Photochemistry of 1,3,2,4-benzodithiadiazines: formation and oxidation of 1,2,3-benzodithiazolyl radicals

Gritsan, Nina P.; Kim, Stanislav N.; Makarov, Alexander Yu.; Чесноков, Е. Н.; Zibarev, Andrey V.

doi:10.1039/b510188c

Cited by 23 publications

(6 citation statements)

References 28 publications

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“…The DFT approach at the (U)B3LYP/6‐31+G(d)39, 40 level of theory was used for the calculations since it performs well for molecular structures and properties of main‐group compounds including electron affinities and hyperfine coupling constants 20, 41, 42. Previously, the (U)B3LYP method was successfully employed to reproduce the properties of a series of both closed‐ and open‐shell chalcogen–nitrogen cycles and cages including RAs 25–31, 43–50. Quantum chemical calculations on RAs and their neutral precursors were carried out with full geometry optimization using the GAMESS51 and GAUSSIAN‐0352 programs.…”

Section: Methodsmentioning

confidence: 99%

Redox properties and radical anions of fluorinated 2,1,3‐benzothia(selena)diazoles and related compounds

Vasilieva

Irtegova

Gritsan

et al. 2010

J of Physical Organic Chem

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In comparison with 2,1,3‐benzothia(selena)diazoles, electrochemical oxidation and reduction of their 4,5,6,7‐tetrafluoro derivatives and a number of related compounds were studied by cyclic voltammetry. For nine examples of this class, the first reduction peaks are reversible and corresponding radical anions (RAs) are long‐lived at 295 K in MeCN and especially in DMF. The oxidation peaks were irreversible and corresponding radical cations were not observed. Electrochemically generated RAs were characterized by EPR measurements and DFT calculations at the UB3LYP/6‐31+G(d) level. The spin density distribution in the RAs is analyzed in connection with effects of S substitution by Se and/or H by F. The prospects of the studied RAs in the design and synthesis of magnetically active materials are discussed. Copyright © 2010 John Wiley & Sons, Ltd.

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Section: Methodsmentioning

confidence: 99%

Redox properties and radical anions of fluorinated 2,1,3‐benzothia(selena)diazoles and related compounds

Vasilieva

Irtegova

Gritsan

et al. 2010

J of Physical Organic Chem

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“…Therefore, one may speculate whether trace amountso fa tmosphericH 2 Oo r/and O 2 are somehow involved. [13,22] The mechanism of decay of [3]C À was analyzed with respect to molecular association through secondary bonding interactions Te ···Nt ypicalo ft elluradiazoles. [1d, 23, 24] However,w ith DFT arealistic pathway of the decay was not found (see Supporting Information).…”

Section: Chemical Reductionmentioning

confidence: 99%

Radical Anions, Radical‐Anion Salts, and Anionic Complexes of 2,1,3‐Benzochalcogenadiazoles

Pushkarevsky

Chulanova

Shundrin

et al. 2018

Chemistry A European J

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With cyclic voltammetry (CV) and DFT calculations, it was found that electron acceptor ability of the 2,1,3-benzochalcogenadiazoles 1-3 (chalcogen: S, Se and Te, respectively) increases with the atomic number of chalcogen. This trend is nontrivial since it contradicts the electronegativity and atomic electron affinity of the chalcogens. In contrast to radical anions (RAs) [1]*- and [2]*-, RA [3]*- was not detected by EPR under the CV conditions. Chemical reduction of 1-3 was performed and new thermally-stable RA salts [K(THF)]+[2]*- (8) and [K(18-crown-6)]+[2]*- (9) were isolated in addition to known salt [K(THF)]+[1]*- (7). Upon contact with air, RAs [1]*- and [2]*- underwent fast decomposition in solution with the formation of anions [ECN]- isolated in the form of salts [K(18-crown-6)]+[ECN]- (10, E = S; 11, E = Se). In the case of 3, RA [3]*- was detected by EPR to be the first representative of tellurium-nitrogen π-heterocyclic RAs but not isolated. Instead, salt [K(18-crown-6)]+2[3-Te2]2- (12) featuring a new anionic complex with the coordinate bond Te-Te was obtained. Upon contact with air, salt 12 transformed into salt [K(18-crown-6)]+2[3-Te4-3]2- (13) revealing an anionic complex with two coordinate bonds Te-Te. The structures of 8-13 were confirmed by X-ray diffraction and the nature of the coordinate bonds Te-Te in [3-Te2]2- and [3-Te4-3]2- was studied with DFT calculations and QTAIM analysis.

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“…Phenoxynaphthacenequinones are well-known photochromic species which undergo reversible photochemical isomerization between trans-quinone and ano-quinone isomeric forms [88][89][90][91][92], Figure 17A. While their optical photochromic features have been studied in details [88,90], their switchable electrochemical properties associated with the photoisomerization processes are studied only fragmentally. The most comprehensive study of the photo-switchable electrochemical properties of the transand ano-isomeric forms was performed for their mono- 3 4 5 6 7 8 9 10 11 12 13 14 15 16 17 18 19 20 21 22 23 24 25 26 27 28 29 30 31 32 33 34 35 36 37 38 39 40 41 42 43 44 45 46 47 48 49 50 51 52 53 54 55 56 57 58 layer immobilized molecules [93,94].…”

Section: Phenoxynaphthacenequinone-based Photoelectrochemical Switchesmentioning

confidence: 99%

Modified Electrodes and Electrochemical Systems Switchable by Light Signals

Katz¹

2018

Electroanalysis

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This article is an overview of extensive research efforts in many laboratories in the last two decades in the area of light‐switchable electrochemical systems and modified electrodes. Electrochemical reactions, including electrocatalytic and bioelectrocatalytic processes, have been reversibly activated and inhibited upon irradiation with light at different wavelengths. In order to realize these light activated or inhibited processes, the electrodes or/and reacting molecules were functionalized with photoisomerizable molecules including various derivatives of diarylethene, phenoxynaphthacenequinone, azobenzene and spiropyran/merocyanine. Photochemical reactions of these species resulted in change of their redox activity, conformation and electrical charge. All these changes affected electrode surfaces or (bio)molecules resulting in switching ON‐OFF corresponding (bio)electrochemical processes. Various systems based on different light‐controlled reactions are reviewed and discussed with specific examples and with many illustrating figures. Possible extensions of the research area and future applications are briefly overviewed in the conclusion section. The present comprehensive review is addressed to a broad scientific community, including newcomers to the area.

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Photochemistry of 1,3,2,4-benzodithiadiazines: formation and oxidation of 1,2,3-benzodithiazolyl radicals

Cited by 23 publications

References 28 publications

Redox properties and radical anions of fluorinated 2,1,3‐benzothia(selena)diazoles and related compounds

Redox properties and radical anions of fluorinated 2,1,3‐benzothia(selena)diazoles and related compounds

Radical Anions, Radical‐Anion Salts, and Anionic Complexes of 2,1,3‐Benzochalcogenadiazoles

Modified Electrodes and Electrochemical Systems Switchable by Light Signals

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