- Structure and properties of the Fullerene Dimer C140 produced by pressure treatment of C70
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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.
- Lebedkin, Sergei,Hull, William E.,Soldatov, Alexander,Renker, Burkhard,Kappes, Manfred M.
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- Electron Transfer from Tetrathiafulvalenes to Photoexcited C70 Studied by Observing Transient Absorption in the Near-IR Region
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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.
- Alam, Maksudul M.,Watanabe, Akira,Ito, Osamu
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- The chemical retro-Bingel reaction: Selective removal of bis(alkoxycarbonyl)methano addends from C60 and C70 with amalgamated magnesium
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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.
- Moonen, Nicolle N. P.,Thilgen, Carlo,Echegoyen, Luis,Diederich, Francois
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- Retro-cycloaddition reaction of pyrrolidinofullerenes
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(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.
- Martin, Nazario,Altable, Margarita,Filippone, Salvatore,Martin-Domenech, Angel,Echegoyen, Luis,Cardona, Claudia M.
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- Unimolecular dissociations of C70+ and its noble gas endohedral cations Ne@C70+ and Ar@C70 +: Cage-binding energies for C2 loss
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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.
- Cao, Baopeng,Peres, Tikva,Cross, R. James,Saunders, Martin,Lifshitz, Chava
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- Radical reaction of C70Cl10 with P(OEt)3: Isolation and characterization of C70[P(O)(OEt)2] nHn (n = 1, 2)
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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
- Khakina, Ekaterina A.,Yurkova, Anastasiya A.,Novikov, Artem V.,Piven, Nataliya P.,Chernyak, Alexander V.,Peregudov, Alexander S.,Troshin, Pavel A.
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- Self-crystallization of C70 cubes and remarkable enhancement of photoluminescence
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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
- Park, Chibeom,Yoon, Eunjin,Kawano, Masaki,Joo, Taiha,Choi, Hee Cheul
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- Preparation of enantiomerically pure C76 with a general electrochemical method for the removal of Di(alkoxycarbonyl)methano bridges from methanofullerenes: The retro-bingel reaction
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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.
- Kessinger, Roland,Crassous, Jeanne,Herrmann, Andreas,Ruettimann, Markus,Echegoyen, Luis,Diederich, Francois
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- Synthesis and properties of fullerene (C70) complexes of 2,6-bis(porphyrin)-substituted pyrazine derivatives bound to a Pd(II) ion
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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.
- Eda, Yusaku,Itoh, Kennosuke,Ito, Yoshio N.,Fujitsuka, Mamoru,Majima, Tetsuro,Kawato, Toshio
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- Structural Phase Transformations in C70
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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.
- Green, M. A.,Kurmoo, M.,Day, P.,Kikuchi, K.
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- Synthesis of [70]azafulleroids: Investigations of azide addition to C70
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Treatment of C70 with (2-methoxyethoxy)methyl azide gives rise to three out of a possible six triazoline isomers, showing chemoselectivity as well as regioselectivity. The major product arose from addition of azide to the double bond of C70 possessing the greatest local curvature. Selective thermolysis of the least stable triazoline, the one resulting from addition to the least curved [6,6] double bond, allowed solution of the structure of the three isomers. Thermolysis of the triazoline isomers produced mixtures of C70, azafulleroids, and fulleroaziridines.
- Bellavia-Lund, Cheryl,Wudl, Fred
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- Cage-Expansion of Fullerenes
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Despite the first proposal on the cage inflation of fullerenes in 1991, the chemical expansion of fullerenes has been still a formidable challenge. Herein, we provide an efficient methodology to expand [60] and [70]fullerene cages by the inclusion of totally C5N unit, giving nitrogen-containing closed structures as C65N and C75N with double fused heptagons. This method consists of two steps commenced with the construction of an opening by the reaction with triazine as a C3N source, followed by the cage reformation using N-phenylmaleimide as a C2 source. We also synthesized endohedral cages, demonstrating that the encapsulated H2O molecule inside the C75N cage prefers the orientation which maximizes the intramolecular interaction with the carbon wall. Additionally, we revealed the existence of a through-space magnetic dipolar interaction between the encapsulated H2 molecule and the embedded N atom.
- Zhang, Sheng,Hashikawa, Yoshifumi,Murata, Yasujiro
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supporting information
p. 12450 - 12454
(2021/08/20)
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- CF2-Bridged C60 Fullerene Dimers and their Optical Transitions
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Fullerene dyads bridged with perfluorinated linking groups have been synthesized through a modified arc-discharge procedure. The addition of Teflon inside an arc-discharge reactor leads to the formation of dyads, consisting of two C60 fullerenes bridged by CF2 groups. The incorporation of bridging groups containing electronegative atoms lead to different energy levels and to new features in the photoluminescence spectrum. A suppression of the singlet oxygen photosensitization indicated that the radiative decay from singlet-to-singlet state is favoured against the intersystem crossing singlet-to-triplet transition.
