1266:
304:
248:
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1420:) on the nanotube surface which electrostatically stabilize them in water and which can later be utilized in chemical functionalization. One report reveals that the oxygen containing groups in actuality combine with carbon contaminations absorbed to the nanotube wall that can be removed by a simple base wash. Cleaned nanotubes are reported to have reduced D/G ratio indicative of less functionalization, and the absence of oxygen is also apparent from
4578:
260:
4590:
4566:
33:
325:. Research in this field is driven by the need to functionalize fullerenes and tune their properties. For example, fullerene is notoriously insoluble and adding a suitable group can enhance solubility. By adding a polymerizable group, a fullerene polymer can be obtained. Functionalized fullerenes are divided into two classes:
1300:
was low: 0.1 to 1%. A small percentage of fullerenes is formed in any process which involves burning of hydrocarbons, e.g. in candle burning. The yield through a combustion method is often above 1%. The method proposed above does not provide any advantage for synthesis of fullerenes compared to the
709:
is only hypothetical because of large strain. Highly hydrogenated fullerenes are not stable, as prolonged hydrogenation of fullerenes by direct reaction with hydrogen gas at high temperature conditions results in cage fragmentation. At the final reaction stage this causes collapse of cage structure
455:
The double bonds in fullerene are not all the same. Two groups can be identified: 30 so-called double bonds connect two hexagons and 60 bonds connect a hexagon and a pentagon. Of the two the bonds are shorter with more double-bond character and therefore a hexagon is often represented as a
991:
form complexes with a variety of molecules. In the solid state lattice structures are stabilized by the intermolecular interactions. Charge transfer complexes are formed with weak electron donors. The double bond is electron-deficient and usually forms metallic bonds with η = 2
561:
when double bonds become saturated. Key in this type of reaction is the level of functionalization i.e. monoaddition or multiple additions and in case of multiple additions their topological relationships (new substituents huddled together or evenly spaced). In conformity with
1984:
Talyzin, A. V.; Tsybin, Y. O.; Purcell, J. M.; Schaub, T. M.; Shulga, Y. M.; Noréus, D.; Sato, T.; Dzwilewski, A.; Sundqvist, B.; Marshall, A. G. (2006). "Reaction of
Hydrogen Gas with C60at Elevated Pressure and Temperature: Hydrogenation and Cage Fragmentationâ ".
3047:
Keshavarz-K, M.; GonzĂĄlez, R.; Hicks, R. G.; Srdanov, G.; Srdanov, V. I.; Collins, T. G.; Hummelen, J. C.; Bellavia-Lund, C.; Pavlovich, J.; Wudl, F.; Holczer, K. (1996). "Synthesis of hydroazafullerene C59HN, the parent hydroheterofullerene".
1091:
whereby one or more bonds are removed chemically exposing an orifice. In this way it is possible to insert into it small molecules such as hydrogen, helium or lithium. The first such open-cage fullerene was reported in 1995. In
2876:
Pellarin, M.; Ray, C.; Lermé, J.; Vialle, J. L.; Broyer, M.; Blase, X.; Kéghélian, P.; Mélinon, P.; Perez, A. (1999). "Photolysis experiments on SiC mixed clusters: From silicon carbide clusters to silicon-doped fullerenes".
2481:
Roubelakis, M. M.; Vougioukalakis, G. C.; Orfanopoulos, M. (2007). "Open-Cage
Fullerene Derivatives Having 11-, 12-, and 13-Membered-Ring Orifices: Chemical Transformations of the Organic Addends on the Rim of the Orifice".
1769:
Weng, Q. H.; He, Q.; Liu, T.; Huang, H. Y.; Chen, J. H.; Gao, Z. Y.; Xie, S. Y.; Lu, X.; Huang, R. B.; Zheng, L. S. (2010). "Simple
Combustion Production and Characterization of Octahydrofullerene with a Non-IPR
3114:
Zhang, G.; Huang, S.; Xiao, Z.; Chen, Q.; Gan, L.; Wang, Z. (2008). "Preparation of
Azafullerene Derivatives from Fullerene-Mixed Peroxides and Single Crystal X-ray Structures of Azafulleroid and Azafullerene".
1809:
Prato, M.; Lucchini, V.; Maggini, M.; Stimpfl, E.; Scorrano, G.; Eiermann, M.; Suzuki, T.; Wudl, F. (1993). "Energetic preference in 5,6 and 6,6 ring junction adducts of C60: Fulleroids and methanofullerenes".
941:
from a suitable precursor the tBuC60 radical is formed that can be studied. The unpaired electron does not delocalize over the entire sphere but takes up positions in the vicinity of the tBu substituent.
1961:
Darwish, A. D.; Avent, A. G.; Taylor, R.; Walton, D. R. M. (1996). "Reaction of benzyne with fullerene gives four monoadducts: Formation of a triptycene homologue by 1,4-cycloaddition of a fullerene".
2917:
Billas, I.M.L.; Branz, W.; Malinowski, N.; Tast, F.; Heinebrodt, M.; Martin, T.P.; Massobrio, C.; Boero, M.; Parrinello, M. (1999). "Experimental and computational studies of heterofullerenes".
448:
to a sp orbital with a gain in p-character. The p lobes extend further outside the surface than they do into the interior of the sphere and this is one of the reasons a fullerene is
3205:
Komatsu, K.; Wang, G. W.; Murata, Y.; Tanaka, T.; Fujiwara, K.; Yamamoto, K.; Saunders, M. (1998). "Mechanochemical
Synthesis and Characterization of the Fullerene Dimer C120".
1319:
A similar exercise aimed at construction of a C78 cage in 2008 (but leaving out the precursor's halogens) did not result in a sufficient yield but at least the introduction of
618:
stops quantitatively at the penta-adduct with the methyl groups centered around a cyclopentadienyl anion which is subsequently protonated. Another nucleophilic reaction is the
2089:
Chiang, L. Y.; Upasani, R. B.; Swirczewski, J. W.; Soled, S. (1993). "Evidence of hemiketals incorporated in the structure of fullerols derived from aqueous acid chemistry".
397:
has 24 IPR isomers of which several are isolated and another 51,568 non-IPR isomers. Non-IPR fullerenes have thus far only been isolated as endohedral fullerenes such as Tb
2217:
Kokubo, K.; Matsubayashi, K.; Tategaki, H.; Takada, H.; Oshima, T. (2008). "Facile
Synthesis of Highly Water-Soluble Fullerenes More Than Half-Covered by Hydroxyl Groups".
