115383-22-7

Basic information

• Product Name: Fullerene C70
• Synonyms: FULLERENE, C60/C70;FULLERENE;FULLERENES, C60/C70;FULLERENES C60/C70 MIXTURE;FULLERENES MIXTURE, C-60 AND C-70;FULLERENE NANOTUBE;FULLERENE PRECURSOR;FULLERITE
• CAS NO: 115383-22-7
• Molecular Formula: C₇₀
• Molecular Weight: 840.749
• Product Categories: C60 & C70;Functional Materials;metal or element;OLED
• Mol File: 115383-22-7.mol

Chemical Properties

• Melting Point: >280 °C(lit.)
• Boiling Point: 500-600℃ subl.
• Appearance: black/powder
• Density: ca 1.7
• Storage Temp.: Dark Room
• Solubility: benzene: soluble
• Water Solubility: Soluble in benzene and toluene. Insoluble in water.
• CAS DataBase Reference: Fullerene C70(CAS DataBase Reference)
• NIST Chemistry Reference: Fullerene C70(115383-22-7)
• EPA Substance Registry System: Fullerene C70(115383-22-7)

Safety Data

• Hazard Codes: Xi
• Statements: 36/37-36/37/38
• Safety Statements: 26-36-24/25-22
• RIDADR: UN1325
• WGK Germany: 3
• HazardClass: 4.1
• PackingGroup: III
• Hazardous Substances Data: 115383-22-7(Hazardous Substances Data)

Usage

Uses

Used in Thermal Evaporation Systems:
Fullerene C70 is used as a material in thermal evaporation systems for its increased optical absorption properties, enhancing energy efficiency.
Used in Chemical Research:
Fullerene C70 is used as a research material in chemical research, providing insights into the unique properties and potential applications of fullerene compounds.
Used in Biomedical Applications:
Fullerene C70 is used as a component in the design of high-performance MRI contrast agents, X-Ray imaging contrast agents, photodynamic therapy, and drug and gene delivery systems, due to its unique chemical and physical properties.
Used in Energy Efficiency:
Fullerene C70 is used in products that have been enhanced for energy efficiency, contributing to the development of more sustainable and efficient technologies.