- Dallas, Panagiotis,Zhou, Shen,Cornes, Stuart,Niwa, Hiroyuki,Nakanishi, Yusuke,Kino, Yasuhiro,Puchtler, Tim,Taylor, Robert A.,Briggs, G. Andrew. D.,Shinohara, Hisanori,Porfyrakis, Kyriakos
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p. 3540 - 3543
(2017/11/22)
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- Lu2@C2n (2n = 82, 84, 86): Crystallographic Evidence of Direct Lu-Lu Bonding between Two Divalent Lutetium Ions Inside Fullerene Cages
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Although most of the M2C2n-type metallofullerenes (EMFs) tend to form carbide cluster EMFs, we report herein that Lu-containing EMFs Lu2C2n (2n = 82, 84, 86) are actually dimetallofullerenes (di-EMFs), namely, Lu2@Cs(6)-C82, Lu2@C3v(8)-C82, Lu2@D2d(23)-C84, and Lu2@C2v(9)-C86. Unambiguous X-ray results demonstrate the formation of a Lu-Lu single bond between two lutetium ions which transfers four electrons in total to the fullerene cages, thus resulting in a formal divalent state for each Lu ion. Population analysis indicates that each Lu atom formally donates a 5d electron and a 6s electron to the cage with the remaining 6s electron shared with the other Lu atom to form a Lu-Lu single bond so that only four electrons are transferred to the fullerene cages with the formal divalent valence for each lutetium ion. Accordingly, we confirmed both experimentally and theoretically that the dominating formation of di-EMFs is thermodynamically very favorable for Lu2C2n isomers.
- Shen, Wangqiang,Bao, Lipiao,Wu, Yongbo,Pan, Changwang,Zhao, Shasha,Fang, Hongyun,Xie, Yunpeng,Jin, Peng,Peng, Ping,Li, Fang-Fang,Lu, Xing
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supporting information
p. 9979 - 9984
(2017/08/02)
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- Unusual multistep reaction of C70Cl10 with thiols producing C70[SR]5H
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We report a reaction of the chlorofullerene C70Cl10 with thiols producing C70[SR]5H with all organic addends attached around one central pentagon at the pole of the C70 cage. This reaction was shown to proceed via a complicated radical pathway, presumably involving addition, substitution, rearrangement, and/or elimination steps. The obtained C70[SR]5H products were shown to be very unstable and undergo quantitative decomposition to pristine C70, RSSR, and RSH at elevated temperatures (e.g., 50 °C). Quantum chemical calculations and NMR spectroscopy data showed that cleavage of organic addends from the fullerene cage could be induced by solvation effects in solution.
- Khakina, Ekaterina A.,Peregudov, Alexander S.,Yurkova, Anastasiya A.,Piven, Natalya P.,Shestakov, Alexander F.,Troshin, Pavel A.
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p. 1215 - 1219
(2016/03/01)
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- Fullerene-Containing Hemicarceplexes and a Method of Purifying Fullerenes by Using the Same
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Fullerene⊙CTV complexes, comprising fullerene⊙CTV hemicarceplexes, formed by various cyclotriveratrylene (CTV)-based molecular cages and various fullerene guests are disclosed. A method of direct isolating at least a fullerene from fullerene mixtures by using the above fullerene CTV hemicarceplexes but without using crystallization or HPLC is also disclosed.
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Paragraph 0152-0159
(2014/05/07)
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- Reprint of: Preparation and UV/visible spectra of fullerenes C60 and C70
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The preparation and isolation of pure fullerene-60 and fullerene-70 is described. The solution UV/visible absorption spectra of the two molecules are presented.
- Hare,Kroto,Taylor
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- A Series of inorganic solid nitrogen sources for the synthesis of metal nitride clusterfullerenes: The dependence of production yield on the oxidation state of nitrogen and counter ion
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A series of nitrogen-containing inorganic solid compounds with variable oxidation states of nitrogen and counter ions have been successfully applied as new inorganic solid nitrogen sources toward the synthesis of Sc-based metal nitride clusterfullerenes (Sc-NCFs), including ammonium salts [(NH 4)xH3-xPO4 (x = 0-2), (NH 4)2SO4, (NH4)2CO 3, NH4X (X = F, Cl), NH4SCN], thiocyanate (KSCN), nitrates (Cu(NO3)2, NaNO3), and nitrite (NaNO2). Among them, ammonium phosphates ((NH4) xH3-xPO4, x = 1-3) and ammonium thiocyanate (NH4SCN) are revealed to behave as better nitrogen sources than others, and the highest yield of Sc-NCFs is achieved when NH4SCN was used as a nitrogen source. The optimum molar ratio of Sc2O 3:(NH4)3PO4·3H2O: C and Sc2O3:NH4SCN:C has been determined to be 1:2:15 and 1:3:15, respectively. The thermal decomposition products of these 12 inorganic compounds have been discussed in order to understand their different performances toward the synthesis of Sc-NCFs, and accordingly the dependence of the production yield of Sc-NCFs on the oxidation state of nitrogen and counter ion is interpreted. The yield of Sc3N@C80 (Ih + D5h) per gram Sc2O3 by using the N 2-based group of nitrogen sources (thiocyanate, nitrates, and nitrite) is overall much lower than those by using gaseous N2 and NH4SCN, indicating the strong dependence of the yield of Sc-NCFs on the oxidation state of nitrogen, which is attributed to the in-situ redox reaction taking place for the N2-based group of nitrogen sources during discharging. For NH3-based group of nitrogen sources (ammonium salts) which exhibits a (-3) oxidation states of nitrogen, their performance as nitrogen sources is found to be sensitively dependent on the anion, and this is understood by considering their difference on the thermal stability and/or decomposition rate. Contrarily, for the N2-based group of nitrogen sources, the formation of Sc-NCFs is independent to both the oxidation state of nitrogen (+3 or +5) and the cation.