3551:"Kilogram-scale [60]Fullerene Separation from a Fullerene Mixture: Selective Complexation of Fullerenes with 1,8-Diazabicyclo[5.4.0]undec-7-ene (DBU)"
3440:
Kabdulov, M.; Jansen, M.; Amsharov, K. Yu (2013). "Bottom-Up C60 Fullerene
Construction from a Fluorinated C60H21F9 Precursor by Laser-Induced Tandem Cyclization".
3259:
Kunitake M, Uemura S, Ito O, Fujiwara K, Murata Y, Komatsu K (2002). "Structural
Analysis of C60 Trimers by Direct Observation with Scanning Tunneling Microscopy".
2411:
Cortés-Figueroa, J. E. (2003). "An
Experiment for the Inorganic Chemistry Laboratory: The Sunlight-Induced Photosynthesis of (η2-C60)M(CO)5 Complexes (M = Mo, W)".
385:
is the first stable fullerene because it is the smallest possible to obey this rule. In this structure none of the pentagons make contact with each other. Both C
2621:
Chai, Y.; Guo, T.; Jin, C.; Haufler, R. E.; Chibante, L. P. F.; Fure, J.; Wang, L.; Alford, J. M.; Smalley, R. E. (1991). "Fullerenes with metals inside".
2066:
Chiang, L. Y.; Swirczewski, J. W.; Hsu, C. S.; Chowdhury, S. K.; Cameron, S.; Creegan, K. (1992). "Multi-hydroxy additions onto C60 fullerene molecules".
3294:
Scott, L. T.; Boorum, M. M.; McMahon, B. J.; Hagen, S.; Mack, J.; Blank, J.; Wegner, H.; De
Meijere, A. (2002). "A Rational Chemical Synthesis of C60".
2446:
Vougioukalakis, G. C.; Roubelakis, M. M.; Orfanopoulos, M. (2010). "Open-cage fullerenes: Towards the construction of nanosized molecular containers".
1256:
fullerene is well established (generation of a large current between two nearby graphite electrodes in an inert atmosphere) a 2002 study described an
567:
2174:
Zhang, G.; Liu, Y.; Liang, D.; Gan, L.; Li, Y. (2010). "Facile Synthesis of Isomerically Pure Fullerenols and Formation of Spherical Aggregates from C
579:
2139:
Wang, S.; He, P.; Zhang, J. M.; Jiang, H.; Zhu, S. Z. (2005). "Novel and Efficient Synthesis of WaterâSoluble Fullerenol by SolventâFree Reaction".
3649:
2116:
Li, J.; Takeuchi, A.; Ozawa, M.; Li, X.; Saigo, K.; Kitazawa, K. (1993). "C60 fullerol formation catalysed by quaternary ammonium hydroxides".
3518:
Verdejo, R.; Lamoriniere, S.; Cottam, B.; Bismarck, A.; Shaffer, M. (2007). "Removal of oxidation debris from multi-walled carbon nanotubes".
2944:
Branz, W.; Billas, I. M. L.; Malinowski, N.; Tast, F.; Heinebrodt, M.; Martin, T. P. (1998). "Cage substitution in metalâfullerene clusters".
1354:
science and determines fullerene prices and the success of practical applications of fullerenes. The first available purification method for C
3750:
1385:
with a paper filter. The solvent is evaporated and the residue (the toluene-soluble soot fraction) redissolved in toluene and subjected to
795:
1304:
Continuous high-resolution transmission electron microscopic video imaging of the electron-beam-induced bottom-up synthesis of fullerene C
3755:
2862:
1400:
In nanotube processing the established purification method for removing amorphous carbon and metals is by competitive oxidation (often a
1934:
Hoke, S. H.; Molstad, J.; Dilettato, D.; Jay, M. J.; Carlson, D.; Kahr, B.; Cooks, R. G. (1992). "Reaction of fullerenes and benzyne".
801:
69:
3582:"Thio[2-(benzoylamino)ethylamino]-ÎČ-CD fragment modified gold nanoparticles as recycling extractors for [60]fullerene"
805:. Water solubility depends on the total number of hydroxyl groups that can be attached. One method is fullerene reaction in diluted
59:
2814:
Ohtsuki, T.; Ohno, K.; Shiga, K.; Kawazoe, Y.; Maruyama, Y.; Masumoto, K. (1999). "Formation of As- and Ge-doped heterofullerenes".
2349:
Tzirakis, Manolis D. (2013). "Radical Reactions of Fullerenes: From Synthetic Organic Chemistry to Materials Science and Biology".
889:
Protocols have been investigated for removing substituents via eliminations after they have served their purpose. Examples are the
3581:
3356:"A Singular Molecule-to-Molecule Transformation on Video: The Bottom-Up Synthesis of Fullerene C60 from Truxene Derivative C60H30"
3733:
290:
3272:
3777:
1359:
64:
2252:
Jia, J.; Wu, H. S.; Xu, X. H.; Zhang, X. M.; Jiao, H. (2008). "Fused Five-Membered Rings Determine the Stability of C60F60".
1265:
881:
may have some of the fluorine atoms in endo positions (pointing inwards) and may resemble a tube more than it does a sphere.
3789:
3728:
3232:
Komatsu, K.; Fujiwara, K.; Murata, Y. (2000). "The Mechanochemical Synthesis and Properties of the Fullerene Trimer C180".
1638:
3642:
107:
670:
Fullerenes are easily hydrogenated by several methods. The smallest perhydrogenated fullerene known is dodecahedrane C
2050:
1588:
1495:(CD). A separation method for both fullerenes based on this principle is made possible by anchoring cyclodextrin to
968:
is dictated by its spherical geometry and localized polyalkene Ï-electronic structure. All reported derivatives are
2594:
Hummelen, Jan C.; Bellavia-Lund, Cheryl; Wudl, Fred (1999). "Heterofullerenes. Fullerenes and Related Structures".
1425:
405:
with two fused pentagons at the apex of an egg-shaped cage. or as fullerenes with exohedral stabilization such as C
4594:
1273:
4473:
3635:
3354:
Lungerich, Dominik; Hoelzel, Helen; Harano, Koji; Jun, Norbert; Amsharov, Konstantin; Nakamura, Eiichi (2021).
1301:
usual combustion method, and therefore, the organic synthesis of fullerenes remains a challenge for chemistry.
181:
3916:
3670:
3091:
Nuber, B.; Hirsch, A. (1996). "A new route to nitrogen heterofullerenes and the first synthesis of (C69N)2".
