174278-70-7

Basic information

• Product Name: 1-methyl-2-phenyl[60]fullereno[c]pyrrolidine
• Synonyms: 1-methyl-2-phenyl[60]fullereno[c]pyrrolidine
• CAS NO: 174278-70-7
• Molecular Weight: 853.853
• Mol File: 174278-70-7.mol

Chemical Properties

• CAS DataBase Reference: 1-methyl-2-phenyl[60]fullereno[c]pyrrolidine(CAS DataBase Reference)
• NIST Chemistry Reference: 1-methyl-2-phenyl[60]fullereno[c]pyrrolidine(174278-70-7)
• EPA Substance Registry System: 1-methyl-2-phenyl[60]fullereno[c]pyrrolidine(174278-70-7)

Safety Data

• Hazardous Substances Data: 174278-70-7(Hazardous Substances Data)

Upstream product

• 107-97-1 sarcosine 
• 100-52-7 benzaldehyde 
• 99685-96-8 fullerene-C₆₀ 
• 100-44-7 benzyl chloride 
• 50-00-0 formaldehyd 
• 103-67-3 benzyl-methyl-amine 
• 75-57-0 tetramethlyammonium chloride 
• 108-88-3 toluene 
• 1112-67-0 tetrabutyl-ammonium chloride 
• 56-34-8 tetraethylammonium chloride 

Relevant articles and documents

Metal-Free Synthesis of N-Alkyl-2,5-Unsubstituted/Monosubstituted Fulleropyrrolidines: Reaction of [60]Fullerene with Paraformaldehyde and Amines

A series of scarce N-alkyl-2,5-unsubstituted/monosubstituted fulleropyrrolidines were synthesized in moderate to excellent yields by the simple one-step thermal reaction of [60]fullerene with primary/secondary amines in the presence of paraformaldehyde without the addition of valuable metal salts. Intriguingly, the reaction with primary amines unexpectedly afforded N-alkyl-2,5-unsubstituted fulleropyrrolidines instead of the anticipated 2,5-monosubstituted fulleropyrrolidines. A plausible reaction pathway is proposed to elucidate the above-mentioned reaction process based on the experimental results.

Cymantrenyl and styryl derivatives of 1-methyl[60]fullereno[c]pyrrolidine: Synthesis and electrochemical behavior

New cymantrenyl derivatives of 1-methyl[60]fullereno[c]pyrrolidine were obtained. According to electrochemical data, the cymantrenyl and phenyl fragments show close electron-donating effects in the presence of the strong acceptor fullerene.

Excitation-dependent electron exchange energy and electron transfer dynamics in a series of covalently tethered: N, N-bis(4′-tert-butylbiphenyl-4-yl)aniline-[C60] fullerene dyads via varying π-conjugated spacers

Femtosecond time-resolved fluorescence and transient absorption studies are reported for three newly synthesized covalently linked N,N-bis(4′-Tert-butylbiphenyl-4-yl)aniline (BBA) and pyrrolidinofullerenes (C60)-based donor-π conjugated bridge-Acceptor dyads (D-B-A) as functions of the bridge length (7.1, 9.5 and 11.2 ? for Dyad-1, Dyad-2 and Dyad-3), dielectric constants of the medium and pump wavelengths. In polar solvent, ultrafast fluorescence quenching (kEET ≥ 2 × 1012 s-1) of the BBA moiety upon excitation of the BBA moiety (320 nm) is observed in the dyads and is assigned to a mechanism involving electron exchange energy transfer (EET) from 1BBA? to C60 followed by electron transfer from BBA to 1C60?. Cohesive rise and decay dynamics of conjugated BBA+-C60- anion pairs confirm the involvement of a distance independent adiabatic charge-separation (CS) process (kCS ≥ 2.2 × 1011 s-1) with near unity quantum efficiency (φCS ≥ 99.7%) and a distance-dependent non-Adiabatic charge-recombination (CR) process [kCR ～ (1010-108) s-1]. In contrast, excitation of the C60 moiety (λex = 430 to 700 nm) illustrates photoinduced electron transfer from BBA to 1C60?, involving non-Adiabatic (diabatic) and distance-dependent CS (kCS in the range of 0.59-1.78 × 1011 s-1) with 98.86-99.6% (Dyad-3-Dyad-1) quantum efficiency and a CR process with kCR values [kCR ～ (1010-108) s-1] up to three orders greater than kCS of the respective dyads. Both the processes, CS and CR, upon C60 excitation and the CR process upon BBA excitation show distance dependent rate constants with exponential factor β ≤ 0.5 ?-1, and electron transfer is concluded to occur through a covalently linked conjugated π bridge. Global and target analysis of fsTA data reveal the occurrence of two closely lying CS states, thermally hot (CShot) and thermally relaxed (CSeq) states, and two CR processes with two orders of different rate constants. Careful analysis of the kinetic and thermodynamic data allowed us to estimate the total reorganization energy and electronic coupling matrix (V), which decrease exponentially with distance. These novel features of the distance independent adiabatic CS process and the distance-dependent diabatic CR process upon donor excitation are due to extending the π-conjugation between BBA and C60. The demonstrated results may provide a benchmark in the design of light-harvesting molecular devices where ultrafast CS processes and long-lived CS states are essential requirements.