- Liu, Fupin,Guan, Jian,Wei, Tao,Wang, Song,Jiao, Mingzhi,Yang, Shangfeng
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supporting information
p. 3814 - 3822
(2013/05/09)
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- Hemicarceplex formation with a cyclotriveratrylene-based molecular cage allows isolation of high-purity (≥99.0%) C70 directly from fullerene extracts
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A cyclotriveratrylene-based molecular cage that favors the formation of a room temperature isolable hemicarceplex with C70, in the presence of C60, has been developed. Significant differences in the association and dissociation kinetics of the molecular cage and buckyballs allowed the isolation of C70 in high purity (≥99.0%) from a commercial fullerene extract without the need for recrystallization or HPLC.
- Li, Ming-Jhe,Huang, Chi-Hao,Lai, Chien-Chen,Chiu, Sheng-Hsien
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supporting information
p. 6146 - 6149
(2013/03/14)
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- [(μ-H)3Re3 (CO) 9 (ν2, ν2,ν2-Sc2C2@C 3v(8)-C82)]: Face-capping cluster complex of an endohedral fullerene
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Fullerenes with atoms, ions, or clusters in their inner space are referred to as endohedral fullerenes. These spherical molecules have unique properties that can be very different from those of the empty fullerenes.[1, 2] Among these hybrid molecules, end
- Chen, Chia-Hsiang,Yeh, Wen-Yann,Liu, Yi-Hung,Lee, Gene-Hsiang
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supporting information
p. 13046 - 13049
(2013/03/13)
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- Construction and photophysics study of supramolecular complexes composed of three-point binding fullerene-trispyridylporphyrin dyads and zinc porphyrin
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A series of novel supramolecular complexes composed of a three-point binding C60-trispyridylporphyrin dyad (1) or C70- trispyridylporphyrin dyad (2) and zinc tetraphenylporphyrin (ZnP) were constructed by adopting a covalent-coordinate bonding approach, composed of three-point binding. The dyads and self-assembled supramolecular triads or pentads formed by coordinating the pyridine groups located on the dyads to ZnP, have been characterized by means of spectral and electrochemical techniques. The formation constants of ZnP-1 and ZnP-2 complexes were calculated as 1.4 × 104 M-1 and 2.0 × 104 M-1, respectively, and the Stern-Volmer quenching constants K SV were founded to be 2.9 × 104 M-1 and 5.5 × 104 M-1, respectively, which are much higher than those of other supramolecular complexes such as previously reported ZnP-3 (N-ethyl-2-(4-pyridyl)-3,4-fulleropyrrolidine). The electrochemical investigations of these complexes suggest weak interactions between the constituents in the ground state. The excited states of the complexes were further monitored by time-resolved fluorescence measurements. The results revealed that the presence of the multiple binding point dyads (1 or 2) slightly accelerated the fluorescence decay of ZnP in o-DCB relative to that of the single-point bound supramolecular complex ZnP-3. In comparison with 1 and 2, C70 is suggested as a better electron acceptor relative to C60. DFT calculations on a model of supramolecular complex ZnP-1 (with one ZnP entity) were performed. The results revealed that the lowest unoccupied molecular orbital (LUMO) is mainly located on the fullerene cage, while the highest occupied molecular orbital (HOMO) is mainly located on the ZnP macrocycle ring, predicting the formation of radical ion pair ZnP +-H2P-C60- during photo-induced reaction.
- Xu, Wei,Feng, Lai,Wu, Yishi,Wang, Taishan,Wu, Jingyi,Xiang, Junfeng,Li, Bao,Jiang, Li,Shu, Chunying,Wang, Chunru
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p. 428 - 433
(2014/03/21)
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- Direct arc-discharge assisted synthesis of C60H 2(C3H5N): A cis-1-pyrrolino C60 fullerene hydride with unusual redox properties
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By direct arc synthesis of C60H2(C3H 5N) using a modified Kraetschmer-Huffman method, it is demonstrated for the first time that exohedral fullerenes with large side groups can be formed under the arc and reactive gas atmosphere conditions. The thus formed novel pyrrolino fullerene hydride was comprehensively characterized by UV-vis, infrared (IR), Raman and nuclear magnetic resonance (NMR) and studied by means of electrochemistry and in situ electron spin resonance/visible-near infrared (ESR/Vis-NIR) spectroelectrochemistry. The detailed NMR and absorption spectroscopic studies show C60H2(C3H 5N) as the fullerene hydride with a pyrrolino ring attached on the vicinal position of two hydrogen atoms. This first cycloaddition adduct of C60H2 gives rise to an unusual reversible dimerization of its anion radicals and a loss of cage hydrogen atoms at the third electron transfer. The spectroelectrochemical study confirms the formation of a [C 60H2(C3H5N)]- radical and the diamagnetic state of [C60H2(C3H 5N)] 2-. This study reveals a unique function of a carbide structure like Al4C3 and the presence of a reactive gas atmosphere with NH3 in the formation of such an exohedral pyrrolino structure C60H2(C3H5N).
- Chen, Ning,Klod, Sabrina,Rapta, Peter,Popov, Alexey A.,Dunsch, Lothar
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experimental part
p. 2608 - 2615
(2011/11/12)
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- A new exTTF-crown ether platform to associate fullerenes: Cooperative n-π and π-π Effects
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A new and readily available exTTF-bis(crown ether), 1, efficiently recognizes C60 as well as C70 by means of cooperative π-π and n-π interactions. The geometrical (concave-convex) and electronic (donor-acceptor) complementarity accounts on one hand for remarkable binding strengths, with association constants reaching 107 M -1 in benzonitrile, and on the other hand for lifetimes of the photogenerated radical ion pair state on the order of 45 ps.