Purification Methods

It was purified from the soluble toluene extract (400mg) of the soot (Fullerite) formed from resistive heating of graphite by adsorption on neutral alumina (100g, Brockmann I, 60 x 8cm). Elution with toluene/hexane (5:95 v/v) gives ca 250mg of quite pure C6 0. It has characteristic spectral properties (see below). Further elution with toluene/hexane (20:80 v/v, i.e. increased polarity of solvent) provides 50mg of "pure" C7 0 [Allemand et al. J Am Chem Soc 113 1050 1991]. Chromatography on alumina can be improved by using conditions which favour adsorption rather than crystallisation. Thus the residue from toluene extraction (1g) in CS2 (ca 300mL) is adsorbed on alumina (375g, standard grade, neutral ca 150 mesh, Brockmann I) and loaded as a slurry in toluene/hexanes (5:95 v/v) to a 50 x 8cm column of alumina (1.5Kg) in the same solvent. To avoid crystallisation of the fullerenes, 10% of toluene in hexane is added quickly followed by 5% of toluene in hexane after the fullerenes had left the loading fraction (2-3hours). With a flow rate of 15mL/minute the purple C6 0 fraction is eluted during a 3-4hour period. Evaporation of the eluates gives 550-630mg of product which, after recrystallisation from CS2/cyclohexane yields 520-600mg of C60 which contains adsorbed solvent. On drying at 275o/10-3mm for 48hours a 2% weight loss is observed although the C60 still contains traces of solvent. Further elution of the column with 20% of toluene in hexane provides 130mg of C7 0 containing 10-14% of C60 (by NMR). This was rechromatographed as above using a half scale column and adsorbing the 130mg in CS2 (20mL) on alumina (24g) and gave 105mg of recrystallised C7 0 (containing 2% of C6 0). The purity of C6 0 can be improved further by washing the crystalline product with Et2O and Me2CO followed by recrystallisation from *C6H6 and vacuum drying at high temperatures. Carbon soot from resistive heating of a carbon rod in a partial helium atmosphere (0.3bar) under specified conditions is extracted with boiling *C6H6 or toluene, filtered and the red-brown solution is evaporated to give crystalline material in 14% yield which is mainly a mixture of fullerenes C6 0 and C7 0. Chromatographic filtration of the 'crude' mixture with *C6H6 allows no separation of components, but some separation was observed on silica gel TLC with n-hexane or n-pentane, but not cyclohexane as eluents. Analytical HPLC with hexanes (5_m Econosphere silica) gave satisfactory separation of C6 0 and C7 0 (retention times of 6.64 and 6.93minutes respectively) at a flow rate of 0.5mL/minute and using a detector at 256nm. HPLC indicated the presence of minor (<1.5% of total mass) unidentified Cn species with retention times of 5.86 and 8.31minutes. Column chromatography on flash silica gel with hexane gives a few fractions of C6 0 with
95% purity, but later fractions contain mixtures of C6 0 and C7 0. These can be obtained in 99.85 and >99% purity, respectively, by column chromatography on neutral alumina. [Ajie et al. J Phys Chem 94 8630 1990.] Separation of C60 and C7 0 can be achieved by HPLC on a dinitroanilinopropyl (DNAP) silica (5_m pore size, 300. pore diameter) column with a gradient from n-hexane to 50% CH2Cl2 using a diode array detector at wavelengths 330nm (for C6 0) and 384nm (for C7 0). [Cox et al. J Am Chem Soc 113, 2940, 1991.] Soxhlet extraction of the "soot" is a good preliminary procedure, or if material of only ca 98% purity is required. Soxhlet extraction with toluene is run (20 minutes per cycle) until colourless solvent filled the upper part of the Soxhlet equipment (10 hours). One-third of the toluene remained in the pot. After cooling, the solution was filtered through a glass frit. This solid (purple in toluene) was ca 98% C6 0. This powder was again extracted in a Soxhlet using identical conditions as before, and the C60 was recrystallised from toluene to give 99.5% pure C60. C70 has greater affinity than C6 0 for toluene. [Coustel et al. J Chem Soc, Chem Commun 1402 1992.] Purification of C60 from a C60/C70 mixture was also achieved by dissolving it in an aqueous solution of (but not ) cyclodextrin (0.02M) upon refluxing. The rate of dissolution (as can be followed by the UV spectra) is quite slow and constant up to 10-5M of C60. The highest concentration of C60 in H2O obtained was 8 x 10-5M and a 2 cyclodextrin:1 C60 clathrate is obtained. C60 is extracted from this aqueous solution by toluene and C60 of >99 purity is obtained by evaporation. With excess of cyclodextrin more C6 0 dissolves and the complex precipitates. The precipitate is insoluble in cold H2O but soluble in boiling H2O to give a yellow solution. [Andersson et al. J Chem Soc, Chem Commun 604 1992.] C60 and C70 can also be readily purified by inclusion complexes with p-tert-butylcalix[6] and [8]arenes. Fresh carbon-arc soot (7.5g) is stirred with toluene (250mL) for 1hour and filtered. To the filtrate is added p-tertbutylcalix[ 8]arene, refluxed for 10minutes and filtered. The filtrate is seeded and set aside overnight at 20o. The C60 complex separates as yellow-brown plates and is recrystallised twice from toluene (1g from 80mL) to give a 90% yield. Addition of CHCl3 (5mL) to the complex (0.85g) gave C60 (0,28g, 92% from recrystallised complex). p-tert-Butylcalix[6]arene-(C60)2 complex is prepared by adding p-tert-butylcalix[6]arene (4.4mg) to a refluxing solution of C60 (5mg) in toluene (5mL). The hot solution is filtered rapidly and cooled overnight to give prisms (5.5mg, 77% yield). Pure C60 is obtained by decomposing the complex with CHCl3 as above. The p-tert-butylcalix[6]arene-(C70)2 complex is obtained by adding p-tert-butylcalix[6]arene (5.8mg) to a refluxing solution of C70 (5mg) in toluene (2mL), filtering hot and slowly cooling to give red-brown needles (2.5mg, 31% yield) of the complex. Pure C7 0 is then recovered by decomposing the complex with CHCl3. Decomposition of these complexes can also be achieved by boiling a toluene solution over KOH pellets for ca 10minutes. The calixarenes form Na salts which do not complex with the fullerenes. These appear to be the most satisfactory means at present for preparing large quantities of relatively pure fullerene C60 and C70 and is considerably cheaper than previous methods. [Atwood et al. Nature 368 229 1994.] Repeated chromatography on neutral alumina yields minor quantities of solid samples of C76, C84, C90 and C94 believed to be higher fullerenes. A stable oxide C70 has been identified. These have been separated by repeated flash chromatography on alumina with gradient elution using hexane/toluene mixtures (starting from 95:5 and increasing proportions of toluene until the ratio of 50:50 was attained) [Diederich et al. Science 2 5 2 548 1991].

