Anion Radical of Carbonyl Compounds as Electrochemically Generated Base in Henry Reactions: 1,2-Acenaphthenedione

Mendkovich, A. S.; Nasybullina, Darya V.; Elinson, Michaïl N.; Mikhalchenko, Ludmila V.

doi:10.1149/1945-7111/ab9eb3

Cited by 5 publications

(2 citation statements)

References 26 publications

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“…Overall, these studies suggest that DMF is a better choice than MeCN for electrochemical cycling of 1 and 2 . This is likely due to its acidity being lower than that of MeCN, , which makes the DMF less susceptible to deprotonation by the radical anions. ,,− The initial CV studies also confirm that methylation at position 2 of BzNNN results in enhanced redox stability compared to that of the 1-substituted analogue, consistent with ref .…”

Section: Resultssupporting

confidence: 79%

Benzotriazoles as Low-Potential Anolytes for Non-aqueous Redox Flow Batteries

et al. 2022

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Non-aqueous redox flow batteries hold promise as a technology for electrochemical energy storage based on the large potential window of organic solvents compared to that of their aqueous counterparts. However, to date, the realization of this promise has been limited by a dearth of redox active molecules that leverage the full potential window of non-aqueous solvents. This report addresses this challenge through the development of an organic storage material based on the benzotriazole scaffold. Using a combination of iterative molecular design, organic synthesis, electrochemical evaluation, and density functional theory, a 2-aryl benzotriazole derivative is developed that exhibits a redox potential below −2 V (−2.3 V vs ferrocene/ferrocenium), a ≥0.4 M solubility in the electrolyte solution in all oxidation states, and stable electrochemical cycling in a prototype flow battery (≤90% capacity retention over 100 cycles, which represents approximately 505 h of cycling).

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Section: Resultssupporting

confidence: 79%

Benzotriazoles as Low-Potential Anolytes for Non-aqueous Redox Flow Batteries

et al. 2022

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“…The proposed mechanism of Asir et al. suggests the formation of a radical anion for the first reduction, located at the C=O bond of the imide moiety, resulting in a longer C=O bond [14f,15] . An additional disulfide group at the NMI results in a remarkable change in the electrochemical behaviour.…”

Section: Resultsmentioning

confidence: 99%

Unravelling the Mystery: Enlightenment of the Uncommon Electrochemistry of Naphthalene Monoimide [FeFe] Hydrogenase Mimics

et al. 2021

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[FeFe] hydrogenase mimicking complexes containing N‐substituted naphthalene monoimide (NMI) of peri‐substituted dichalcogenides as bridging ligands have been prepared and characterized using different spectroscopic as well as by X‐ray diffraction methods. The redox behaviour has been investigated by cyclic voltammetry, IR and UV‐Vis spectroelectrochemistry (IR and UV‐Vis SEC), electron paramagnetic resonance (EPR) spectroscopy and quantum chemical simulations. IR SEC and EPR experiments combined with DFT calculations revealed the non‐innocent character of the NMI bridging ligands. EPR spectroscopy was applied to study the singly and doubly reduced state. Chemical reduction with one equivalent of Cp*2Co revealed the formation of an organic radical with a g‐value of 2.0028 at room temperature. When two equivalents of Cp*2Co were used to carry out the second reduction, no EPR signal could be detected anymore. IR SEC measurements indicate the formation of an EPR‐silent dimeric structure after the second reduction.

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