- Grimm, Bruno,Santos, Jose,Illescas, Beatriz M.,Munoz, Antonio,Guldi, Dirk M.,Martin, Nazario
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supporting information; body text
p. 17387 - 17389
(2011/02/23)
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- Simple combustion production and characterization of octahydro[60]fullerene with a non-IPR C60 cage
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For the first time an easier, operable combustion method is employed for the synthesis of non-IPR fullerene, and an octahydro[60]fullerene with a non-IPR C60 cage (C60 isomer #1809C60) produced by combustion is isolated and characterized by MS, UV-vis, IR, and NMR spectroscopies in combination with DFT calculations. This finding shows that, in addition to chlorine, hydrogen can be an ample cataloreactant for the production of non-IPR fullerene derivatives under such conditions as arc-burning and diffusion combustion.
- Weng, Qun-Hong,He, Qiao,Liu, Ting,Huang, Hui-Ying,Chen, Jian-Hua,Gao, Zhi-Yong,Xie, Su-Yuan,Lu, Xin,Huang, Rong-Bin,Zheng, Lan-Sun
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p. 15093 - 15095
(2010/12/20)
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- Synthesis of germanium encapsulated fullerene
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A method has been described for encapsulating Ge in a fullerene cage using GeO2 and a graphite composite rod as anode and graphite as cathode. Annealing in an inert atmosphere before arcing, and the amount of GeO2 in the rod determin
- Roy, Debmalya,Tripathi,Ram,Sathyamurthy
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p. 1244 - 1247
(2009/12/02)
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- Metallofullerols and their Applications for Preparation of Medicine for Inhibition of Tumor Growth
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This invention provides a composition of polyhydroxylated metallofullerene compound and its application in the preparation of antitumor pharmaceutical. In one embodiment, metallofullerol comprising the formula, M@C2m(OH)x, wherein M is selected from rare earth elements such as La or Gd; m is carbon atoms of 41 or 30; x is a number of hydroxyl group of from 10 to about 50. Actually, due to the reset of the neighboring hydroxyl, the numbers of O and H in Carbon cage are different, formula are thus written as M@C2mOxHy. Comparing to the clinical anticancer drugs such as Paclitaxel, Cyclophosphamide, and Cisplatin, metallofullerol of M@C2m(OH)x or M@C2mOxHy has superior advantages of higher antitumor efficiency, low dosage, low toxicity, and better biocompatibility.
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Page/Page column 3
(2009/04/24)
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- C60-C70-C6H5CH3 crystal solvates: Structure and thermal stability
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Differential scanning calorimetry (DSC) and X-ray diffraction were used to study the thermal stability and structure of C60-C 70-C6H5CH3 crystal solvates synthesized at room temperature. The decomposi
- Eremina,Lad'Yanov,Nikonova
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p. 2207 - 2212
(2009/04/12)
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- Endohedral gadolinium-containing metallofullerenes in the trifluoromethylation reaction
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An efficient method for the synthesis of trifluoromethyl derivatives of endohedral gadolinium-containing metallofullerenes was proposed. High-purity (98-99%) trifluoromethyl derivatives Gd@C82(CF3) 5 (two isomers) and Gds
- Kareev,Bubnov,Yagubskii
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p. 1486 - 1491
(2009/09/30)
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- The solubility of fullerene C70 in monocarboxylic acids C n - 1H2n - 1COOH (n = 1-9) over the temperature range 20-80°C
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The isothermal (20°C) solubility of fullerene C70 in solvents of the homologous series of monocarboxylic acids C n - 1H2n - 1COOH (n = 1-9) and polythermal solubility over the temperature range 20-80°C of fullerene C7
- Semenov,Charykov,Arapov,Keskinov,Pyartman,Gutenev,Proskurina,Matuzenko,Klepikov
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p. 1045 - 1047
(2008/12/21)
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- Technology for manufacture of pure fullerenes C60, C 70 and a concentrate of higher fullerenes
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An integrated technology for manufacture of fullerenes was developed. It includes the following stages: synthesis of a fullerene black, extraction of a mixture of fullerenes from the black, preliminary separation of the mixture into concentrates enriched in C60 and C70 fullerenes, and production of C60 and C70 fullerenes of purity exceeding 99.5 and 98.0 wt %, respectively, from the concentrates.
- Grushko,Sedov,Shilin
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p. 448 - 455
(2008/02/03)
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- Single-stage plasma-arc synthesis of metallo-endofullerences
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Single-stage plasma-arc synthesis of metallo-endofullerences of the types C60Pd, C60Ni, and C60Cr, whose content in a mixture of extracted fullerenes was 0.05 to 0.15 wt %, was performed. The effect of introduction of these metals into the reaction plasma on the total yield of fullerenes and on the fraction composition of the fullerene mixture was studied. The fullerene mixtures were analyzed by mass spectrometry and liquid chromatography.
- Gerasimov,Kalinin,Nikonov,Titovets,Kalabushkin,Alekhin,Nekrasov,Rusetskaya,Arapov,Alekseev,Kustova,Lishchuk,Pleshkov,Semenov,Keskinov,Charykov
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p. 1888 - 1893
(2008/04/05)
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- C48 buckybowl and C60 fullerene precursors on the basis of truxenone
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The synthesis of bromine-substituted truxenone derivatives which constitute prospective precursors of geodesic structures is presented. The underlying mechanism of fullerene formation from truxenone-based precursors during flash pyrolysis is discussed. Isolable quantities of C60 fullerene have been achieved by intramolecular condensation of a precursor containing all 60 carbon atoms in appropriate positions, 72 out of the 90 required C-C bonds, and 3 bromine atoms.