1226:
1093:
201:
49:
4616:
1671:
Beavers, C. M.; Zuo, T.; Duchamp, J. C.; Harich, K.; Dorn, H. C.; Olmstead, M. M.; Balch, A. L. (2006). "Tb
141:
74:
841:
was prepared using a multistep procedure starting from a mixed peroxide fullerene. The maximum number of
4193:
3680:
303:
283:
3150:
Xin, N.; Huang, H.; Zhang, J.; Dai, Z.; Gan, L. (2012). "Fullerene Doping: Preparation of Azafullerene C
1472:
fullerenes do not have any affinity for DBU and are subsequently isolated. Other diamine compounds like
464:. In other words, although the carbon atoms in fullerene are all conjugated the superstructure is not a
4570:
4119:
4090:
4070:
4023:
972:
complexe in which the metal coordinates at a sixâsix ring fusion with formal double bond. No analogous
490:
3016:
3708:
2849:
Möschel, C.; Jansen, M. (1999). "Darstellung stabiler Phosphor-Heterofullerene im Hochfrequenzofen".
1242:
655:
631:
341:
156:
54:
4463:
4379:
4018:
2693:"Aza-dihydro[60]fullerene in the gas phase. A mass-spectrometric and quantumchemical study"
1552:
961:
615:
234:
186:
2322:
Tsuda, Minoru (1993). "C61Cl2. Synthesis and characterization of dichlorocarbene adducts of C60".
1323:
could be ruled out. C60 synthesis through a fluorinated fullerene precursor was reported in 2013
781:
atoms are equivalent. The only characterized iodine-containing compounds are intermediates: and
4401:
4312:
4275:
4159:
4085:
3906:
3889:
3832:
1503:-sulfur bridge. The Au/CD compound is very stable and soluble in water and selectively extracts C
914:
634:
type reaction. In this hydroarylation the reaction product is the 1,2-addition adduct (Ar-CC-H).
176:
829:
adding 24 to 26 hydroxyl groups. Hydroxylation has also been reported using solvent-free NaOH /
4319:
4307:
4198:
4063:
3837:
3703:
2980:
1461:
1277:
854:
493:
requires 72 electrons. The fullerene is able to acquire the missing electrons by reaction with
276:
1871:"Synthesis of 6,9,12,15,18-pentamethyl-1,6,9,12,15,18-hexahydro(c60-ih)[5,6]fullerene"
1468:
fullerenes and higher which reaction products separate out and can be removed by filtration. C
4468:
4365:
4350:
4280:
4203:
4035:
3985:
3894:
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1386:
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890:
607:
595:
437:
363:
353:
330:
191:
2518:
2384:
Morton, J. R. (1992). "ESR studies of the reaction of alkyl radicals with fullerene (C60)".
1679:: An Improbable, Egg-Shaped Endohedral Fullerene that Violates the Isolated Pentagon Rule".
4458:
4413:
4188:
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2995:
2953:
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2665:
2420:
1994:
1178:. Reports on isolated heterofullerenes are limited to those based on nitrogen and oxygen.
894:
647:
539:
In this compound the bond length alternation observed in the parent molecule has vanished.
374:
326:
229:
151:
112:
92:
861:
can add up to 24 bromine atoms to the sphere. The record holder for fluorine addition is C
336:
This article covers the chemistry of these so-called "buckyballs," while the chemistry of
8:
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997:
196:
161:
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3307:
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2999:
2957:
2890:
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1998:
452:. The other reason is that the empty low-lying Ï orbitals also have a high s character.
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4524:
4386:
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1374:
1320:
627:
558:
131:
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2648:
Muhr, H. -J.; Nesper, R.; Schnyder, B.; Kötz, R. (1996). "The boron heterofullerenes C
2335:
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4425:
4343:
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4266:
4251:
4221:
4142:
4109:
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3187:
3132:
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2800:
2709:
2692:
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2576:
2499:
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2304:
2269:
2234:
2199:
2046:
2010:
1916:
1875:
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1584:
1257:
1218:
951:
926:
830:
810:
472:
468:
441:
433:
318:
264:
171:
3033:
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1755:
917:
pyrolysis) was first reported in 1993. A single addition takes place along a bond.
557:
Fullerenes tend to react as electrophiles. An additional driving force is relief of
4582:
4499:
4154:
4013:
3990:
3943:
3884:
3592:
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2858:
2831:
2796:
2749:
2724:
Lamparth, I.; Nuber, B.; Schick, G.; Skiebe, A.; Grösser, T.; Hirsch, A. (1995). "C
2704:
2673:
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2568:
2533:
2491:
2455:
2428:
2393:
2358:
2331:
2296:
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2191:
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2121:
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2002:
1966:
1943:
1908:
1850:
1819:
1783:
1735:
1715:
1688:
1653:
1617:
1436:
A recent kilogram-scale fullerene purification strategy was demonstrated by Nagata
1293:
1214:
1096:
the opening, hydrogen insertion and closing back up has already been demonstrated.
822:
603:
465:
425:
337:
3344:
The numbers in image correspond to the way the new carbon carbon bonds are formed.
3007:
421:. Fullerenes with fewer than 60 carbons do not obey isolated pentagon rule (IPR).
4440:
4396:
4391:
4285:
4261:
4095:
4058:
3911:
3901:
3784:
3331:
1457:
1421:
1222:
1105:
910:
619:
548:
457:
449:
40:
1870:
377:
these 12 pentagons are required for closure of the carbon network consisting of
4324:
4302:
4297:
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4247:
4243:
4226:
4183:
4114:
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3970:
3955:
3767:
3685:
1496:
1347:
1297:
1285:
659:
552:
252:
166:
1408:
mixture). It is assumed that this oxidation creates oxygen containing groups (
4610:
4529:
4418:
4374:
4099:
3933:
3928:
3921:
3799:
2835:
1527:
which has a higher affinity for the cyclodextrin cavity. Au/CD is completely
1401:
1206:
1124:
996:. Bonding modes such as η = 5 or η = 6 can be induced by modification of the
806:
643:
623:
429:
219:
210:
146:
97:
24:
3371:
3315:
2863:
10.1002/(SICI)1521-3749(199902)625:2<175::AID-ZAAC175>3.0.CO;2-2
2607:
1855:
1838:
1739:
1622:
1605:
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4147:
4137:
4129:
4030:
3965:
3864:
3713:
3604:
3535:
3461:
3453:
3426:
3379:
3323:
3280:
3191:
3183:
3136:
3025:
2979:
Hummelen, J. C.; Knight, B.; Pavlovich, J.; Gonzalez, R.; Wudl, F. (1995).
