Heteroaromatic Radicals, Part II: Radicals with Group VI and Groups V and VI Ring Heteroatoms

Hanson, Peter

doi:10.1016/s0065-2725(08)60996-4

Cited by 26 publications

(3 citation statements)

References 531 publications

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“…The homospin, S = 1/2, RA salts of 1,2,5-chalcogenadiazoles were prepared with a number of reducing agents covering elemental potassium [74] (used previously for EPR experiments [57,58,59,60,61,62,63,64]), thiophenolate and its Se congener [77,78], tetrakis(dimethylamino)ethylene (TDAE) [76], and cobaltocene (CoCp 2 ) [75].…”

Section: Charge-transfer Complexes and Radical-ion Saltsmentioning

confidence: 99%

“…Whereas salts 76 and 77 are EPR-active in both the solid-state and solution, salt 78 is EPR-silent in these states of aggregation due to the substantial zero-field splitting and fast relaxation of the cation provoking fast relaxation of the RA [71,73]. In solution the salts exist most likely in the form of ion pairs which is typical of the discussed RAs [57,58,59,60,61,62,63,64].…”

Section: Charge-transfer Complexes and Radical-ion Saltsmentioning

confidence: 99%

“…Negatively charged chalcogen-nitrogen π-heterocyclic radicals ( i.e. , radical anions—RAs), though observed by EPR (S and Se derivatives) in the mid-1960s [18,56,57,58,59,60,61,62,63,64,65], were not used until recently in the design and synthesis of potentional functional materials because of the lack of methods for their isolation. The only related species were RAs of TCNQ-fused 1,2,5-thia(selena)diazoles isolated in the form of salts [66,67,68,69].…”

Section: Introductionmentioning

confidence: 99%

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Breathing Some New Life into an Old Topic: Chalcogen-Nitrogen π-Heterocycles as Electron Acceptors

et al. 2013

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Recent progress in the design, synthesis and characterization of chalcogennitrogen π-heterocycles, mostly 1,2,5-chalcogenadiazoles (chalcogen: S, Se and Te) and their fused derivatives, possessing positive electron affinity is discussed together with their use in preparation of charge-transfer complexes and radical-anion salts-candidate building blocks of molecule-based electrical and magnetic functional materials.

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Section: Charge-transfer Complexes and Radical-ion Saltsmentioning

confidence: 99%

Section: Charge-transfer Complexes and Radical-ion Saltsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Breathing Some New Life into an Old Topic: Chalcogen-Nitrogen π-Heterocycles as Electron Acceptors

et al. 2013

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Electron‐transfer Reactions of Heteroaromatic Compounds

Albini¹,

Fagnoni²

2001

Electron Transfer in Chemistry

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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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Heteroaromatic Radicals, Part II: Radicals with Group VI and Groups V and VI Ring Heteroatoms

Cited by 26 publications

References 531 publications

Breathing Some New Life into an Old Topic: Chalcogen-Nitrogen π-Heterocycles as Electron Acceptors

Breathing Some New Life into an Old Topic: Chalcogen-Nitrogen π-Heterocycles as Electron Acceptors

Electron‐transfer Reactions of Heteroaromatic Compounds

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

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