Radical anion and coordination compounds of polyconjugated molecules:potential organic materials with unusual magnetic, conducting and optical properties

Konarev, Dmitri V.

doi:10.1016/j.mencom.2020.05.001

Cited by 10 publications

(3 citation statements)

References 144 publications

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“…These include, for example, the formation of Grignard reagents, [5] S RN 1 reactions, [6,7] DNA damage, [8,9] and enzymatic reactions [10] . They are also used for the synthesis of materials [11,12] for various applications and have understandably been intensively investigated both experimentally [5–12] and theoretically [13,14] . Of particular importance is the understanding of the effect of substituents on the formation and subsequent dissociation of radical ions.…”

Section: Introductionmentioning

confidence: 99%

New Insights into the Substituents’ Effect on the Formation and Dissociation of Radical Anions: Dissociative Electron Transfer to Arylsulfonylphthalimides

2021

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The electrochemical reduction of a series of biologically relevant p‐substituted arylsulfonylphthalimides was investigated and the results were analysed using theoretical calculations and application of Savéant's dissociative electron transfer theory. The dissociation rate constants of the radical anion intermediates were calculated and showed that upon changing the substituent from the MeO, to Me, H, F, Cl and CN the dissociation became faster. A good correlation with the Hammett substituent constants was also obtained. With the NO2 substituent the trend was however inversed. These results and the electrolysis data showed that the dissociation involves the N−S chemical bond. Theoretical calculations showed that for all investigated compounds the extra electron was hosted by the phthalimidyl group except for the p‐NO2 substituted compound for which the extra electron was hosted by the nitrophenyl moiety. Thermodynamic considerations showed that the dissociation of the radical anion of the p‐NO2 compound followed a heterolytic cleavage whereas those of the rest of the investigated compounds followed a homolytic cleavage. The above intriguing result was rationalized through application of the extension of Savéant's dissociative electron transfer theory to the decomposition of radical anions. This study is important not only for understanding substituents’ effect on the biological activity of these compounds but also on the formation and dissociation of radical anions in general.

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Section: Introductionmentioning

confidence: 99%

New Insights into the Substituents’ Effect on the Formation and Dissociation of Radical Anions: Dissociative Electron Transfer to Arylsulfonylphthalimides

2021

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“…However, the solubility of large aromatic molecules can be enhanced in forms of coordination complexes and in reduced anionic forms. 28,29 First and second reduction potentials are known for 2,3,8,9,14,15-hexamethyl-HATNA: −1.09 and −1.40 V ( vs. SCE), respectively. 30 The coordination of metals to these ligands can partially shift their redox potentials to positive values.…”

Section: Resultsmentioning

confidence: 99%

Manganese(ii) complexes of hexaazatrinaphthylene and hexaazatrianthracene: synthesis, structure and properties

Mikhailenko,

Ivanov,

Faraonov

et al. 2023

New J. Chem.

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“…However, the solubility of large aromatic molecules is greatly enhanced in reduced anionic forms. 22,23 HAT(CN) 6 and HATNA(CN) 6 ligands have similar acceptor properties. 17 In addition, HAT (CN) 6 has first and second reduction potentials at −0.48 and −0.93 V (vs. Ag/Ag + ).…”

Section: Synthesismentioning

confidence: 99%

Magnetic behavior and ground spin states for coordination {L·[M^II(Hal)₂]₃}³⁻ assemblies (Hal = Cl or I) of radical trianion hexacyanohexaazatriphenylenes (L) with three coordinated high-spin Fe^II (S = 2) or Co^II (S = 3/2) centers

et al. 2023

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Radical anion and coordination compounds of polyconjugated molecules:potential organic materials with unusual magnetic, conducting and optical properties

Cited by 10 publications

References 144 publications

New Insights into the Substituents’ Effect on the Formation and Dissociation of Radical Anions: Dissociative Electron Transfer to Arylsulfonylphthalimides

New Insights into the Substituents’ Effect on the Formation and Dissociation of Radical Anions: Dissociative Electron Transfer to Arylsulfonylphthalimides

Manganese(ii) complexes of hexaazatrinaphthylene and hexaazatrianthracene: synthesis, structure and properties

Magnetic behavior and ground spin states for coordination {L·[M^II(Hal)₂]₃}³⁻ assemblies (Hal = Cl or I) of radical trianion hexacyanohexaazatriphenylenes (L) with three coordinated high-spin Fe^II (S = 2) or Co^II (S = 3/2) centers

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Radical anion and coordination compounds of polyconjugated molecules:potential organic materials with unusual magnetic, conducting and optical properties

Cited by 10 publications

References 144 publications

New Insights into the Substituents’ Effect on the Formation and Dissociation of Radical Anions: Dissociative Electron Transfer to Arylsulfonylphthalimides

New Insights into the Substituents’ Effect on the Formation and Dissociation of Radical Anions: Dissociative Electron Transfer to Arylsulfonylphthalimides

Manganese(ii) complexes of hexaazatrinaphthylene and hexaazatrianthracene: synthesis, structure and properties

Magnetic behavior and ground spin states for coordination {L·[MII(Hal)2]3}3− assemblies (Hal = Cl or I) of radical trianion hexacyanohexaazatriphenylenes (L) with three coordinated high-spin FeII (S = 2) or CoII (S = 3/2) centers

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Magnetic behavior and ground spin states for coordination {L·[M^II(Hal)₂]₃}³⁻ assemblies (Hal = Cl or I) of radical trianion hexacyanohexaazatriphenylenes (L) with three coordinated high-spin Fe^II (S = 2) or Co^II (S = 3/2) centers