2753:
2580:
2503:
2467:
2370:
2308:
2273:
2238:
2203:
2195:
2014:
1920:
1912:
1795:
1747:
1700:
1492:
1289:
1134:
1115:
591:
571:
428:, which has far-reaching consequences for reactivity. It is estimated that
122:
2152:
1365:
A practical laboratory-scale method for purification of soot enriched in C
3804:
3245:
3100:
2656:
B: Generation, extraction, mass spectrometric and XPS characterization".
2125:
2075:
1970:
1405:
934:
475:
136:
3627:
3566:
3405:
Fullerene Precursor: Toward the Direct Synthesis of Higher Fullerenes".
2634:
2537:
2397:
2102:
1947:
1823:
1292:
incubators and the ball was stitched up in a no-doubt complex series of
845:
groups that can be attached (hydrogen peroxide method) stands at 36â40.
729:
Fullerenes can react with halogens. The preferred pattern for addition C
4430:
3504:
3273:
10.1002/1521-3773(20020315)41:6<969::AID-ANIE969>3.0.CO;2-I
1524:
1516:
1382:
1151:
938:
650:. 4-membered rings can be obtained by cycloadditions for instance with
445:
3418:
3218:
3128:
2572:
2495:
2432:
2362:
2300:
2265:
2230:
2006:
1787:
1692:
1021:
molecules trapped in a hydrogen-bonded of 1,4-dihydroquinone molecules
733:
is calculated to be 1,9- for small groups and 1,7- for bulky groups. C
678:, formally derived from the smallest possible but unknown fullerene, C
424:
Because of the molecule's spherical shape the carbon atoms are highly
393:
obey this so-called isolated pentagon rule (IPR). The next homologue C
247:
4492:
3794:
3659:
3596:
3527:
3069:
2965:
2898:
2459:
1657:
1536:
1528:
1351:
1338:
compound free of contamination. In fullerene production mixtures of C
1335:
1230:
1147:
993:
870:
599:
575:
494:
479:
461:
436:. The conjugated carbon atoms respond to deviation from planarity by
322:
83:
2620:
2480:
2445:
1639:"[60]Fullerene chemistry for materials science applications"
4514:
2775:
O production and decomposition, charge transfer, and formation of C
1417:
1413:
1409:
1129:
842:
224:
1114:
at least one carbon atom is replaced by another element. Based on
602:
is captured by another electrophile. Examples of nucleophiles are
259:
4534:
1532:
1453:
1378:
1175:
1171:
1155:
1143:
930:
906:
858:
778:
651:
3517:
2690:
2216:
3046:
2978:
2691:
Averdung, J.; Luftmann, H.; Schlachter, I.; Mattay, J. (1995).
1581:
Fullerenes and Related Structures (Topics in Current Chemistry)
1508:
1500:
1276:
consisting of 13 hexagons and three pentagons was submitted to
1167:
1163:
1139:
1070:
957:
1362:
from which small amounts could be generated at large expense.
3548:
2088:
2065:
1473:
1119:
563:
3549:
Nagata, K.; Dejima, E.; Kikuchi, Y.; Hashiguchi, M. (2005).
2981:"Isolation of the Heterofullerene C59N as Its Dimer (C59N)2"
1189:
O are observed in minor in fullerene-containing soot. Only C
4509:
1899:-Mediated Mono-, Di-, and Trihydroarylation of Fullerene".
1808:
1578:
1281:
1159:
826:
749:
gas at 250 °C to a material with average composition C
642:
The bonds of fullerenes react as dienes or dienophiles in
32:
2287:
Yamada, Michio (2013). "Carbene Additions to Fullerenes".
1983:
717:
reacts with Li to the weak base , which is isolated as Li
4519:
3353:
3258:
2943:
2916:
2723:
2593:
1193:
O is isolated as a pure compound in macroscopic amounts.
2118:
Journal of the Chemical Society, Chemical Communications
2068:
Journal of the Chemical Society, Chemical Communications
1960:
1260:
of the compound starting from simple organic compounds.
3293:
3204:
2813:
2767:
Christian, J. F.; Wan, Z.; Anderson, S. L. (1992). "O+C
2559:
Vostrowsky, O.; Hirsch, A. (2006). "Heterofullerenes".
1933:
1839:"Recent advances in the chemistry of bridged annulenes"
1670:
1431:
1221:
as a catalyst. The trimer has also been reported using
3439:
2875:
2647:
1963:
Journal of the Chemical Society, Perkin Transactions 2
1894:
3474:
3231:
2848:
1087:
A part of fullerene research is devoted to so-called
909:
to methanofullerenes. The reaction of fullerene with
2766:
1895:
Iwashita, A.; Matsuo, Y.; Nakamura, E. (2007). "AlCl
1350:
are always formed. Fullerene purification is key to
761:
can be detected by mass spectrometry. With liquid Br
710:
with formation of polycyclic aromatic hydrocarbons.
347:
1452:and higher fullerene compounds by first adding the
3113:
2742:Angewandte Chemie International Edition in English
2516:
2115:
1252:Although the procedure for the synthesis of the C
4608:
3149:
2558:
2173:
2138:
1716:"Capturing the Labile Fullerene[50] as C
1523:is driven out from the Au/CD compound by adding
1247:
929:. With a simple hydrocarbon radical such as the
373:with 12 pentagons and 20 hexagons. According to
2410:
1531:when adamantol in turn is driven out by adding
3475:Spencer, T.; Yoo, B.; Kirshenbaum, K. (2006).
3400:
1768:
1515:fullerene component is then removed by simple
3643:
3477:"Purification and Modification of Fullerene C
2517:Hummelen, J. C.; Prato, M.; Wudl, F. (1995).
1011:molecules are arranged in close-packed layers
284:
2251:
1714:Xie, SY; Gao, F; Lu, X; et al. (2004).
1579:Hirsch, A.; Bellavia-Lund, C., eds. (1993).
682:, which comprises just 12 pentagonal faces.
3579:
3090:
3650:
3636:
3017:11370/ffe5ba8c-5336-4aed-9c78-0a26f31d459d
1397:is next displaying a reddish-brown color.
1225:as catalyst (4% yield) and observed with
848:
482:for the bond and 145.5 pm for the bond.
