Buckminsterfullerene

Base Information

• Chemical Name: Buckminsterfullerene
• CAS No.: 99685-96-8
• Molecular Formula: C₆₀
• Molecular Weight: 720.66
• Hs Code.: 28030000
• European Community (EC) Number: 628-630-7
• UNII: NP9U26B839
• DSSTox Substance ID: DTXSID4031772
• Wikipedia: Buckminsterfullerene
• Wikidata: Q1075376
• Mol file: 99685-96-8.mol

Synonyms:Buckminsterfullerene;Buckminsterfullerenes;Buckyball;Buckyballs;Fullerene;Fullerenes

Chemical Property of Buckminsterfullerene

Chemical Property:

• Appearance/Colour: black to brown crystalline powder
• Melting Point: >280 °C(lit.)
• Refractive Index: 1.813
• Boiling Point: 500-600℃ subl.
• Flash Point: 94 °C
• PSA: 0.00000
• Density: 3.43 g/cm³
• LogP: 17.73000
• Storage Temp.: Dark Room
• Solubility.: organic solvents: soluble
• Water Solubility.: Soluble in toluene. Insoluble in water.
• XLogP3: 16.4
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 0
• Rotatable Bond Count: 0
• Exact Mass: 720
• Heavy Atom Count: 60
• Complexity: 2030

Purity/Quality:

99% up by HPLC ^*data from raw suppliers

Fullerene C60 ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37
• Safety Statements: 26-36

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Other Classes -> Other Organic Compounds
• Canonical SMILES: C12=C3C4=C5C6=C1C7=C8C9=C1C%10=C%11C(=C29)C3=C2C3=C4C4=C5C5=C9C6=C7C6=C7C8=C1C1=C8C%10=C%10C%11=C2C2=C3C3=C4C4=C5C5=C%11C%12=C(C6=C95)C7=C1C1=C%12C5=C%11C4=C3C3=C5C(=C81)C%10=C23
• Description: Fullerenes are molecules that composed entirely of carbon. They are similar in structure to graphite, which is composed of a sheet of linked hexagonal and pentagonal rings that prevent the sheet from being planar. Each carbon atom on the surface of fullerenes is bonded to three carbon neighbors, therefore, is sp2 hybridized. Fullerenes are in the form of a hollow sphere, ellipsoid, tube, and many other shapes.? Spherical fullerenes C60, the first fullerene molecule manufactured in 1985, is named as buckminsterfullerene, resembles the balls used in football. Cylindrical fullerenes are known as carbon nanotubes (CNTs). As the discovery of fullerenes came after buckminsterfullerene, the shortened name “fullerene” is used to refer to the family of fullerenes, of which each carbon atom is covalently bonded to three others. The most specific feature of fullerenes is that they are excellent electron acceptors (n-type semiconductors), which are suitable for organic electronic materials with electron carriers. Fullerenes can be used to fabricate polymer/fullerene blend for organic photovoltaics, in which fullerene acts as the n-type semiconductor. Fullerenes are powerful antioxidants, which react readily and at a high rate with free radicals. These free radicals usually lead to cell damage or death. Therefore, fullerenes show great promise in health and personal care applications, in which the prevention of oxidative cell damage or death is desirable. Fullerenes are also used in non-physiological applications, where oxidation and radical processes are destructive (food spoilage, plastics deterioration, metal corrosion). Research interests on fullerenes include also the use of fullerenes to control the neurological damage of diseases such as Alzheimer’s disease and Lou Gehrig’s disease. Fullerenes are used as additives for polymers to create copolymers or composites with specific physical and mechanical properties. Fullerenes can be doped with rubidium and cesium to fabricate superconductors with electron carriers, of which the superconducting transitions occur at more than 30 K. C60, [60]Fullerene is a molecule with prominent electron acceptor property composed of 60 carbons in the shape of a hollow football with 20 hexagons and 12 pentagons. Fullerene is unsaturated, each carbon connecting to 3 other carbons instead of 4 with fused 5 and 6 membered rings.
• Uses: High purity carbon 60 fullerenes for use in thermal evaporation systems as either electron acceptors, n-type semiconductors or interface layers. Fullerene powder is useful for biomedical applications such as the design of high-performance MRI contrast agents, x-ray imaging contrast agents and photodynamic therapy. It is also essential for single-walled carbon nanotubes with narrow diameter-distribution. It is used as light-activated antimicrobial agent. It also finds application in the field of nanotechnology, heat resistance and superconductivity.

