151872-44-5

Basic information

• Product Name: N-METHYLFULLEROPYRROLIDINE
• Synonyms: N-METHYLFULLEROPYRROLIDINE;MFP, MPC60, NMPC60;MPC60;NMPC60;N-Methylfulleropyrrolidine 99% (HPLC)
• CAS NO: 151872-44-5
• Molecular Formula: C₆₃H₇N
• Molecular Weight: 777.755
• Mol File: 151872-44-5.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: N-METHYLFULLEROPYRROLIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: N-METHYLFULLEROPYRROLIDINE(151872-44-5)
• EPA Substance Registry System: N-METHYLFULLEROPYRROLIDINE(151872-44-5)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 151872-44-5(Hazardous Substances Data)

Usage

Uses

Used in Electronics Industry:
N-METHYLFULLEROPYRROLIDINE is used as an electron acceptor for [application reason] in the development of organic solar cells and other electronic devices. Its ability to accept electrons makes it a valuable component in the creation of efficient energy transfer systems.
Used in Spectroscopy:
N-METHYLFULLEROPYRROLIDINE is used as a spectroscopic reference for [application reason] C60-based molecular heterojunctions. Its stable and well-defined properties make it an ideal reference point for studying the behavior of other molecules and materials in spectroscopic analyses.
Used in Redox Chemistry:
N-METHYLFULLEROPYRROLIDINE is used as a redox reference for [application reason] in redox reactions involving C60-based molecular heterojunctions. Its predictable and consistent behavior helps researchers understand the redox properties of other molecules and materials in the system.
Used in Energy Transfer Research:
N-METHYLFULLEROPYRROLIDINE is used as a study subject for [application reason] photoinduced energy and electron transfer between oligothienylenevinylenes and MP-C60. The detailed understanding of these processes can lead to advancements in the development of more efficient energy transfer systems and materials.

Upstream product

• 50-00-0 formaldehyd 
• 107-97-1 sarcosine 
• 99685-96-8 fullerene-C₆₀ 
• 75-50-3 trimethylamine 
• 267663-62-7 (+/-)-Diethyl 63-methyl-1,2-(methaniminomethano)-33,50-methano[60]fullerene-61,61-dicarboxylate 
• 555-16-8 4-nitrobenzaldehdye 
• 100-52-7 benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 100-10-7 4-dimethylamino-benzaldehyde 
• 708-76-9 2-hydroxy-4,6-dimethoxybenzaldehyde 
• 141-46-8 Glycolaldehyde 
• 75-57-0 tetramethlyammonium chloride 
• 108-88-3 toluene 

Relevant articles and documents

Preparation and Characterization of Six Bis(N-methylpyrrolidine)-C60 Isomers: Magnetic Deshielding in Isomeric Bisadducts of C60

A series isomers of bis(N-methylpyrrolidine)-C60 2 (prato bisdducts) was prepared by the 1,3-dipolar cycloaddition of N-methylazomethine ylide to C60.Six isomers were separated and characterized by ESI-MS, UV/vis, and 1H and 13C NMR spectroscopy.TThe structures of these bisadducts were assigned based on (1) comparison of their molecular symmetries with their 1H and 13C NMR spectra, (2) comparison of their UV/vis spectra with those of corresponding Bingel-Hirsch bisadducts, and (3) the order of deshielding of the methylene and N-methyl 1H NMR resonances.Prato bisaddition is less chemoselective than Bingel-Hirsch bisaddition to C60.

A New Dyad Based on C60 and a Conjugated Dimethylaniline-Substituted Dithienylethylene Donor

A facile synthesis of the title compound is described, and its optical and electrochemical properties are discussed.

Microwave-Assisted 1,3-Dipolar Cycloaddition of Azomethine Ylides to [60]Fullerene: Thermodynamic Control of Bis-Addition with Ionic Liquids Additives

The cycloaddition of azomethine ylides to [60]fullerene (C60) has been studied in ortho-dichlorobenzene (o-DCB) by evaluating the impact of an ionic liquid (IL) additive. The solvent effect has been addressed by evaluating the activation parameters of the cycloaddition and the boosting effect of the microwave (MW) induced dielectric heating. The IL additive plays a twofold role of stabilizing the dipolar ylide intermediate and favoring the retro-cycloaddition at high temperature regime. Under the conditions explored, a combined kinetic and thermodynamic preference favors the selective formation of trans bis-fulleropyrrolidine regioisomers, in agreement with the DFT computational analysis.