291:
277:
3657:
3015:
2912:
2910:
2908:
2708:
1854:
1621:
1603:
585:
578:derivatives, and fulleroid to ring-open (
3401:Amsharov, K. Y.; Jansen, M. (2008). "A C
3117:Journal of the American Chemical Society
2526:Journal of the American Chemical Society
2348:
2254:Journal of the American Chemical Society
2091:Journal of the American Chemical Society
1812:Journal of the American Chemical Society
1776:Journal of the American Chemical Society
1713:
1681:Journal of the American Chemical Society
1118:, substitutions have been reported with
945:
821:. Another method is reaction in diluted
333:with trapped molecules inside the cage.
3580:Liu, Y.; Yang, Y. W.; Chen, Y. (2005).
3261:Angewandte Chemie International Edition
3172:Angewandte Chemie International Edition
2184:Angewandte Chemie International Edition
2036:
2034:
2032:
2030:
2028:
2026:
2024:
1901:Angewandte Chemie International Edition
1535:and ethanol removed by evaporation; 50
1082:
637:
570:are used to indicate the ring-closed (
329:with substituents outside the cage and
4609:
2905:
2383:
2286:
1574:
1572:
1464:. DBU as it turns out only reacts to C
1393:elutes first with a purple color and C
542:
321:devoted to the chemical properties of
3631:
2732:N: Isoelectronic Heteroanalogues of C
2321:
1836:
1636:
1243:Buckminsterfullerene § Synthesis
1213:bucky dumbbell in the solid state by
4565:
2043:Encyclopedia of Inorganic Chemistry
2040:
2021:
1432:Experimental purification strategies
1217:(high-speed vibration milling) with
920:
900:
701:. However, completely hydrogenated C
4589:
1987:The Journal of Physical Chemistry A
1569:
1196:
1099:
964:. The organometallic chemistry of C
489:fullerene has 60 Ï electrons but a
13:
793:Fullerenes can be hydroxylated to
302:
14:
4633:
2623:The Journal of Physical Chemistry
2386:The Journal of Physical Chemistry
1507:from the insoluble mixture after
1444:was separated from a mixture of C
1308:through cyclodehydrogenation of C
1205:fullerene dimerizes in a formal
1036:, are structurally characterized.
788:
685:Examples of hydrofullerenes are C
665:
460:and a pentagon as a pentalene or
348:Chemical properties of fullerenes
4588:
4576:
4564:
4553:
4552:
3481:in the Undergraduate Laboratory"
3407:The Journal of Organic Chemistry
3207:The Journal of Organic Chemistry
2484:The Journal of Organic Chemistry
1936:The Journal of Organic Chemistry
1539:of Au/CD captures 5 mg of C
1460:to a solution of the mixture in
1426:X-ray photoelectron spectroscopy
1264:
980:-triene complexes are prepared.
873:predictions the as yet elusive C
610:. For example, the reaction of C
258:
246:
31:
3573:
3542:
3511:
3468:
3433:
3394:
3347:
3338:
3287:
3252:
3225:
3198:
3143:
3107:
3084:
3040:
2972:
2946:The Journal of Chemical Physics
2937:
2879:The Journal of Chemical Physics
2869:
2842:
2807:
2760:
2717:
2684:
2641:
2614:
2587:
2552:
2510:
2474:
2439:
2404:
2377:
2342:
2315:
2280:
2245:
2210:
2167:
2132:
2109:
2082:
2059:
1977:
1954:
1927:
1888:
1476:do not share this selectivity.
1326:
1274:polycyclic aromatic hydrocarbon
884:
724:
594:with a host of nucleophiles in
19:Part of a series of articles on
1863:
1830:
1802:
1762:
1707:
1664:
1646:Journal of Materials Chemistry
1630:
1606:"Covalent fullerene chemistry"
1597:
1334:is the process of obtaining a
1094:endohedral hydrogen fullerenes
1:
3917:Interface and colloid science
3671:Glossary of chemical formulae
3485:Journal of Chemical Education
3008:10.1126/science.269.5230.1554
2931:10.1016/S0965-9773(99)00301-3
2519:"There is a Hole in My Bucky"
2413:Journal of Chemical Education
2336:10.1016/S0040-4039(00)91828-8
1563:
1248:Multistep fullerene synthesis
1227:scanning tunneling microscopy
925:Fullerenes can be considered
2801:10.1016/0009-2614(92)80134-W
2710:10.1016/0040-4020(95)00361-B
2678:10.1016/0009-2614(95)01451-9
1236:
1073:solution in direct sunlight.
658:to a 5-membered ring is the
7:
4194:Bioorganometallic chemistry
3681:List of inorganic compounds
2596:Topics in Current Chemistry
2045:. Wiley. pp. 603â625.
1546:
1077:
857:as well. The reaction with
10:
4638:
4120:Dynamic covalent chemistry
4091:Enantioselective synthesis
4071:Physical organic chemistry
4024:Organolanthanide chemistry
1843:Pure and Applied Chemistry
1610:Pure and Applied Chemistry
1272:In the final step a large
1240:
1103:
1032:and , and the intercalate
949:
741:is a possible structure. C
598:. The intermediary formed
546:
491:closed shell configuration
351:
4548:
4451:
4212:
4128:
4049:
3999:
3875:
3818:
3709:Electroanalytical methods
3694:
3666:
1604:Diederich, F. N. (1997).
1280:at 1100 °C and 0.01
656:1,3-dipolar cycloaddition
632:Friedel-Crafts alkylation
342:carbon nanotube chemistry
4464:Nobel Prize in Chemistry
4380:Supramolecular chemistry
4019:Organometallic chemistry
2919:Nanostructured Materials
2836:10.1103/PhysRevB.60.1531
2781:Chemical Physics Letters
2658:Chemical Physics Letters
2448:Chemical Society Reviews
2141:Synthetic Communications
1553:Solubility of fullerenes
962:organometallic chemistry
622:. Fullerene reacts with
616:methylmagnesium chloride
235:Nanocrystalline material
211:Nanostructured materials
4402:Combinatorial chemistry
4313:Food physical chemistry
4276:Environmental chemistry
4160:Bioorthogonal chemistry
4086:Retrosynthetic analysis
3907:Chemical thermodynamics
3890:Spectroelectrochemistry
3833:Computational chemistry
3589:Chemical Communications
3520:Chemical Communications
3372:10.1021/acsnano.1c02222
3316:10.1126/science.1068427
3093:Chemical Communications
2608:10.1007/3-540-68117-5_3
1856:10.1351/pac198254051015
1740:10.1126/science.1095567
1623:10.1351/pac199769030395
1511:for several days. The C
915:sodium trichloroacetate
855:electrophilic additions
849:Electrophilic additions
438:orbital rehybridization
432:constitutes 80% of the
4474:of element discoveries
4320:Agricultural chemistry
4308:Carbohydrate chemistry
4199:Bioinorganic chemistry
4064:Alkane stereochemistry
4009:Coordination chemistry
3838:Mathematical chemistry
3704:Instrumental chemistry
3454:10.1002/chem.201303838
3184:10.1002/anie.201202777
3154:NH and Oxafulleroids C
2754:10.1002/anie.199522571
2196:10.1002/anie.201001280
1913:10.1002/anie.200700062
1462:1,2,3-trimethylbenzene
1332:Fullerene purification
1316:was reported in 2021.