InChI:InChI=1/C70/c1-2-22-5-6-24-13-14-26-11-9-23-4-3(21(1)51-52(22)54(24)55(26)53(23)51)33-31(1)61-35-7-8-27-15-16-29-19-20-30-18-17-28-12-10(25(7)56-57(27)59(29)60(30)58(28)56)37(35)63(33)65-36(4)40(9)67(44(17)42(12)65)69-46(11)47(14)70(50(20)49(18)69)68-43(13)39(6)66(45(16)48(19)68)64-34(5)32(2)62(61)38(8)41(15)64

Upstream product

• 170503-87-4 (+/-)-tetraethyl 1,2:56,57-bis(methano)<70>fullerene-71,71,72,72-tetracarboxylate 
• 170503-86-3 (+/-)-tetraethyl 1,2:67,68-bis(methano)<70>fullerene-71,71,72,72-tetracarboxylate 
• 170503-88-5 tetraethyl 1,2:41,58-bis(methano)<70>fullerene-71,71,72,72-tetracarboxylate 
• 153218-95-2 C₇₇H₁₀O₄ 
• 100-39-0 benzyl bromide 
• 144240-52-8 1,2-C₇₀H₂ 
• 7440-05-3 palladium 
• 67-66-3 chloroform 
• 106-99-0 buta-1,3-diene 
• 1120395-94-9 3,8,13-tribromo-5,10,15-tris-naphthalen-2-ylmethylene-10,15-dihydro-5H-diindeno[1,2-a:1',2'-c]fluorene 
• 7440-44-0 pyrographite 
• 187737-37-7 propene 
• 141197-61-7 [76]fullerene 
• 177904-73-3 penta(cyclopentadienyl)-η(5)-cyclopentadienylmanganesetricarbonyl 

Downstream Products

• 581-80-6 4,4'-bis(trifluoromethyl)biphenyl 
• 244237-40-9 2,5,10-triphenyl-2,5,6,10-tetrahydro[70]fullerene 
• 319016-52-9 [mer-W(CO)3(1,1'-bis(diphenylphosphino)ferrocene)](η(2)-C70) 

Relevant articles and documents

Structure and properties of the Fullerene Dimer C140 produced by pressure treatment of C70

A [2+2] cycloaddition cap-to-cap C70 dimer with C2h, molecular symmetry was synthesized in high yield by pressure treatment of polycrystalline C70 at 1 GPa and 200 °C. It was separated from unreacted monomers by chromatography and characterized by 13C NMR, Raman, and infrared spectroscopy, and other methods. Remarkably, only one isomer was produced out of the five possible [2+2] cycloaddition products which have equally low formation energies according to semiempirical modeling calculations. The dimer obtained is the one favored when C70 molecules adopt an ordered packing with parallel D5 axes. The intercage bonding in C140, its thermal stability, and intercage vibrational modes are similar to those found for the C60 dimer, C120. Both dimers photodissociate to the monomers in solution, probably via excited triplet states. The UV absorption and fluorescence properties of C140 are not very different from those of C70, suggesting only weak electronic interactions between the two cages of C140. In comparison, the pressure-induced dimerization of C60, under the conditions used for C70, results mainly in C60 oligomers and polymeric chains, but the dimer C120 could be isolated at low yield when short reaction times (≤5 min) were used.

Electron Transfer from Tetrathiafulvalenes to Photoexcited C70 Studied by Observing Transient Absorption in the Near-IR Region

The photoinduced electron transfer between C70 and tetrathiafulvalene or bis(ethylenedithio)tetrathiafulvalene in polar and nonpolar solvents and their mixture has been investigated by nanosecond laser photolysis/transient absorption spectroscopy in the visible and near-IR regions.The transient absorption bands of the triplet state of C70 observed in polar solvents decayed upon addition of tetrathiafulvalenes accompanied by the appearance of the transient absorption bands of the radical anion of C70.In benzene, the quenching of the triplet state of C70 was observed without the appearance of the radical anion of C70 within a nanosecond laser pulse, suggesting a collisional quenching of the triplet state of C70 with tetrathiafulvalenes.The quantum yield for the formation of the radical anion via the triplet state of C70 was about 1 for tetrathiafulvalene in benzonitrile.The quantum yield decreased in less polar solvents.The back electron transfer rates were also evaluated in polar solvents.

The chemical retro-Bingel reaction: Selective removal of bis(alkoxycarbonyl)methano addends from C60 and C70 with amalgamated magnesium

Bis(alkoxycarbonyl)methano addends are removed from C60 and C70 derivatives by reaction with amalgamated magnesium in dry THF; this facile and selective retro-Bingel reaction, which leaves pyrrolidine rings fused to C60 intact, opens up the possibility of using bis(alkoxycarbonyl)methano addends as protecting and reversible directing groups in the regioselective multiple functionalization of fullerenes.

Retro-cycloaddition reaction of pyrrolidinofullerenes

(Chemical Equation Presented) All things retro: Pyrrolidinofullerenes undergo a retro-cycloaddition reaction to afford the corresponding fullerene (C60, C70, or an endohedral C80 metallofullerene; see scheme) in quantitative yield upon treatment with an excess of a dipolarophile (maleic anhydride or N-phenyl-maleimide) in o-dichlorobenzene. The reaction works efficiently with higher fullerenes and has allowed the isolation of one of the constitutional isomers of Sc 3N@C80.

