Efficient 2 + 3 Cycloaddition Approach to Synthesis of Pyridinyl Based [60]Fullerene Ligands

Troshin, Pavel A.; Troyanov, Sergey I.; Boǐko, G. N.; Lyubovskaya, Rimma N.; Lapshin, A. N.; Gol’dshleger, N. F.

doi:10.1081/fst-120027200

Cited by 30 publications

(22 citation statements)

References 10 publications

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“…Very recently we have synthesized and structurally characterized a dyad formed from pyrrolidinofullerene 2 and ZnTPP that possesses a coordinative bond between the pyrrolidine N atom and the Zn of the metalloporphyrin. [8] A cyclic voltammetry study of the synthesized pyrrolidinofullerenes has revealed a correlation between the structures of the fullerene derivative and their reduction potentials. Electronic communication between the 2-pyridyl groups attached to the pyrrolidine ring and fullerene cage was found to be responsible for a negative shift of the reduction potentials.…”

Section: Discussionmentioning

confidence: 99%

“…The cis-arrangement of the pyridyl groups in 2 was revealed by the X-ray single crystal structure of a 1:1 complex of 2 with ZnTPP (ZnTPP = mesotetraphenylporphyrinatozinc) that was reported very recently. [8] A careful examination of the products formed in the reaction of 1.5 g of C 60 with 2-picolylamine and 2-pyridinecarbaldehyde allowed us to isolate a small amount (45 mg vs. 960 mg of 2) of the trans-isomer 2Ј,5Ј-di(2-pyridyl)pyrrolidino[3Ј,4Ј:1,2][60]fullerene (5) with a yield of about 4-5 %. The yields of the trans isomers of pyrrolidinofullerenes 1, 3, and 4 were too low to permit their isolation and spectroscopic characterization.…”

Section: -Picolylamine and N-substituted 2-picolylamines As Substratesmentioning

confidence: 99%

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An Efficient [2+3] Cycloaddition Approach to the Synthesis of Pyridyl‐Appended Fullerene Ligands

Troshin

Peregudov

Mühlbacher³

et al. 2005

Eur J Org Chem

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We have used 2-, 3-, and 4-picolylamines and their various N-substituted derivatives as substrates to generate azomethine ylides for [2+3] cycloaddition to [60]fullerene. A considerable difference in the reactivity of isomeric picolylamines was observed; however, even less reactive 3-picolylamines afford high yields of products under acid or base catalysis. This method provides easy access to a large family of valuable ligands (pyridyl-substituted pyrrolidinofullerenes) that can be used in the design of transition-metal complexes

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Section: Discussionmentioning

confidence: 99%

Section: -Picolylamine and N-substituted 2-picolylamines As Substratesmentioning

confidence: 99%

An Efficient [2+3] Cycloaddition Approach to the Synthesis of Pyridyl‐Appended Fullerene Ligands

Troshin

Peregudov

Mühlbacher³

et al. 2005

Eur J Org Chem

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“…1). 36 The coordination mode of the elec tron donor and acceptor components in this complex will be discussed below.…”

Section: Picolylamine and N Substituted 2 Picolylamines As Reactantsmentioning

confidence: 99%

New pyrrolidine and pyrroline derivatives of fullerenes: from the synthesis to the use in light-converting systems

et al. 2008

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The results of the authors' studies on the [2+3] cycloaddition of azomethine and nitrile ylides generated from picolylamine and benzylamine derivatives to fullerenes are systematized and new experimental data are considered. Catalysts and microwave radiation promoting the formation of ylides and their addition to fullerenes were successfully used for the first time. A large series of new pyrrolidine and pyrroline derivatives of fullerenes C 60 and C 70 were synthesized and characterized. The proposed procedures afford the reaction products in yields twice as high (80-85%) as those attained by the classical Prato reaction. The reactions proceed with virtually complete regio (in the case of C 70 ) and stereoselectivity to afford only cis 2´,5´ disubstituted and trans 1´,2´,5´ trisubstituted pyrrolidinofullerenes. Pyridyl substituted pyrrolidinofullerenes react with metalloporphyrins and phthalocyanines to form self ordered coordination complexes. The latter are analogs of natural photosynthetic antenna systems due to photoinduced charge separation that occurs in these complexes upon exposure to light.