1278:flash vacuum pyrolysis
1181:The fullerene oxides C
1053:fullerene reacts with
905:Fullerenes react with
608:organolithium reagents
596:nucleophilic additions
586:Nucleophilic additions
311:
4469:Timeline of chemistry
4366:Post-mortem chemistry
4351:Clandestine chemistry
4281:Atmospheric chemistry
4204:Biophysical chemistry
4036:Solid-state chemistry
3986:Equilibrium chemistry
3895:Photoelectrochemistry
2153:10.1081/SCC-200063958
1387:column chromatography
1286:carbon chlorine bonds
1055:tungsten hexacarbonyl
946:Fullerenes as ligands
891:retro-Bingel reaction
648:Diels-Alder reactions
354:Endohedral fullerenes
331:endohedral fullerenes
306:
265:Technology portal
60:Mechanical properties
4459:History of chemistry
4414:Chemical engineering
4189:Bioorganic chemistry
3939:Structural chemistry
3676:List of biomolecules
3246:10.1246/cl.2000.1016
3101:10.1039/CC9960001421
2851:Z. Anorg. Allg. Chem
2126:10.1039/C39930001784
2076:10.1039/C39920001791
1971:10.1039/P29960002079
1583:. Berlin: Springer.
1499:particles through a
1089:open-cage fullerenes
1083:Open-cage fullerenes
933:radical obtained by
895:retro-Prato reaction
853:Fullerenes react in
638:Pericyclic reactions
590:Fullerenes react as
327:exohedral fullerenes
230:Nanoporous materials
93:Buckminsterfullerene
4617:Geodesic polyarenes
4482:The central science
4436:Ceramic engineering
4361:Forensic toxicology
4334:Chemistry education
4232:Radiation chemistry
4214:Interdisciplinarity
4167:Medicinal chemistry
4105:Fullerene chemistry
3981:Microwave chemistry
3850:Molecular mechanics
3845:Molecular modelling
3567:10.1246/cl.2005.178
3497:2006JChEd..83.1218S
3448:(51): 17262â17266.
3308:2002Sci...295.1500S
3302:(5559): 1500â1503.
3123:(38): 12614â12615.
3062:1996Natur.383..147K
3000:1995Sci...269.1554H
2994:(5230): 1554â1556.
2958:1998JChPh.109.3425B
2891:1999JChPh.110.6927P
2828:1999PhRvB..60.1531O
2793:1992CPL...199..373C
2779:O. Dopeyball or ".
2670:1996CPL...249..399M
2635:10.1021/j100173a002
2538:10.1021/ja00131a024
2425:2003JChEd..80..799C
2398:10.1021/j100188a006
2324:Tetrahedron Letters
2103:10.1021/ja00066a014
1999:2006JPCA..110.8528T
1948:10.1021/jo00045a012
1824:10.1021/ja00071a080
1782:(43): 15093â15095.
1687:(35): 11352â11353.
1321:Stone Wales defects
998:coordination sphere
543:Fullerene reactions
315:Fullerene chemistry
132:Carbon quantum dots
4525:Chemical substance
4387:Chemical synthesis
4356:Forensic chemistry
4237:Actinide chemistry
4179:Clinical chemistry
3860:Molecular geometry
3855:Molecular dynamics
3810:Elemental analysis
3763:Separation process
3505:10.1021/ed083p1218
3366:(8): 12804â12814.
2925:(5â8): 1071â1076.
1837:Vogel, E. (1982).
1637:Prato, M. (1997).
1558:Geodesic polyarene
1489:inclusion compound
927:radical scavengers
777:, in which all 24
654:. An example of a
628:aluminium chloride
518:salt and then the
497:to form first the
389:and its relative C
364:soccer-ball-shaped
312:
253:Science portal
65:Optical properties
4604:
4603:
4540:Quantum mechanics
4505:Chemical compound
4488:Chemical reaction
4426:Materials science
4344:General chemistry
4339:Amateur chemistry
4267:Photogeochemistry
4252:Stellar chemistry
4222:Nuclear chemistry
4143:Molecular biology
4110:Polymer chemistry
4081:Organic synthesis
4076:Organic reactions
4041:Ceramic chemistry
4031:Cluster chemistry
3961:Chemical kinetics
3949:Molecular physics
3828:Quantum chemistry
3741:Mass spectrometry
3555:Chemistry Letters
3419:10.1021/jo7027008
3234:Chemistry Letters
3219:10.1021/jo981319t
3178:(25): 6163â6166.
3129:10.1021/ja805072h
2885:(14): 6927â6938.
2816:Physical Review B
2573:10.1021/cr050561e
2567:(12): 5191â5207.
2496:10.1021/jo070796l
2490:(17): 6526â6533.
2433:10.1021/ed080p799
2363:10.1021/cr300475r
2330:(43): 6911â6912.
2301:10.1021/cr3004955
2266:10.1021/ja0781590
2260:(12): 3985â3988.
2231:10.1021/nn700151z
2041:King, R. (2005).
2007:10.1021/jp0557971
1993:(27): 8528â8534.
1876:Organic Syntheses
1788:10.1021/ja108316e
1693:10.1021/ja063636k
1358:fullerene was by
1294:radical reactions
1258:organic synthesis
1219:potassium cyanide
952:Fullerene ligands
921:Radical additions
901:Carbene additions
831:hydrogen peroxide
811:potassium nitrate
757:, although only C
604:Grignard reagents
566:rules, the terms
478:values are 139.1
473:X-ray diffraction
469:aromatic compound
434:heat of formation
319:organic chemistry
301:
300:
113:Carbon allotropes
4629:
4592:
4591:
4580:
4568:
4567:
4556:
4555:
4500:Chemical element
4155:Chemical biology
4014:Magnetochemistry
3991:Mechanochemistry
3944:Chemical physics
3885:Electrochemistry
3790:Characterization
3652:
3645:
3638:
3629:
3628:
3623:
3622:
3620:
3619:
3613:
3607:. Archived from
3597:10.1039/b507650a
3586:
3577:
3571:
3570:
3546:
3540:
3539:
3528:10.1039/b611930a
3515:
3509:
3508:
3472:
3466:
3465:
3437:
3431:
3430:
3413:(7): 2931â2934.
