1-Vinylazulenes with Oxazolonic Ring-Potential Ligands for Metal Ion Detectors; Synthesis and Products Properties

Cristea, Mihaela; Bîrzan, Liviu; Dumitraşcu, Florea; Enache, Cristian; Tecuceanu, Victorița; Hanganu, Anamaria; Drăghici, Constantin; Deleanu, Călin; Nicolescu, Alina; Maganu, Maria; Razus, Alexandru C.

doi:10.3390/sym13071209

Cited by 6 publications

(8 citation statements)

References 14 publications

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“…Previous research on such azulene compounds has demonstrated that azulene-based monomers are promising compounds for the construction of modified electrodes designed for the detection of HMs [21]. The presence of the azulenyl moiety (able to undergo anodic polymerization) and the oxazol-5(4H)-one functional group (with high affinity for cations) leads to a higher electron density of this second group and, consequently, to push-pull structures useful to build complexing modified electrodes [22].…”

Section: Methodsmentioning

confidence: 99%

“…G was synthesized by condensation of the hippuric acid derivative with azulene-1-carbaldehyde [21]. The main features of G were checked: crystalline state, melting point (m.p.…”

Section: Methodsmentioning

confidence: 99%

“…Another interest in the study of this compound is its potential response in NLO or coloring properties [23,24]. Several azulenyl-phenyloxazolones were investigated for their optical properties [14,21]. Their encouraging performance stimulated our interest in studying G among other oxazolones.…”

Section: Introductionmentioning

confidence: 99%

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Chemically Modified Electrodes Based on 4-((5-Isopropyl-3,8-dimethylazulen-1-yl)methylene)-2-phenyloxazol-5(4H)-one

Brotea,

Matica,

Musina (Borsaru)

et al. 2024

Symmetry

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Novel chemically modified electrodes (CMEs) based on azulene were prepared by electrooxidation of guaiazulene derivative 4-((5-isopropyl-3,8-dimethylazulen-1-yl)methylene)-2-phenyloxazol-5(4H)-one (G). G is based on guaiazulene non-alternating aromatic hydrocarbon exhibiting a less symmetrical structure compared to naphthalene skeletal derivative. Therefore, it can be used as a building block for the preparation of novel materials. To evaluate the chemical structure and surface images, the CMEs based on G (G-CMEs) were characterized by ferrocene redox probe, X-ray photon spectroscopy (XPS), and scanning electron microscopy (SEM). They were also tested for the analysis of synthetic samples of heavy metal (HM) ions. The influence of preparation conditions (electric charge and potential) on the properties of these CMEs was examined. This paper highlights the importance of electropolymerization conditions on electrodeposited film surfaces, especially on their analytical properties vs. Cd(II), Pb(II), Cu(II), and Hg(II) investigated ions. This study is relevant for further design and development of advanced materials based on azulenyl-phenyloxazolone for the HM analysis in water. A linear dependence of the peak currents for Pb(II) ion on the concentration in test aqueous solutions was obtained between 10−7 M and 5·10−5 M. The detection limits of 5·10−6 M; 10−7 M; 5·10−6 M; and 10−5 M were estimated for Cd(II), Pb(II), Cu(II), and Hg(II), respectively, for G-CMEs.

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Section: Methodsmentioning

confidence: 99%

“…G was synthesized by condensation of the hippuric acid derivative with azulene-1-carbaldehyde [21]. The main features of G were checked: crystalline state, melting point (m.p.…”

Section: Methodsmentioning

confidence: 99%

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Chemically Modified Electrodes Based on 4-((5-Isopropyl-3,8-dimethylazulen-1-yl)methylene)-2-phenyloxazol-5(4H)-one

Brotea,

Matica,

Musina (Borsaru)

et al. 2024

Symmetry

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“…All the solvents were of spectroscopic grade and were commercially acquired from Sigma-Aldrich. The azulene derivatives (Table S1) were prepared following a previ-ously reported synthetic method based on the condensation of azulene-1-carbaldehydes with hippuric acids by Erlenmeyer-Plöchl synthesis [33] (Figure 3). Copper sulfate pentahydrate, cadmium sulfate hydrate, lead(II) acetate trihydrate and mercury(II) chloride (Sigma-Aldrich) were utilized as received.…”

Section: Methodsmentioning

confidence: 99%

Solvent Effects and Metal Ion Recognition in Several Azulenyl-Vinyl-Oxazolones

Homocianu¹,

Airinei²,

Matica

et al. 2023

Symmetry

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The spectral properties of several azulene-oxazolone derivatives containing a phenyloxazolone moiety linked to a substituted azulene ring via a C=C double bond were studied in different solvents of varying polarity. The solvatochromism and the ability of azulene-oxazolone derivatives to recognize heavy metal ions were investigated. In order to estimate the contribution of the non-specific and specific solute–solvent interactions, multiple linear regression analysis using Kamlet–Taft, Catalan and Laurence parameters was applied. These azulene derivatives demonstrate positive solvatochromism. The methyl and isopropyl substituents at the seven-membered azulene ring determine the highest red shifts of the absorption maxima of these azulenyl-vinyl-oxazolones. According to Catalan and Laurence models, the solvent polarizability is a more significant parameter in describing the solvatochromic properties of the azulene-oxazolone derivatives. The azulene-oxazolone compounds under study showed a good response to heavy metal cations (Cd2+, Hg2+, Cu2+ and Pb2+).

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“…T (Figure 1) is part of the diazenes recently studied by our research group [7], which synthesizes various functionalized azulene derivatives for future applications [14]. Azulene is an interesting building block for the synthesis of new advanced materials [15], as it shows low ionization energy and high electron mobility among the classical electropolymerizable monomers (pyrrole, thiophene, etc.)…”

Section: Introductionmentioning

confidence: 99%

Surface Characterization of New Azulene-Based CMEs for Sensing

et al. 2021

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Films of 2-(azulen-1-yldiazenyl)-5-phenyl-1,3,4-thiadiazole (T) were successfully deposited on glassy carbon surfaces to prepare chemically modified electrodes (CMEs). Their surface characterization was analyzed by electrochemical impedance spectroscopy (EIS), atomic force microscopy (AFM), and scanning electron microscopy (SEM). This complexing monomer has been deposited through direct electropolymerization in conditions established during the electrochemical characterization of T performed by cyclic voltammetry (CV), differential pulse voltammetry (DPV) and rotating disk electrode voltammetry (RDE). These methods put in evidence the high degree of asymmetry of oxidation and reduction curves, which is due to the irreversible processes occurring at opposite potentials. The film formation was confirmed by ferrocene redox assay probe. The properties of the electrodes modified with T (T-CMEs) were investigated for sensing heavy metal (HM) ions in water solutions, with promising results for Pb(II) among Cd(II), Cu(II), and Hg(II) ions.

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1-Vinylazulenes with Oxazolonic Ring-Potential Ligands for Metal Ion Detectors; Synthesis and Products Properties

Cited by 6 publications

References 14 publications

Chemically Modified Electrodes Based on 4-((5-Isopropyl-3,8-dimethylazulen-1-yl)methylene)-2-phenyloxazol-5(4H)-one

Chemically Modified Electrodes Based on 4-((5-Isopropyl-3,8-dimethylazulen-1-yl)methylene)-2-phenyloxazol-5(4H)-one

Solvent Effects and Metal Ion Recognition in Several Azulenyl-Vinyl-Oxazolones

Surface Characterization of New Azulene-Based CMEs for Sensing

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