Synthesis and evaluation of photophysical and electrochemical properties of vinyl chalcogenide derivatives of phenothiazines

Dilelio, Marina C.; Kaufman, Teodoro S.; Iglesias, Bernardo A.; Silveira, Cláudio C.

doi:10.1016/j.dyepig.2021.109982

Cited by 3 publications

(7 citation statements)

References 43 publications

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“…When excited at 291 nm, molecule 2a shows an emission band with two peaks at 434 nm and 457 nm. Its profile of phosphorescence is similar to the phosphorescence spectra of pure 10 H -phenothiazine (λ 500 nm [ 50 ], λ 535 nm [ 52 ]). Similar to absorption and fluorescence, it is clear that the phosphoryl moiety in compound 2a causes a large hypsochromic effect (c.a.…”

Section: Resultsmentioning

confidence: 67%

“…In addition, we can observe a band below 200 nm, similar to other phenothiazines [ 49 ]. In comparison with 10 H -phenothiazine (λ max = 252 nm and 316 nm [ 50 ]), the presence of N -phosphoryl substituent in compound 2a caused a hypsochromic effect. Non-planar structure of 2a makes the n-π assignment questionable.…”

Section: Resultsmentioning

confidence: 99%

“…The fluorescent band of compound 2a ( Figure 9 ) is located at 374 nm, and it is also blue-shifted in comparison with the emission band of 10 H -phenothiazine (λ em = 454 nm [ 50 ]) and N -methyl-phenothiazine (λ em = 450 nm [ 51 ]). The TDDFT calculations for molecule 2a clearly indicate the observed emission band at 374 nm ( Figure 9 ), which corresponds to the vertical S 1 →S 0 transition calculated at 386 nm ( Table S2, Supplementary Materials ).…”

Section: Resultsmentioning

confidence: 99%

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Synthesis and Spectroscopic Characterization of Selected Phenothiazines and Phenazines Rationalized Based on DFT Calculation

et al. 2022

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Two unique structures were isolated from the phosphorylation reaction of 10H-phenothiazine. The 5,5-dimethyl-2-(10H-phenothiazin-10-yl)-1,3,2-dioxaphosphinane 2-oxide (2a) illustrates the product of N-phosphorylation of phenothiazine. Moreover, a potential product of 2a instability, a thiophosphoric acid 2b, was successfully isolated and structurally characterized. Molecule 2a, similarly to sulfoxide derivative 3, possesses interesting phosphorescence properties due to the presence of d-pπ bonds. The X-ray, NMR, and DFT computational studies indicate that compound 2a exhibits an anomeric effect. Additionally, the syntheses of selected symmetrical and unsymmetrical pyridine-embedded phenazines were elaborated. To compare the influence of phosphorus and sulfur atoms on the structural characteristics of 10H-phenothiazine derivatives, the high-quality crystals of (4a,12a-dihydro-12H-benzo[5,6][1,4]thiazino[2,3-b]quinoxalin-12-yl)(phenyl)methanone (1) and selected phenazines 5,12-diisopropyl-3,10-dimethyldipyrido[3,2-a:3′,2′-h]phenazine (5) and 5-isopropyl-N,N,3-trimethylpyrido[3,2-a]phenazin-10-amine (6a) were obtained. The structures of molecules 1, 2a, 2-mercapto-5,5-dimethyl-1,3,2-dioxaphosphinane 2-oxide (2b), 3,7-dinitro-10H-phenothiazine 5-oxide (3), 5 and 6a were determined by single-crystal X-ray diffraction measurements.

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Section: Resultsmentioning

confidence: 67%

Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

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Synthesis and Spectroscopic Characterization of Selected Phenothiazines and Phenazines Rationalized Based on DFT Calculation

et al. 2022

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“…Some of these compounds presented biological activities [21] and symmetric bis-vinyl sulfides also displayed interesting photophysical properties. [22] Therefore, Table 2. Synthesis of 3-substituted indoles with vinylsulfides.…”

Section: Resultsmentioning

confidence: 99%

“…Bis‐vinyl sulfides have also been previously described by our research group. Some of these compounds presented biological activities [21] and symmetric bis‐vinyl sulfides also displayed interesting photophysical properties [22] . Therefore, encouraged by these previous results, we decided to prepare some bis‐vinyl sulfides derived from indole 3‐carbaldehydes.…”

Section: Resultsmentioning

confidence: 99%

A Convenient Wittig‐Horner Mediated Synthesis of 3‐Vinylsulfide Derivatives of Indoles

et al. 2022

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A simple and robust coupling protocol is reported to provide the previously unknown indole derivatives carrying vinylsulfide motifs attached to C−3 of the heterocycle. The developed strategy involved a Wittig‐Horner reaction with different phosphinoxide derivatives. The reaction conditions were optimized and its scope and limitations were assessed. The target compounds, including 3‐arylvinylsulfides as well as symmetric and dissymmetric bis‐vinylsulfides, were obtained in a straightforward way, as mixtures of geometric isomers, in good to excellent yields.

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A High‐Potential Bipolar Phenothiazine Derivative Cathode for Aqueous Zinc Batteries

Wang

Qiu

et al. 2023

ChemSusChem

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Aqueous zinc ion batteries (AZIBs) are gaining popularity as advanced energy storage devices that are economical, safe, and use resource‐abundant storage options. In this study, we have synthesized a bipolar phenothiazine organic scaffold known as 3,7‐bis(melaminyl)phenothiazin‐5‐ium iodide (PTDM), which is obtained by undergoing nucleophilic substitution through phenothiazinium tetraiodide hydrate (PTD) and melamine. Electrochemical results indicate that PTDM can act as a high‐potential cathode material for rechargeable AZIBs. In detail, the aqueous PTDM//Zn full cell exhibits a high average voltage of approximate 1.13 V, along with a specific capacity of 118.3 mAh g−1 at 0.1 A g−1. Furthermore, this demonstrated cell displays moderate long‐term cycling stability over 6400 cycles, which is encouraging and suggests potential for developing advanced organic electrode materials for rechargeable AZIBs.

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Synthesis and evaluation of photophysical and electrochemical properties of vinyl chalcogenide derivatives of phenothiazines

Cited by 3 publications

References 43 publications

Synthesis and Spectroscopic Characterization of Selected Phenothiazines and Phenazines Rationalized Based on DFT Calculation

Synthesis and Spectroscopic Characterization of Selected Phenothiazines and Phenazines Rationalized Based on DFT Calculation

A Convenient Wittig‐Horner Mediated Synthesis of 3‐Vinylsulfide Derivatives of Indoles

A High‐Potential Bipolar Phenothiazine Derivative Cathode for Aqueous Zinc Batteries

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