A micron tree leafshaped structural N-methyl-2-phenyl -3,4-fullerenols alkenyl pyrrolidine preparation method and application

The invention relates to a preparation method and an application of N-methyl-2-phenyl-3,4-fulleropyrrolidine of a micron leaf structure. The preparation method is used for preparing the N-methyl-2-phenyl-3,4-fulleropyrrolidine and the N-methyl-2-phenyl-3,4-fulleropyrrolidine of the micron leaf structure by using fullerene C60, benzaldehyde and sarcosine as raw materials, and the N-methyl-2-phenyl-3,4-fulleropyrrolidine of the micron leaf structure is used as a carrier and used for preparing a catalyst for producing p-aminophenol from nitrobenzene through catalytic hydrogenation. The product of the method for producing the N-methyl-2-phenyl-3,4-fulleropyrrolidine is high in yield and purity, and the prepared catalyst is high in activity and long in service life.

Fullerene derivatives with increased dielectric constants

The invention of new organic materials with high dielectric constants is of extreme importance for the development of organic-based devices such as organic solar cells. We report on a synthetic way to increase the dielectric constant of fullerene derivati

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.

Flowerlike supramolecular architectures assembled from C60 equipped with a pyridine substituent

Fullerene (C60)-rich and photoconductive flowerlike supramolecular assembly was constructed from self-organization of pyridine substituted C60 by a facile drop-casting method. The Royal Society of Chemistry 2010.

Synthesis of fulleropyrrolidines through the reaction of [60]fullerene with quaternary ammonium salts and amino acids

The reactions of [60]fullerene with amino acids and quaternary ammonium salts in toluene afforded two fulleropyrrolidine derivatives. One fulleropyrrolidine derivative contained a RCH moiety originating from quaternary ammonium salts through C-N bond cleavages and other fulleropyrrolidine derivatives contained a PhCH moiety originating from toluene through C-H bond cleavage. By using chlorobenzene instead of toluene as solvent, only one fulleropyrrolidine derivative containing a RCH moiety was obtained in the reactions.

A glycyl-substituted porphyrin as a starting compound for the synthesis of a π-π-stacked porphyrin-fullerene dyad with a frozen geometry

A synthetic route for obtaining a porphyrin-fullerene dyad with a constrained geometry forcing the [60]fullerene sphere to lie on the porphyrin plane is reported, revealing a strong interaction in the ground state between the two chromophores. The Royal S

Synthesis of perylene-3,4-mono(dicarboximide)-fullerene C60 dyads as new light-harvesting systems

(Graph Presented) Fullerene C60-perylene-3,4-mono(dicarboximide) (C60-PMI) dyads 1-3 were synthesized in the search for new light-harvesting systems. The synthetic strategy to the PMI intermediate used a cross-coupling Suzuki reaction for the introduction of a formyl group in the ortho, meta, or para position. Subsequent 1,3-dipolar cycloaddition with C 60 led to the target C60-PMI dyad. Cyclic voltammetry showed that the first one-electron reduction process unambiguously occurs onto the C60 moiety and the following two-electron process corresponds to the concomitant second reduction of C60 and the first reduction of PMI. A quasi-quantitative quenching of fluorescence was shown in dyads 1-3, and an intramolecular energy transfer was suggested to occur from the PMI to the fullerene moiety. These C60-PMI dyads constitute good candidates for future photovoltaic applications with expected well-defined roles for both partners, i.e., PMI acting as a light-harvesting antenna and C60 playing the role of the acceptor in the photoactive layer.