Unimolecular dissociations of C70+ and its noble gas endohedral cations Ne@C70+ and Ar@C70 +: Cage-binding energies for C2 loss

The energetics and dynamics of unimolecular decompositions of C 70+ and its noble gas endohedral cations, Ne@C 70+ and Ar@C70+, have been studied using tandem mass spectrometry techniques. The high-resolution mass-analyzed ion kinetic energy (HR-MIKE) spectra for the unimolecular reactions of C 70+, Ne@C70+, and Ar@C 70+ were recorded by scanning the electrostatic analyzer and using single-ion counting that was achieved by combination of an electron multiplier, amplifier/discriminator, and multichannel analyzer. These cations dissociate unimolecularly via loss of a C2 unit, and no endohedral atom is observed as fragment. The activation energies for C2 evaporation from Ne@C70+ and Ar@C70+ are lower than those for elimination of the endohedral noble gas atoms. The kinetic energy release distributions (KERDs) for the C2 evaporation have been measured and, by use of the finite heat bath theory (FHBT), the binding energies for the C2 emission have been deduced from the KERDs. The C2 evaporation energies increase in the order ΔEvap(C70+) vap(Ne@C70+) vap(Ar@C70+), but no big difference in the cage binding was observed for C70+, Ne@C70 +, and Ar@C70+, indicating incorporations of the Ne and Ar atoms into C70 contribute a little to the stability of C70 toward C2 loss, which is in good agreement with theoretical calculations but contrasts with the findings in their C60 analogues and in metallofullerenes that the decay energies of the filled fullerenes are much higher than those of the corresponding empty cages.

Radical reaction of C70Cl10 with P(OEt)3: Isolation and characterization of C70[P(O)(OEt)2] nHn (n = 1, 2)

The Arbuzov-type reaction of chlorofullerene C70Cl10 with P(OEt)3 leads to the formation of C70[P(O)(OEt) 2]H and C70[P(O)(OEt)2]2H 2, whose molecular struc

Self-crystallization of C70 cubes and remarkable enhancement of photoluminescence

Good solvent, poor solvent: A simple precipitation method enabled the spontaneous formation of homogeneous C70 cube crystals by self-crystallization in cavities of a good solvent (mesitylene) surrounded by a poor solvent (isopropyl alcohol, IPA; see picture). The enormously increased photoluminescence (PL) intensity of the C70 cube crystals relative to that of C70 powder was mainly attributed to the high crystallinity of the cubes. Copyright

Preparation of enantiomerically pure C76 with a general electrochemical method for the removal of Di(alkoxycarbonyl)methano bridges from methanofullerenes: The retro-bingel reaction

Serendipitously discovered during electrochemical investigations on the stability of anion 1, a preparatively useful electrochemical procedure, the retro-Bingel reaction, has been identified as a method for removing di(alkoxycarbonyl)methano bridges from methanofullerenes. This procedure was applied to prepare the first samples of enantiomerically pure D2-C76 with unambiguous optical purity.

Synthesis and properties of fullerene (C70) complexes of 2,6-bis(porphyrin)-substituted pyrazine derivatives bound to a Pd(II) ion

2,6-Bis(porphyrin)-substituted 3,5-dimethylpyrazine and its zinc complex bound C70 to yield 1:1 inclusion complexes, which were characterised by ESI-MS, UV-vis, fluorescence and NMR spectroscopies. Association constants of the C70 complexes were determined by fluorescence and NMR spectral analyses. A decrease in absorbance of the Soret band of the pyrazine derivative by the effect of C70 was observed, suggesting the existence of a charge transfer interaction between C70 and porphyrin. Experimentally reliable values for the association constants were obtained by the NMR method and were about six times larger than those of the corresponding C60 complexes. Palladium complexation of the porphyrin-pyrazine ligand was found to enhance the association with fullerene. The association constant of 2,6-bis(porphyrin-Zn)- substituted 3,5-dimethylpyrazine-Pd(II) complex with C70 was determined to be 8400±900M-1. From the comparison of the association constants, it was found that inclusion room for C70 in the Pd(II) complex was maintained, juxtaposed between porphyrins attached to the opposite sides of the pyrazine ligands.

Structural Phase Transformations in C70

Powder X-ray diffraction shows that on sublimation, solvent free C70 crystallizes in a hexagonal close packed (HCP1) arrangement with small admixture of a second hexagonal close placked (HCP2) phase as well as a face centred cubic (FCC) phase, the proportions of which are progressively transformed by annealing in vacuo at 300 deg C via HCP2 to FCC.