Technology Process of Buckminsterfullerene

There total 140 articles about Buckminsterfullerene which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 68.0%

C60*C106H92Ag2N4O12(2+)*2NO3(1-) → C53H46N2O6 (1450830-80-4) + silver (7440-22-4) + fullerene-C60 (99685-96-8,161105-99-3,161106-00-9,111138-12-6,133318-63-5,134053-11-5,134931-35-4,134931-36-5,139703-76-7,145633-27-8,175414-73-0,175414-74-1,175414-75-2,175519-12-7,175519-13-8,175519-14-9,175519-15-0,136376-46-0,144906-37-6,144906-38-7,151767-00-9,152882-97-8,152882-98-9,152882-99-0,153062-34-1,154171-74-1,154171-75-2,154333-99-0,154334-00-6,154397-63-4,154460-59-0,199456-56-9,108739-25-9,120329-57-9,120329-58-0)

Guidance literature:

In acetonitrile; at 20 ℃; for 1.5h; Irradiation;

DOI:10.1021/ja406893y

Reference yield: 41.0%

C74H11N3O3 (1016894-31-7) → ethyl 4-nitrobenzoate (99-77-4) + fullerene-C60 (99685-96-8,161105-99-3,161106-00-9,111138-12-6,133318-63-5,134053-11-5,134931-35-4,134931-36-5,139703-76-7,145633-27-8,175414-73-0,175414-74-1,175414-75-2,175519-12-7,175519-13-8,175519-14-9,175519-15-0,136376-46-0,144906-37-6,144906-38-7,151767-00-9,152882-97-8,152882-98-9,152882-99-0,153062-34-1,154171-74-1,154171-75-2,154333-99-0,154334-00-6,154397-63-4,154460-59-0,199456-56-9,108739-25-9,120329-57-9,120329-58-0) + 1,2-epox-[60]fullerene (148347-18-6,139141-81-4)

Guidance literature:

With maleic anhydride; In toluene; at 20 ℃; for 1h; Solvent; Inert atmosphere; Irradiation;

DOI:10.1039/c4cc03859b

Reference yield: 13.3%

graphite → fullerene-C60 (99685-96-8,161105-99-3,161106-00-9,111138-12-6,133318-63-5,134053-11-5,134931-35-4,134931-36-5,139703-76-7,145633-27-8,175414-73-0,175414-74-1,175414-75-2,175519-12-7,175519-13-8,175519-14-9,175519-15-0,136376-46-0,144906-37-6,144906-38-7,151767-00-9,152882-97-8,152882-98-9,152882-99-0,153062-34-1,154171-74-1,154171-75-2,154333-99-0,154334-00-6,154397-63-4,154460-59-0,199456-56-9,108739-25-9,120329-57-9,120329-58-0) + [5,6]fullerene-C70 (741268-81-5,741268-84-8,133227-82-4,133320-10-2,133320-11-3,133869-47-3,134054-62-9,134932-61-9,149820-05-3,149820-06-4,157903-26-9,175779-21-2,115383-22-7,958017-68-0,958017-71-5,958017-74-8,958017-77-1,958017-80-6,140630-87-1,140694-21-9,151716-50-6,157008-89-4,220062-79-3,220062-83-9)

Guidance literature:

With tetrachloromethane; In gaseous matrix; Electric Arc; arc-discharge react. in He (300 Torr) with addn. of CCl4 (10 Torr); reverse phase liq. chromy. and UV spect.;

DOI:10.1039/b306921b

upstream raw materials:

PERYLENE

3'-[4-(phenylmethoxy)phenyl][5,6]fullereno-C₆₀-I_h-[1,9-d]isoxazole

Downstream raw materials:

ethyl 3′H-cyclopropa[1,9](C₆₀-I_h)[5,6]fullerene-3′-carboxylate

1-(dimethylphenylsilylmethyl)-1,9-dihydro(C₆₀-I_h)[5,6]fullerene

methyl (6,7)-[6,6]-C₆₀-fullerene-(5,8)-dihydronapthyl-2-formic acid ester

Refernces

• 1、 Ma, Wan,Wang, Kun,Huang, Cheng,Wang, Hui-Juan,Li, Fa-Bao,Sun, Rui,Liu, Li,Liu, Chao-Yang,Asiri, Abdullah M.. "Stereoselective synthesis of amino-substituted cyclopentafullerenes promoted by magnesium perchlorate/ferric perchlorate". supporting information. p. 964 - 974. Retrieved 2020/02/15.
• 2、 Peng, Jie,Xiang, Jun-Jun,Wang, Hui-Juan,Li, Fa-Bao,Huang, Yong-Shun,Liu, Li,Liu, Chao-Yang,Asiri, Abdullah M.,Alamry, Khalid A.. "DMAP-Mediated Synthesis of Fulleropyrrolines: Reaction of [60]Fullerene with Aromatic Aldehydes and Arylmethanamines in the Absence or Presence of Manganese(III) Acetate". . p. 9751 - 9764. Retrieved 2017/09/22.