- Amsharov, Konstantin Yu.,Jansen, Martin
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p. 1497 - 1508
(2008/10/09)
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- Chemically Adjusting Plasma Temperature, Energy, and Reactivity (CAPTEAR) method using NOx and combustion for selective synthesis of Sc 3N@C80 metallic nitride fullerenes
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Goals are (1) to selectively synthesize metallic nitride fullerenes (MNFs) in lieu of empty-cage fullerenes (e.g., C60, C70) without compromising MNF yield and (2) to test our hypothesis that MNFs possess a different set of optimal formation parameters than empty-cage fullerenes. In this work, we introduce a novel approach for the selective synthesis of metallic nitride fullerenes. This new method is Chemically Adjusting Plasma Temperature, Energy, and Reactivity (CAPTEAR). The CAPTEAR approach with copper nitrate hydrate uses NOx vapor from NOx generating solid reagents, air, and combustion to tune the temperature, energy, and reactivity of the plasma environment. The extent of temperature, energy, and reactive environment is stoichiometrically varied until optimal conditions for selective MNF synthesis are achieved. Analysis of soot extracts indicate that percentages of C60 and Sc3N@C80 are inversely related, whereas the percentages of C70 and higher empty-cage C2n fullerenes are largely unaffected. Hence, there may be a competitive link in the formation and mechanism of C60 and Sc3N@C80. Using this CAPTEAR method, purified MNFs (96% Sc3N@C80, 12 mg) have been obtained in soot extracts without a significant penalty in milligram yield when compared to control soot extracts (4% Sc3N@C80, 13 mg of Sc3N@C 80). The CAPTEAR process with Cu(NO3)2· 2.5H2O uses an exothermic nitrate moiety to suppress empty-cage fullerene formation, whereas Cu functions as a catalyst additive to offset the reactive plasma environment and boost the Sc3N@C80 MNF production.
- Stevenson, Steven,Thompson, M. Corey,Coumbe, H. Louie,Mackey, Mary A.,Coumbe, Curtis E.,Phillips, J. Paige
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p. 16257 - 16262
(2008/09/17)
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- Synthesis of endohedral di-and monometallofullerenes Y2@C 84, Ce2@C78, and M@C82 (M = Y, Ce)
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Endohedral metallofullerenes Y2@C84, Ce 2@C78, and M@C82 (M = Y, Ce) were synthesized by the electric arc method and isolated from the soot using extraction with o-dichlorobenzene. Pure (98%) endohedr
- Kareev,Bubnov,Yagubskii
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p. 2140 - 2144
(2008/09/19)
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- Transmutation of fullerenes
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Fullerenes were pyrolyzed by subliming them into a stream of flowing argon gas and then passing them through an oven heated to ～1000°C. C 76, C78, and C84 all readily lost carbons to form smaller fullerenes. In the case of C78, some isomerization was seen. Pyrolysis of 3He@C76 showed that all or most of the 3He was lost during the decomposition. C60 passes through the apparatus with no decomposition and no loss of helium.
- Cross, R. James,Saunders, Martin
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p. 3044 - 3047
(2007/10/03)
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- Synthesis of metallofullerenes by electric-arc method with a surface-modified electrode
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A method for synthesis of metallofullerenes by electric-arc sputtering of graphite, in which lanthanum compounds are deposited on the surface of a graphite electrode, was suggested. The influence exerted by the amount of deposited lanthanum on the yield of lanthanum was studied.
- Kuz'min,Borovkov,Kolker,Brazhyunas
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p. 559 - 564
(2007/10/03)
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- Purification of endohedral trimetallic nitride fullerenes in a single, facile step
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A major hurdle hampering the development of fullerenes, endohedral metallofullerenes, and nanotubes has been the difficulty of obtaining high purity samples. Soots prepared in the usual manner via a Kraetschmer-Huffman electric-arc generator consist of mixtures of insoluble carbonaceous materials and soluble fullerenes: C60, C70, C76, C 78, C84, etc. When metals are introduced as endohedral species the complexity of the resultant soot is even greater because of the presence of multiple isomers of both the empty fullerenes and the endohedral metallofullerenes. Here, for the first time, we report that lanthanide trimetallic nitride endohedral metallofullerenes, A3N@C80 (A = lanthanide atom, e.g., Er, Gd, Ho, Lu, Sc, Tb, Tm, Y), can be obtained in pure form directly from as-prepared soots in a single facile step by taking advantage of their extraordinary kinetic chemical stability with respect to the other fullerenes in Diels-Alder reactions with a cyclopentadiene-functionalized resin. We show that careful control of conditions (stoichiometry, time, temperature) allows separation of fullerenes with different cage sizes, as well as isomeric species. Furthermore, the Diels-Alder reaction is thermally reversible, and we demonstrated that the bound empty-cage fullerenes and classical endohedral metallofullerenes can be recovered by displacement with maleic anhydride.
- Ge, Zhongxin,Duchamp, James C.,Cai, Ting,Gibson, Harry W.,Dorn, Harry C.
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p. 16292 - 16298
(2007/10/03)
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- Magnetic moments of the endohedral cluster fullerenes Ho 3N@C80 and Tb3N@C80: The role of ligand fields
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(Figure Presented) Wait a moment: The strong ligand field within the M 3N cluster of the endohedral cluster fullerenes Ho 3N@C80 and Tb3N@C80 accounts for the unusual net magnetic moment of the compounds. As a result of these interactions the individual magnetic moments m of the metal ions (M = Ho or Tb) are not parallel or antiparallel to each other, but parallel to the M-N bond (see scheme).
