ bridge and no disturbance is observed on the neighboring alkyl group. Thus we propose that the electropolymerization of 1 takes place through hydroxyl group of the ring (Figure 1B).…”

Section: Resultsmentioning

confidence: 88%

“…Second aim of this work was to investigate electropolymerization and electrochemical characterization of HPBAs. Similar formations such as hydroxybenzenes are known to be easily electropolymerized on the surface of various working electrodes for different applications [10][11][12]. Thus we have focused on electropolymerization of HPBAs on glassy carbon electrodes (GCEs) for selective voltammetric determination of F À , and voltammetric characterization of polymer layers.…”

Section: Introductionmentioning

confidence: 99%

Hydrolytic Stability of Hydroxyphenyl Boronic Acids(HPBAs) and Employment of Poly(HPBAs) for Voltammetric Determination of Fluoride Levels in Dental Formulations and Beverages; Significance of Raw DPV Data for Chemometric Discrimination

et al. 2022

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Physicochemical and electrochemical properties of hydroxyphenyl boronic acids(HPBAs) and their use in fluoride determinations were investigated. HPBAs were electropolymerized at pH 1.0-11.0 in 40-60 %(v/v) methanol-buffer. Differential pulse voltammetry(DPV) determinations of fluoride (with 1.0 × 10 À 5 -1.0 × 10 À 4 M linearity based on potential shift) using poly(HPBAs) glassy carbon electrodes(GCEs) have À 45.49 to + 34.40 % error range. Significance of raw DPV data for chemometric discrimination was investigated by principle component analysis. This is the first demonstration of fluoride determination with poly(HPBAs)GCEs and chemometric discrimination of pharmaceutical formulations so far. Due to the lack of experimental data in literature, current findings will make a contribution to literature.

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“…Therefore, hydrochloric acid solution (0.1 mM, pH 4) was used for electrochemical polymerization of DOS and TOTM onto SPGEs. As shown in Figure S1 , the electropolymerization of DOS and TOTM is successful, as can be observed by the decrease in the anodic current after the first cycle (five scans of the 10th cycle), which is derived from the consumption of the monomer [ 20 ]. As can be seen in Figures S1 and S2 , the chemical shift of δ 8.03 ppm (singlet peak) indicates that carbon at position 4 of TOTM forms a covalent bond with DOS.…”

Section: Resultsmentioning

confidence: 99%

Hybrid Plasticizers Enhance Specificity and Sensitivity of an Electrochemical-Based Sensor for Cadmium Detection

Ruangsuj

Wanthongcharoen

Chaisriratanakul

et al. 2022

IJMS

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In addition to their use as an additive to improve physical properties of solvent polymeric membranes, plasticizers have a considerable impact on the specificity and sensitivity of membrane-modified electrochemical sensors. In this work, we aim at the hybridization of two different plasticizers using the electropolymerization technique in the development of a cadmium(II)-selective electrochemical sensor based on screen-printed gold electrode along with cyclic voltammetric measurement. At this point, we first screen for the primary plasticizer yielding the highest signal using cyclic voltammetry followed by pairing it with the secondary plasticizers giving rise to the most sensitive current response. The results show that the hybridization of DOS and TOTM with 3:1 weight ratio (~137.7-μm-thick membrane) renders a signal that is >26% higher than that from the sensor plasticized by DOS per se in water. The solution of 0.1 mM hydrochloric acid (pH 4) is the optimal supporting electrolyte. In addition, hybrid plasticizers have adequate redox capacity to induce cadmium(II) transfer from bulk solution to the membrane/water interfaces. Conversion of voltammetric signals to semi-integral currents results in linearity with cadmium(II) concentration, indicating the irreversible cadmium(II) transfer to the membrane. The DOS:TOTM hybrid sensor also exhibits high sensitivity, with a limit of detection (LOD) and limit of quantitation (LOQ) of 95 ppb and 288 ppb, respectively, as well as greater specificity towards cadmium(II) than that obtained from the single plasticizer sensor. Furthermore, recovery rates of spiked cadmium(II) in water samples were higher than 97% using the hybrid plasticizer sensor. Unprecedentedly, our work reports that the hybridization of plasticizers serves as ion-to-electron transducer that can improve the sensor performance in cadmium(II) detection.

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Electropolymerization of phenol and aniline derivatives: Synthesis, characterization and application as electrochemical transducers

Cited by 37 publications

References 41 publications

Anti-Cancer and Electrochemical Properties of Thiogenistein—New Biologically Active Compound

Anti-Cancer and Electrochemical Properties of Thiogenistein—New Biologically Active Compound

Hydrolytic Stability of Hydroxyphenyl Boronic Acids(HPBAs) and Employment of Poly(HPBAs) for Voltammetric Determination of Fluoride Levels in Dental Formulations and Beverages; Significance of Raw DPV Data for Chemometric Discrimination

Hybrid Plasticizers Enhance Specificity and Sensitivity of an Electrochemical-Based Sensor for Cadmium Detection

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