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Нуретдинов, И. А.; Yanilkin, V. V.; Морозов, В. И.; Gubskaya, V. P.; Зверев, В. В.; Nastapova, N. V.; Fazleeva, G. M.

doi:10.1023/a:1015499425490

Cited by 16 publications

(10 citation statements)

References 13 publications

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“…34 This involves a nucleophilic attack of the anions of bromo(dialkoxyphosphoryl)methoxy carbonylmethanes on fullerene. 17,35,36 In our case, we suggest bonding be tween the addends in the dimers. The rate of such reactions will be determined by the nucleophilicity of the carbanion, the electrophilicity of the electrophile, and the steric factor.…”

Section: Methodsmentioning

confidence: 56%

Phosphorylated methano[60]fullerenes containing nitroxyl radicals: synthesis, structures, and electrochemical behavior

et al. 2005

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Phosphorylated methano[60]fullerenes containing one or two nitroxyl radicals were syn thesized for the first time. Their structures were established from spectroscopic data and their compositions, by MALDI TOF mass spectrometry. Their electrochemical reduction in a sys tem o dichlorobenzene-DMF/0.1 M Bu 4 NBF 4 was studied by cyclic voltammetry, prepara tive electrolysis, and ESR spectroscopy in combination with in situ electrolysis. Both com pounds were found to undergo four step reduction of the fullerene sphere, reduction of ni troxyl, opening of the three membered ring, and elimination of addends as carbanions stabi lized by protonation and rearrangement into phosphate ions and substituted acetylene, which are accompanied by the formation of free fullerene and dihydrofuranofullerene. The rates of the ring opening and the addend elimination increased with an increase in the negative charge on the fullerene sphere. These reactions are fast in the case of transfer of three electrons. With the use of model compounds, heterogeneous electron transfer to the nitroxyl radical at the potentials of the transfer of the third electron to the fullerene sphere and homogeneous in tramolecular electron transfer from the dianion of the fullerene sphere were revealed. The mechanisms of the observed transformations are discussed.

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Section: Methodsmentioning

confidence: 56%

Phosphorylated methano[60]fullerenes containing nitroxyl radicals: synthesis, structures, and electrochemical behavior

et al. 2005

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“…11, 16 In the me dium under study, the cyclic voltammograms show three reduction peaks, and three conjugated oxidation peaks are observed on the reverse scan of the cyclic voltammo grams (see Table 1). 11, 16 In the me dium under study, the cyclic voltammograms show three reduction peaks, and three conjugated oxidation peaks are observed on the reverse scan of the cyclic voltammo grams (see Table 1).…”

Section: Resultsmentioning

confidence: 93%

Synthesis of new carbazole-containing fullerenopyrrolidines

et al. 2005

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The reactions of fullerene C 60 and N methylglycine with 3 formyl 9 isoamylcarbazole or 3,6 diformyl 9 isoamylcarbazole afforded new carbazole containing fullerenopyrrolidines. Their structures were established by spectroscopic methods. Electrochemical reduction and oxidation of the resulting compounds were studied by cyclic voltammetry and ESR spectro scopy. The three dimensional structures were determined by the quantum chemical PM3 and DFT/PBE/TZ2P methods.

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“…Cyclic voltammetric data (reduction peak potentials (E p,red ) and oxidation peak potentials (E p,ox )) for electrochemical reduction of C 60 and fullerenopyrrolidines 5-8 in an DCB-DMF Electrochemical reduction of fullerenopyrrolidines 7 and 8 proceeds analogously to reduction of the represen tatives of this class of [60]fullerene derivatives studied earlier. 13, 14 The cyclic voltammograms show three reduc tion peaks as well as three conjugated oxidation peaks on the reverse scan (Table 1, Fig. 3).…”

Section: Resultsmentioning

confidence: 97%

“…The absorption band at 430 nm is indicative of the forma tion of [6,6] closed monoadducts. 11- 14 The IR spectra of these compounds show absorption bands at 525 and 1425 cm -1 belonging to vibrations of the fullerene cage and a number of other bands corresponding to stretching vibrations of the attached fragments. The spectra of all compounds contain absorption bands of P=S groups at 775-800 cm -1 .…”

Section: Resultsmentioning

confidence: 99%

Synthesis, structures, and properties of new thiophosphorylated fullerenopyrrolidines. First example of the Pishchimuka reaction in fullerene derivatives

et al. 2006

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The reactions of fullerene C 60 with thiophosphorylated mono or dialdehydes and N methylglycine in toluene afforded new thiophosphorylated fullerenopyrrolidines, including those containing the free aldehyde group. The purity and compositions of the reaction products were confirmed by MALDI TOF mass spectrometry and HPLC. The structures of the reaction products were established by two dimensional homo and heterocorrelation NMR experi ments. The properties of the products were studied by cyclic voltammetry and quantum chemi cal methods. The Pishchimuka rearrangement in thiophosphorylated derivatives of fullereno pyrrolidines was performed for the first time, and thiol esters of phosphonic acids of fullerenopyrrolidines were prepared.

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Cited by 16 publications

References 13 publications

Phosphorylated methano[60]fullerenes containing nitroxyl radicals: synthesis, structures, and electrochemical behavior

Phosphorylated methano[60]fullerenes containing nitroxyl radicals: synthesis, structures, and electrochemical behavior

Synthesis of new carbazole-containing fullerenopyrrolidines

Synthesis, structures, and properties of new thiophosphorylated fullerenopyrrolidines. First example of the Pishchimuka reaction in fullerene derivatives

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