- Wolf, Manfred,Mueller, Karl-Hartmut,Skourski, Yurii,Eckert, Dieter,Georgi, Petra,Krause, Matthias,Dunsch, Lothar
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p. 3306 - 3309
(2007/10/03)
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- Methodology for the Preparation of C1-Monoalkylated 1,2-Dihydro[C 70] Derivatives: Formation of the Other Regioisomer
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Deprotonation of 1,2-C70H2 with TBAOH, followed by alkylation with methyl bromoacetate, results in formation of a C1-monoalkylated 1,2-dihydro-C70 derivative. The position of the alkyl group (C1) was established by NMR spectroscopy and comparison with literature spectra of C2-monoalkylated analogs. Presumably, C1-alkylation is the major process due to selective deprotonation of 1,2-C70H2 at C1. Substitution of benzyl bromide for methyl bromoacetate results in rapid dialkylation, unless the amount of base is carefully controlled, in which case C1-monobenzylation is the major process. This methodology for alkylation at C1 is complimentary to methods for the C2-monoalkylation of C70 with Zn and methyl bromoacetate.
- Wang, Zhongwen,Meier, Mark S.
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p. 2178 - 2180
(2007/10/03)
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- Significant promotional effect of CCl4 on fullerene yield in the graphite arc-discharge reaction
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Addition of a small quantity (～3%) of CCl4 to the He atmosphere of the graphite arc-discharge reaction revealed a marked increase in fullerene yield.
- Gao, Fei,Xie, Su-Yuan,Huang, Rong-Bin,Zheng, Lan-Sun
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p. 2676 - 2677
(2007/10/03)
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- Irradiation of CW-CO2 laser on a powder target. Formation of fullerene film from graphite powder
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A process was investigated to irradiate a continuous-wave CO2 laser (4.5 kW) on graphite powder with a mean diameter of 5 μm in a flow of Ar or He gas at 30 or 200 Torr. The film produced on a Ni substrate in the Ar flow at 200 Torr showed the Raman bands of C60 and C70, and the C60/C70 ratio was estimated to be 5/1 by MALDI-TOF mass spectrometry. The film formation process is discussed on the basis of an analysis of laser-irradiated powder, which included 0.01 wt% of C60, by UV-Vis absorption, and by observations of the plumes and SEM images.
- Kano, Seisuke,Kohno, Masamichi,Sakiyama, Kaname,Sasaki, Shinya,Aya, Nobuhiro,Shimura, Hirofumi
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p. 474 - 480
(2008/10/09)
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- First soluble M @ C60 derivatives provide enhanced access to metallofullerenes and permit in vivo evaluation of Gd @ C60[C(COOH)2]10 as a MRI contrast agent
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M @ C60 and related endohedral metallofullerenes comprise a significant portion of the metallofullerene yield in the traditional arc synthesis, but their chemistry and potential applications have been largely overlooked because of their sparse solubility. In this work, procedures are described to solublize Gd @ C60 species for the first time by forming the derivative, Gd @ C60[C(COOCH2CH3)2]10, and its hydrolyzed water-soluble form, Gd @ C60[C(COOH)2]10. Imparting water solubility to Gd @ C60 permits its evaluation as a magnetic resonance imaging (MRI) contrast agent. Relaxometry measurements for Gd @ C60[C(COOH)2]10 reveal it to possess a relaxivity (4.6 mM-1 s-1 at 20 MHz and 40 °C) comparable to that of commercially available Gd(III) chelate-based MRI agents. An in vivo MRI biodistribution study in a rodent model reveals Gd @ C60[C(COOH)2]10 to possess the first non-reticuloendothelial system (RES) localizing behavior for a water-soluble endohedral metallofullerene species, consistent with its lack of intermolecular aggregation in solution as determined by light-scattering measurements. This first derivatization and use of a M @ C60 species suggests new potential for metallofullerene technologies by reducing reliance on the chromatographic purification procedures normally employed for the far less abundant M @ C82 and related endohedrals. The recognition that water-soluble fullerene derivatives can be designed to avoid high levels of RES uptake is an important step toward fullerene-based pharmaceutical development.
- Bolskar, Robert D.,Benedetto, Angelo F.,Husebo, Lars O.,Price, Roger E.,Jackson, Edward F.,Wallace, Sidney,Wilson, Lon J.,Alford, J. Michael
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p. 5471 - 5478
(2007/10/03)
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- Residence time effect on fullerene yield in butadiene-based laser pyrolysis flame
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A new route for fullerene synthesis by CO2-laser pyrolysis of gas phase mixture is proposed. Small hydrocarbon molecules which absorb the laser radiation, such as butadiene, are mixed with nitrous oxide (N 2O) as oxidizer. Such a mixture allows avoiding the use of a photosensitizer as SF6 which causes contamination of the reaction zone and possibly influences the growth of fullerenic structures. This Letter also confirms the strong influence of the C/O atomic ratio in the mixture on the fullerene yield, and shows that residence time of the reactants in the pyrolysis flame and pressure influence dramatically the fullerene formation.