3398:
3392:
3391:
3351:
3345:
3342:
3336:
3335:
3291:
3285:
3284:
3256:
3250:
3249:
3240:(9): 1016â1017.
3229:
3223:
3222:
3202:
3196:
3195:
3147:
3141:
3140:
3111:
3105:
3104:
3088:
3082:
3081:
3070:10.1038/383147a0
3044:
3038:
3037:
3019:
2985:
2976:
2970:
2969:
2966:10.1063/1.477410
2941:
2935:
2934:
2914:
2903:
2902:
2899:10.1063/1.478598
2873:
2867:
2866:
2846:
2840:
2839:
2811:
2805:
2804:
2764:
2758:
2757:
2721:
2715:
2714:
2712:
2688:
2682:
2681:
2645:
2639:
2638:
2618:
2612:
2611:
2591:
2585:
2584:
2561:Chemical Reviews
2556:
2550:
2549:
2523:
2514:
2508:
2507:
2478:
2472:
2471:
2460:10.1039/b913766a
2443:
2437:
2436:
2408:
2402:
2401:
2392:(9): 3576â3578.
2381:
2375:
2374:
2357:(7): 5262â5321.
2351:Chemical Reviews
2346:
2340:
2339:
2319:
2313:
2312:
2295:(9): 7209â7264.
2289:Chemical Reviews
2284:
2278:
2277:
2249:
2243:
2242:
2214:
2208:
2207:
2171:
2165:
2164:
2136:
2130:
2129:
2113:
2107:
2106:
2086:
2080:
2079:
2063:
2057:
2056:
2038:
2019:
2018:
1981:
1975:
1974:
1958:
1952:
1951:
1931:
1925:
1924:
1892:
1886:
1884:
1867:
1861:
1860:
1858:
1849:(5): 1015â1039.
1834:
1828:
1827:
1806:
1800:
1799:
1766:
1760:
1759:
1711:
1705:
1704:
1668:
1662:
1661:
1658:10.1039/a700080d
1652:(7): 1097â1109.
1643:
1634:
1628:
1627:
1625:
1601:
1595:
1594:
1576:
1440:In this method C
1268:
1215:mechanochemistry
1197:Fullerene dimers
1112:heterofullerenes
1100:Heterofullerenes
1007:, in which the C
823:sodium hydroxide
568:methanofullerene
538:
537:
536:
528:
527:
517:
516:
515:
507:
506:
413:and reportedly C
338:carbon nanotubes
293:
286:
279:
263:
262:
251:
250:
202:Titanium dioxide
41:Carbon nanotubes
35:
16:
15:
4637:
4636:
4632:
4631:
4630:
4628:
4627:
4626:
4607:
4606:
4605:
4600:
4544:
4447:
4441:Polymer science
4397:Click chemistry
4392:Green chemistry
4286:Ocean chemistry
4262:Biogeochemistry
4208:
4124:
4096:Total synthesis
4059:Stereochemistry
4045:
3995:
3912:Surface science
3902:Thermochemistry
3871:
3814:
3785:Crystallography
3690:
3662:
3656:
3626:
3617:
3615:
3611:
3591:(33): 4208â10.
3584:
3578:
3574:
3547:
3543:
3516:
3512:
3480:
3473:
3469:
3438:
3434:
3404:
3399:
3395:
3352:
3348:
3343:
3339:
3292:
3288:
3257:
3253:
3230:
3226:
3203:
3199:
3169:
3165:
3161:
3157:
3153:
3148:
3144:
3112:
3108:
3089:
3085:
3045:
3041:
2983:
2977:
2973:
2942:
2938:
2915:
2906:
2874:
2870:
2847:
2843:
2812:
2808:
2778:
2774:
2770:
2765:
2761:
2739:
2735:
2731:
2727:
2722:
2718:
2689:
2685:
2655:
2651:
2646:
2642:
2619:
2615:
2592:
2588:
2557:
2553:
2521:
2515:
2511:
2479:
2475:
2444:
2440:
2409:
2405:
2382:
2378:
2347:
2343:
2320:
2316:
2285:
2281:
2250:
2246:
2215:
2211:
2181:
2177:
2172:
2168:
2137:
2133:
2114:
2110:
2087:
2083:
2064:
2060:
2053:
2039:
2022:
1982:
1978:
1959:
1955:
1932:
1928:
1898:
1893:
1889:
1869:
1868:
1864:
1835:
1831:
1807:
1803:
1773:
1767:
1763:
1723:
1719:
1712:
1708:
1678:
1674:
1669:
1665:
1641:
1635:
1631:
1602:
1598:
1591:
1577:
1570:
1566:
1549:
1542:
1522:
1514:
1506:
1486:
1482:
1471:
1467:
1451:
1447:
1443:
1434:
1422:IR spectroscopy
1396:
1392:
1372:
1368:
1357:
1345:
1341:
1329:
1315:
1311:
1307:
1255:
1250:
1245:
1239:
1223:4-aminopyridine
1212:
1204:
1199:
1192:
1188:
1184:
1108:
1106:heterofullerene
1102:
1085:
1080:
1068:
1064:
1060:
1052:
1046:
1041:
1035:
1031:
1027:
1020:
1016:
1010:
1006:
990:
986:
967:
956:Fullerene is a
954:
948:
923:
911:dichlorocarbene
903:
887:
880:
876:
869:. According to
868:
864:
851:
840:
836:
820:
816:
791:
784:
776:
772:
768:
764:
760:
756:
752:
748:
744:
740:
736:
732:
727:
720:
716:
708:
704:
700:
696:
692:
688:
681:
677:
673:
668:
640:
620:Bingel reaction
613:
588:
580:methanoannulene
555:
549:Bingel reaction
545:
535:
532:
531:
530:
526:
523:
522:
521:
519:
514:
511:
510:
509:
505:
502:
501:
500:
498:
488:
458:cyclohexatriene
450:electronegative
420:
416:
412:
408:
404:
400:
396:
392:
388:
384:
375:Euler's theorem
371:
361:
356:
350:
310:
297:
257:
245:
142:Aluminium oxide
12:
11:
5:
4635:
4625:
4624:
4619:
4602:
4601:
4599:
4598:
4586:
4574:
4562:
4549:
4546:
4545:
4543:
4542:
4537:
4532:
4527:
4522:
4517:
