174278-68-3

Upstream product

• 107-97-1 sarcosine 
• 555-16-8 4-nitrobenzaldehdye 
• 99685-96-8 fullerene-C₆₀ 
• 100-14-1 4-nitrobenzyl chloride 

Downstream Products

• 266362-32-7 N-methyl-2-(4-aminophenyl)-bukminsterfulleropyrrolidine 

Relevant academic research and scientific papers

Preparation method of N-methyl-2-(4-nitrophenyl)-3,4-fulleropyrrolidine

A preparation method of N-methyl-2-(4-nitrophenyl)-3,4-fulleropyrrolidine comprises the following steps: (1) dissolving C60 powder into a non-polar solvent, thus obtaining a solution; (2) adding sarcosine and p-nitrobenzaldehyde into the solution obtained in the step (1), heating and refluxing; (3) cooling a mixed solution after completing reflux, and removing methylbenzene, thus obtaining a solid product; (4) eluting the solid product obtained in the step (3) by using a chromatographic column; (5) removing a solvent from a product solution obtained through eluting, washing and drying, thus obtaining a target product. The preparation method disclosed by the invention is simple, and the product is high in purity and high in yield.

Reactions of [60]fullerene with halides and amino acids to synthesize fulleropyrrolidines

The reactions of [60]fullerene with benzyl chlorides and amino acids in chlorobenzene (PhCl) were investigated. Fulleropyrrolidines bearing ArCH moieties originating from the corresponding benzyl chlorides through C-Cl bond cleavage were obtained from these reactions. Use of PhCl/DMSO instead of PhCl as the solvent significantly improved the reaction efficiency. A detailed investigation of these reactions resulted in the discovery of other halides - such as allyl chloride, methallyl chloride, cinnamyl chloride, propargyl bromide, ethyl bromoacetate, bromoacetonitrile, bromomethane, bromopropane and bromobutane - that could also react with [60]fullerene and amino acids to produce fulleropyrrolidines. This reaction could be an alternative to the Prato reaction for synthesizing fulleropyrrolidines when aldehydes are expensive or unavailable from commercial sources. A plausible reaction mechanism for product formation involving C-X bond cleavage in the halide to form the aldehyde is proposed.

Solvent-free reactions of fullerenes and N-alkylglycines with and without aldehydes under high-speed vibration milling

The solvent-free reactions of fullerenes and N-alkylglycines with and without aldehydes (RCHO) 2a-e under high-speed vibration milling (HSVM) conditions have been investigated. Fulleropyrrolidines 4a-e (C60(CH2N(CH3)CHR), R=H (4a), C6H5 (4b), p-NO2-C6H4 (4c), p-CH3O-C6H4 (4d), p-(CH3)2N-C6H4 (4e)) were obtained in moderate yields from reactions of C60 with aldehydes 2a-e and N-methylglycine (Prato reaction). In all these solvent-free reactions, 4a was found to be formed besides 4b-e, indicating that fullerenes can react with N-substituted glycines in the absence of aldehyde to give fulleropyrrolidines. For this novel reaction, a possible reaction mechanism involving an electron transfer process has been proposed. Intrigued by this observation, the dependence of the yield on the reagent ratio for the reaction of C60 with paraformaldehyde and/or N-methylglycine was examined to search the optimal conditions. The reaction of C70 with paraformaldehyde and/or N-methylglycine under HSVM conditions was also studied and was found to give the positional isomers of [70]fulleropyrrolidines.

Synthesis of novel nitroso-fulleropyrrolidines

Novel fulleropyrrolidines containing differently head groups (-NO2, -NH2 -NO) spaced by a long chain from the fulleropyrrolidine moiety have been synthesised and characterised.

Linear free-energy relationship for electron-transfer processes of pyrrolidinofullerenes with tetrakis(dimethylamino)ethylene in ground and excited states

Systematic studies of electron-transfer processes in the ground states and excited triplet states of pyrrolidinofullerenes {C60(C3H6N)R [R = H (1), p-C6H4NO2 (2), p-C6H4CHO (3), p-C6H5 (4), p-C6H4Me (5), p- C6H4NMe2 (6)]} with tetrakis(dimethylamino)ethylene (TDAE) have been carried out by steady-state and transient absorption measurements in the visible-NIR region. Analyses of the equilibria of the electron-transfer processes in the ground states indicate that free ion radicals are produced in polar solvents. Photoinduced electron-transfer processes via (T)(C60(C3H6N)R)* were observed by applying a perturbation to the equilibria of the electron-transfer reactions in the ground states by laser flash photolysis. Based on the relationship of the thermodynamic data and kinetic data, the electron-transfer rate constants in the ground states (k(et)/(G)) can be evaluated. The k(et)/(G) values are affected by the substituents to a smaller extent compared with the equilibrium constants (K) in polar solvents; α = 0.6 in Δ log k(et)/(G) = α Δ log K. This α value indicates that the activation energies of forward electron transfer in the ground states vary moderately with the thermodynamic stabilities of (C60(C3H6N)R).-. Electron-transfer rate constants via (T)(C60(C3H6N)R)* which are close to the diffusion-controlled limit, do not show a large substituent effect (α = 0), because of their highly exothermic processes. Such a linear free-energy relationship can be extended to other systems such as (T)(C60(C3H6N)R)*/N,N-dimethylaniline, from which valuable information for electron-transfer processes can be obtained.