- Ténégal,Voicu,Armand,Herlin-Boime,Reynaud
-
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- Production, isolation and structural characterization of [92]fullerene isomers
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High-resolution 13C NMR has been used to structurally characterize a single isomer possessing C2 molecular sym)metry as well as an inseparable mixture of other isomers of [92]fullerene, produced from dysprosium arc-burned soot, separ
- Tagmatarchis, Nikos,Arcon, Denis,Prato, Maurizio,Shinohara, Hisanori
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p. 2992 - 2993
(2007/10/03)
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- Influence of nitrogen on carbon arc plasma and formation of fullerenes
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The influence of nitrogen on the process of fullerene formation in the carbon arc discharge in a helium/nitrogen atmosphere has been studied. Applying optical emission spectroscopy and using the self-absorption effect, the spatial distribution of the temp
- Lange,Huczko
-
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- Synthesis, separation, and characterization of fullerenes and their chlorinated fragments in the glow discharge reaction of chloroform
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Fullerenes and various chlorinated carbon clusters were synthesized via the glow discharge reaction using chloroform vapor as starting reactant. High-performance liquid chromatography combined with ultraviolet spectrometry and mass spectrometry (HPLC-UV-M
- Xie, Su-Yuan,Huang, Rong-Bin,Deng, Shun-Liu,Yu, La-Jia,Zheng, Lan-Sun
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p. 1734 - 1738
(2007/10/03)
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- New EPR signals of endohedral metallofullerenes
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The EPR spectra of endohedral metallofullerenes (EMF), La-EMF and Y-EMF, which were free of admixtures of C60 and of other empty fullerenes, were examined. Endohedral metallofullerenes were prepared by extraction of fullerene-containing soots with DMF. New signals with g factors close to those of fullerene radical anions were observed in the EPR spectra of solutions of EMF in DMF and DMSO. At ～20 °C, these signals are observed as a doublet (ΔHpp ≈ 0.04 mT) and singlet (ΔHpp ≈ 0.01 mT) in solutions of La-EMF and Y-EMF, respectively. These EPR signals belong to solvated La@C82 and Y@C82 molecules and are characterized by small hyperfine interaction constants aM due to a substantial decrease in the spin density of the unpaired electron at the metal atom.
- Koltover,Estrin,Bubnov,Laukhina
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p. 1745 - 1748
(2007/10/03)
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- Electronic structure of Eu@C60 studied by XANES and UV-VIS absorption spectra
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Eu endohedral C60, Eu@C60, has been extracted with aniline from soot prepared by arc-heating of a graphite/Eu2O3 composite rod and obtained at high concentration by combining sublimation and repeated high-performance liquid chromatography. The laser desorption time-of-flight mass spectrum showed a pronounced peak of Eu@C60+. The UV-VIS absorption spectrum of this sample has a red-shift in the onset (>900 nm) in comparison with those for C60 and C70, as expected from electron transfer from the Eu atom to the C60 cage. The valence state of the Eu atom in Eu@C60 has been determined to be +2 by Eu LIII-edge XANES.
- Inoue,Kubozono,Kashino,Takabayashi,Fujitaka,Hida,Inoue,Kanbara,Emura,Uruga
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p. 381 - 386
(2008/10/08)
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- Isolation and crystallographic characterization of ErSc2N@C80: An endohedral fullerene which crystallizes with remarkable internal order
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The ErnSc3-nN@C80 (n = 0-3) family of four endohedral fullerenes has been prepared by vaporization of graphite rods packed with 2% Sc2O3/3% Er2O3/95% graphite powder in a Kraetschmer-Huffman fullerene generator under dynamic flow of helium and dinitrogen. ErSc2N@C80 has been isolated in pure form via three stages of high-pressure liquid chromatography and characterized by mass spectrometry. The first structure of a mixed metal endohedral, ErSc2N@C80, has been determined by single-crystal X-ray diffraction at 90 K on ErSc2N@C80·CoII(OEP)·1.5C 6H6·0.3CHCl3, which was obtained by diffusion of a solution of ErSc2N@C80 in benzene into a solution of CoII(OEP) (OEP is the dianion of octaethylporphyrin) in chloroform. The structure of ErSc2N@C80 consists of a planar ErSc2N unit surrounded by an icosahedral C80 cage. The nominal Er-N distance is 2.089(9) A and the Sc-N distance is, as expected, shorter, 1.968(6) A. Despite its location within the C80 cage, the ErSc2N unit displays a remarkable degree of order within the solid-state structure. The metal ions make close contact with individual carbon atoms of the cage with shortest Sc-C distances, in the range of 2.03-2.12 A, and shortest Er-C distances of 2.20 and 2.22 A. Two different, but equally populated, orientations of the Ih C80 cage were required to describe the fullerene portion of the structure. Although these C80 cages are located on a crystallographic mirror plane, that plane does not coincide with a mirror plane of the cages themselves. Consequently, the cage is disordered over four superimposed sites.
- Olmstead,De Bettencourt-Dias,Duchamp,Stevenson,Dorn,Balch
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p. 12220 - 12226
(2007/10/03)
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- Photoinduced electron transfer between C70 fullerene and 3,3',5,5'-tetramethylbenzidine studied by electron paramagnetic resonance.
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Electron paramagnetic resonance (EPR) in situ spectroscopy was applied in the study of photoinduced electron transfer between 3,3',5,5'-tetramethylbenzidine (TMB) and C70 in different solvent systems. The changes found in UV-vis spectra pointed at ground state charge transfer complex formation [C70-TMB] in benzonitrile. Upon selective excitation of C70 using steady-state monochromatic irradiation with a wavelength of 546 nm, two EPR singlets were observed, which were assigned to C70 mono- and di-anion. In the photochemical and cathodic in situ reductions, identical EPR spectra of anion radicals were obtained. C70 mono-anion was investigated also in frozen 1,2-dichlorobenzene solutions within the temperature range from 110 to 210 K, and at 110 K the anisotropic EPR spectrum of C70 mono-anion was simulated assuming an axially symmetric g-matrix with gparallel - gperpendicular = 0.00165.