Investigation of the Photoelectrochemistry of C60 and Its Pyrrolidine Derivatives by Monolayer-Modified SnO2 Electrodes

A monolayer of a C60 mixture with arachidic acid (1:1) and C60-pyrrolidine derivatives were successfully obtained at the air/water interface and deposited onto solid substrates with tra

BOPHY-Fullerene C60 Dyad as a Photosensitizer for Antimicrobial Photodynamic Therapy

A novel BOPHY–fullerene C60 dyad (BP-C60) was designed as a heavy-atom-free photosensitizer (PS) with potential uses in photodynamic treatment and reactive oxygen species (ROS)-mediated applications. BP-C60 consists of a BOPHY fluorophore covalently attached to a C60 moiety through a pyrrolidine ring. The BOPHY core works as a visible-light-harvesting antenna, while the fullerene C60 subunit elicits the photodynamic action. This fluorophore–fullerene cycloadduct, obtained by a straightforward synthetic route, was fully characterized and compared with its individual counterparts. The restricted rotation around the single bond connecting the BOPHY and pyrrolidine moieties led to the formation of two atropisomers. Spectroscopic, electrochemical, and computational studies disclose an efficient photoinduced energy/electron transfer process from BOPHY to fullerene C60. Photodynamic studies indicate that BP-C60 produces ROS by both photomechanisms (type I and type II). Moreover, the dyad exhibits higher ROS production efficiency than its individual constitutional components. Preliminary screening of photodynamic inactivation on bacteria models (Staphylococcus aureus and Escherichia coli) demonstrated the ability of this dyad to be used as a heavy-atom-free PS. To the best of our knowledge, this is the first time that not only a BOPHY–fullerene C60 dyad is reported, but also that a BOPHY derivative is applied to photoinactivate microorganisms. This study lays the foundations for the development of new BOPHY-based PSs with plausible applications in the medical field.

A covalent organic cage compound acting as a supramolecular shadow mask for the regioselective functionalization of C60

A trigonal-bipyramidal covalent organic cage compound serves as an efficient host to form stable 1?:?1-complexes with C60 and C70. Fullerene encapsulation has been comprehensively studied by NMR and UV/Vis spectroscopy, mass spectrometry as well as single-crystal X-ray diffraction. Exohedral functionalization of encapsulated C60via threefold Prato reaction revealed high selectivity for the symmetry-matched all-trans-3 addition pattern. This journal is

Highly hydroxide conductive ionomers with fullerene functionalities

A novel ionomer was designed that will not poison the catalyst in alkaline fuel cells, by incorporating for the first time N-methyl pyrrolidine-C60 cation in polymeric anion exchange ionomers. The resultant fullerene-based anion exchange ionomer shows an extremely high hydroxide conductivity (182 mS cm-1) at a low cation concentration (0.62 mmol g-1).

Fullerene derivatives strongly inhibit HIV-1 replication by affecting virus maturation without impairing protease activity

Three compounds (1, 2, and 3) previously reported to inhibit HIV-1 replication and/or in vitro activity of reverse transcriptase were studied, but only fullerene derivatives 1 and 2 showed strong antiviral activity on the replication of HIV-1 in human CD4

Study on the thermal reactions of [60]fullerene with amino acids and amino acid esters

Thermal reactions of [60]fullerene with a series of amino acids and amino acid esters under aerobic and dark conditions have been investigated. Fulleropyrrolidines can be obtained from these reactions although an aldehyde is not added purposely. Possible reaction mechanisms involving uncommon C-N bond cleavages have been proposed to generate aldehydes, which then react with amino acids and amino acid esters to provide azomethine ylides, followed by 1,3-dipolar cycloaddition to [60]fullerene affording fulleropyrrolidines. Control experiments support our proposed mechanisms, and elucidate the innate nature of C-N bond cleavages of amino acids and amino acid esters.

H-bond-assisted regioselective (cis-1) intramolecular nucleophilic addition of the hydroxyl group to [60]fullerene

The one-step reaction of 2,6-dihydroxyphenylmethyl ketone and sarcosine with [60]fullerene in refluxing chlorobenzene affords, in a totally regioselective process, the cis-1 bicyclic-fused organofullerene through a new intramolecular nucleophilic addition