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“…8 The spectral characteristics of the pyridyl containing fullerenopyrrolidines corresponded to literature data. Fullerene С 60 with 99.5% purity and TOAB (98%, Lancaster) were used.…”

Section: Methodsmentioning

confidence: 92%

Structure of electroactive coatings based on fullerene and its derivatives

et al. 2008

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The structures and properties of electroactive coatings based on fullerene and pyridyl substituted fullerenopyrrolidines were studied using cyclic voltammetry, optical spectroscopy, atomic force microscopy, and other methods. The surface of the electrode of the ITO conduct ing glass (alloy of indium and tin oxides) was modified by direct casting or the introduction of an electroactive substance into a tetra(n octyl)ammonium bromide matrix. Changes in the absorption spectra of the coatings agree with the presence of an electronic interaction between adjacent fullerene molecules. Tetra(n octyl)ammonium bromide is involved in the organiza tion of the fullerene containing coatings with retention of the layered structure. According to the data of atomic force microscopy, the coating surface depends on both the composition of the solution and preparation method and the nature of addends in a C 60 molecule. The dispersion of fullerene in the tetra(n octyl)ammonium bromide matrix and its interaction with the alkyl groups of the latter provide the hydrophobic microenvironment necessary for revers ible electrochemical processes in an aqueous solution to occur. Key words: electroactive coatings, [60]fullerene, cis 3 (4 imidazol 1 ylphenyl 1 (2 pyridyl)[60]fullereno[1,2 с]pyrrolidine, cis 1,3 di(2 pyridyl)[60]fullereno[1,2 с]pyrrolidine, cis 1,3 di(4 pyridyl)[60]fullereno[1,2 с]pyrrolidine, tetra(n octyl)ammonium bromide, self organization, cyclic voltammetry, atomic force microscopy, absorption spectra.The discovery of a new class of carbon nanoclusters (fullerenes) with the unique structure and spherical shape of the molecules and the development of methods for their preparation in rather large amounts were the begin ning of comprehensive investigation of these objects. Fullerenes and their derivatives, including fullereno pyrrolidines, are suitable "building blocks" for multicom ponent systems that demonstrate the ability to photoin duced energy and electron transfer. They are already used for the creation of molecular electronic devices. 1-4 New electrocatalysts on the basis of fullerenes and carbon nanotubes are developed and a possibility of creation of electrochemical sensors is studied. 5 Fullerenes are soluble in membranes and involved in electron transport through membranes. The ability to reversible electron transfer allows fullerenes to act as carriers both independent and combined with other mediators. 6 We have previously 7 studied the electrochemical be havior of fullerene C 60 and pyridyl substituted fullereno pyrrolidines for different methods of their immobilization on electrodes. The influence of the substituent in fullerenopyrrolidine on kinetics and thermodynamics of redox transformations of rubbed on films of individual fullerenes* during cathodic doping was explained by the transition from the dense crystalline structure of C 60 to the amorphous structure of the C 60 derivative. 7 The for mal potentials of redox transformations of fullerenes in the tetra(n octyl)ammonium bromide (TOAB) matrix were conf...

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Efficient 2 + 3 Cycloaddition Approach to Synthesis of Pyridinyl Based [60]Fullerene Ligands

Cited by 30 publications

References 10 publications

An Efficient [2+3] Cycloaddition Approach to the Synthesis of Pyridyl‐Appended Fullerene Ligands

An Efficient [2+3] Cycloaddition Approach to the Synthesis of Pyridyl‐Appended Fullerene Ligands

New pyrrolidine and pyrroline derivatives of fullerenes: from the synthesis to the use in light-converting systems

Structure of electroactive coatings based on fullerene and its derivatives

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