- Brezova,Dvoranova,Rapta,Stasko
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p. 2729 - 2739
(2007/10/03)
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- Hydrogen adsorption and phase transitions in fullerite
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Hydrogen desorption and adsorption properties of the fullerene materials C60, C70, and fullerite (a mixture of C60 and C70) were measured volumetrically using a Sievert's apparatus. Over several cycles of isotherm measurements at 77 K, the hydrogen storage capacities of one of the fullerite samples increased from an initial value of 0.4 wt% for the first cycle to a capacity of 4.4 wt% for the fourth cycle. Correspondingly, the surface area of this sample increased from 0.9 to 11 m2/g, and there were changes in its x-ray powder diffraction pattern. In comparison, two other fullerite samples, prepared by a different procedure showed no such behavior. Pure C60 and pure C70 were also cycled and exhibited small and constant capacities of 0.7 and 0.33 wt%, respectively, as a function of number of cycles. The enhanced storage capacity of fullerite material is tentatively attributed to the presence of C60 oxide.
- Ye,Ahn,Fultz,Vajo,Zinck
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p. 2171 - 2173
(2008/10/08)
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- Influence of Fe and Co/Ni on carbon arc plasma and formation of fullerenes and nanotubes
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Carbon nanostructures (fullerenes and nanotubes) were obtained using the carbon arc technique employing homogeneous carbon-iron and carbon-cobalt-nickel anodes. The influence of these catalysts on the arc plasma was studied by optical emission spectroscop
- Huczko, Andrzej,Lange, Hubert,Sogabe, Toshiaki
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p. 10708 - 10712
(2007/10/03)
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- Production of fullerenes and single-wall carbon nanotubes by high-temperature pulsed arc discharge
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Fullerenes and single-wall carbon nanotubes (SWNTs) have been produced for the first time by the high-temperature pulsed arc-discharge technique, which has developed in this laboratory. Fullerenes are identified quantitatively by high-performance liquid chromatography (HPLC), and scanning electron microscopy (SEM) and transmission electron microscopy (TEM) observations reveal a significant amount of production of bundles of SWNTs in soot. The pulse arc production of fullerenes and SWNTs favors the high-temperature (≥ 1000°C), long pulses (≥ 1 ms) and a heavy rare gas such as Ar or Kr as a buffer gas. We have found that fullerenes and SWNTs have complementary relationships in their early stage of production. The details of the pulsed arc discharge have been obtained by observing the transition from the pulsed arc discharge to the steady arc discharge while increasing the pulse width.
- Sugai, Toshiki,Omote, Hideki,Bandow, Shunji,Tanaka, Nobuo,Shinohara, Hisanori
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p. 6000 - 6005
(2007/10/03)
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- Selective electrolytic removal of bis(alkoxycarbonyl)methano addends from C60 bis-adducts and electrochemical stability of C70 derivatives
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The novel mixed his-adducts of C60, (±)-4-(±)-8 and 9, with a bis(ethoxycarbonyl)methano addend (Bingel addend) and a second addend ([1,2]benzeno, but[2]eno, methaniminomethano, or diarylmethano) bridging 6,6-closed bonds of the carbon sphere were synthesized in two-step reactions. Each bis-adduct was exhaustively electrolyzed at the potential of the second fullerene-centered reduction step, resulting in the selective removal of the Bingel addend (retro-Bingel reaction) to produce the corresponding mono-adducts, which were isolated in yields of over 60%. These results open up the possibility of using the Bingel addend as a temporary protecting and directing group in the construction of multiple adducts of C60 with unusual addition patterns. The Bingel-type mono-adduct of C70 10 and the constitutionally isomeric bis-adducts 11, (±)-12, and (±)-13 were also included in this investigation. A large difference in the electrochemical behavior between C70, bis-adducts and the corresponding C60 derivatives was observed. Thus, the intramolecular "walk-on-the-sphere" isomerization which occurs readily with Bingel-type bis-adducts of C60 under the conditions of two-electron controlled potential electrolysis (CPE) is only a minor reaction pathway in the series of C70 derivatives. The latter preferentially undergo retro-Bingel reaction.
- Kessinger, Roland,Fender, Nicolette S.,Echegoyen, Lourdes E.,Thilgen, Carlo,Echegoyen, Luis,Diederich, Francois
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p. 2184 - 2192
(2007/10/03)
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- In situ laser-furnace TOF mass spectrometry of C36 and the large-scale production by arc-discharge
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A greatly improved synthesis of C36, obtained as its hydrides C36H4 and C36H6 and oxyhydrides C36H4O and C36H6O, via a high- temperature laser vaporization (laser-furnace) method and the conventional DC arcdischarge method is reported. We have found that doping metal catalysts such as Ni/Co or Ni/Y into the laser target graphite rod or the DC arc-discharge electrode, respectively, significantly enhanced the production of C36 species; the methods have been known for efficient production methods of single-wall carbon nanotubes (SWNTs). The results suggest that the catalytic formation of C36 species and SWNTs is closely related with each other in their early stage of formation. Furthermore, a molecular C36H6 gives C18H3 (in/z = 219) as a magic fragment upon desorption/ionization. By using a high-performance liquid chromatography (HPLC),. C36H6 was purified (99%) in milligram quantity for the first time. The purified C36H6 exists as a clusterassembled material such as oligomers or clusters in the solid state, not as a molecular crystal such as C60.
- Koshio, Akira,Inakuma, Masayasu,Wang, Zhong W.,Sugai, Toshiki,Shinohara, Hisanori
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p. 7908 - 7913
(2007/10/03)
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