4512:
4507:
4502:
4497:
4496:
4495:
4485:
4478:
4477:
4476:
4466:
4461:
4455:
4453:
4449:
4448:
4446:
4445:
4444:
4443:
4438:
4433:
4423:
4422:
4421:
4411:
4410:
4409:
4404:
4399:
4394:
4384:
4383:
4382:
4371:
4370:
4369:
4368:
4363:
4353:
4348:
4347:
4346:
4341:
4330:
4329:
4328:
4327:
4325:Soil chemistry
4317:
4316:
4315:
4310:
4303:Food chemistry
4300:
4298:Carbochemistry
4295:
4293:Clay chemistry
4290:
4289:
4288:
4283:
4272:
4271:
4270:
4269:
4264:
4254:
4248:Astrochemistry
4244:Cosmochemistry
4241:
4240:
4239:
4234:
4229:
4227:Radiochemistry
4218:
4216:
4210:
4209:
4207:
4206:
4201:
4196:
4191:
4186:
4184:Neurochemistry
4181:
4176:
4175:
4174:
4164:
4163:
4162:
4152:
4151:
4150:
4145:
4134:
4132:
4126:
4125:
4123:
4122:
4117:
4115:Petrochemistry
4112:
4107:
4102:
4093:
4088:
4083:
4078:
4073:
4068:
4067:
4066:
4055:
4053:
4047:
4046:
4044:
4043:
4038:
4033:
4028:
4027:
4026:
4016:
4011:
4005:
4003:
3997:
3996:
3994:
3993:
3988:
3983:
3978:
3976:Spin chemistry
3973:
3971:Photochemistry
3968:
3963:
3958:
3956:Femtochemistry
3953:
3952:
3951:
3941:
3936:
3931:
3926:
3925:
3924:
3914:
3909:
3904:
3899:
3898:
3897:
3892:
3881:
3879:
3873:
3872:
3870:
3869:
3868:
3867:
3857:
3852:
3847:
3842:
3841:
3840:
3830:
3824:
3822:
3816:
3815:
3813:
3812:
3807:
3802:
3797:
3792:
3787:
3782:
3781:
3780:
3775:
3768:Chromatography
3765:
3760:
3759:
3758:
3753:
3748:
3738:
3737:
3736:
3731:
3726:
3721:
3711:
3706:
3700:
3698:
3692:
3691:
3689:
3688:
3686:Periodic table
3683:
3678:
3673:
3667:
3664:
3663:
3655:
3654:
3647:
3640:
3632:
3625:
3624:
3572:
3541:
3510:
3478:
3467:
3432:
3402:
3393:
3346:
3337:
3286:
3267:(6): 969â972.
3251:
3224:
3197:
3167:
3163:
3159:
3155:
3151:
3142:
3106:
3083:
3039:
2971:
2936:
2904:
2868:
2857:(2): 175â177.
2841:
2806:
2776:
2772:
2768:
2759:
2737:
2733:
2729:
2725:
2716:
2683:
2653:
2649:
2640:
2613:
2586:
2551:
2509:
2473:
2454:(2): 817â844.
2438:
2403:
2376:
2341:
2314:
2279:
2244:
2225:(2): 327â333.
2209:
2190:(31): 5293â5.
2179:
2175:
2166:
2131:
2108:
2081:
2058:
2051:
2020:
1976:
1953:
1926:
1907:(19): 3513â6.
1896:
1887:
1862:
1829:
1801:
1771:
1761:
1721:
1717:
1706:
1676:
1672:
1663:
1629:
1616:(3): 395â400.
1596:
1589:
1567:
1565:
1562:
1561:
1560:
1555:
1548:
1545:
1540:
1520:
1512:
1504:
1497:colloidal gold
1484:
1480:
1469:
1465:
1449:
1445:
1441:
1433:
1430:
1394:
1390:
1370:
1366:
1355:
1343:
1339:
1328:
1325:
1313:
1309:
1305:
1298:chemical yield
1270:
1269:
1253:
1249:
1246:
1238:
1235:
1210:
1202:
1198:
1195:
1190:
1186:
1182:
1125:borafullerenes
1104:Main article:
1101:
1098:
1084:
1081:
1079:
1076:
1075:
1074:
1066:
1062:
1058:
1050:
1047:
1044:
1042:
1039:
1037:
1033:
1029:
1025:
1024:The solvated C
1022:
1018:
1014:
1012:
1008:
1004:
988:
984:
965:
950:Main article:
947:
944:
922:
919:
902:
899:
886:
883:
878:
874:
866:
862:
850:
847:
838:
834:
818:
814:
790:
789:Hydroxylations
787:
782:
774:
770:
766:
762:
758:
754:
750:
746:
745:reacts with Cl
742:
738:
734:
730:
726:
723:
718:
714:
706:
702:
698:
694:
690:
686:
679:
675:
671:
667:
666:Hydrogenations
664:
660:Prato reaction
644:cycloadditions
639:
636:
611:
587:
584:
582:) structures.
553:Prato reaction
544:
541:
533:
524:
512:
503:
486:
418:
414:
410:
406:
402:
398:
394:
390:
386:
382:
381:hexagons and C
369:
359:
358:Fullerene or C
349:
346:
340:is covered in
317:is a field of
308:
299:
298:
296:
295:
288:
281:
273:
270:
269:
268:
267:
255:
240:
239:
238:
237:
232:
227:
222:
214:
213:
207:
206:
205:
204:
199:
194:
189:
184:
179:
174:
169:
164:
159:
154:
149:
144:
139:
134:
126:
125:
118:
117:
116:
115:
110:
105:
100:
95:
87:
86:
80:
79:
78:
77:
72:
67:
62:
57:
52:
44:
43:
37:
36:
28:
27:
21:
20:
9:
6:
4:
3:
2:
4634:
4623:
4620:
4618:
4615:
4614:
4612:
4597:
4596:
4587:
4585:
4584:
4579:
4575:
4573:
4572:
4563:
4561:
4560:
4551:
4550:
4547:
4541:
4538:
4536:
4533:
4531:
4530:Chemical bond
4528:
4526:
4523:
4521:
4518:
4516:
4513:
4511:
4508:
4506:
4503:
4501:
4498:
4494:
4491:
4490:
4489:
4486:
4483:
4479:
4475:
4472:
4471:
4470:
4467:
4465:
4462:
4460:
4457:
4456:
4454:
4450:
4442:
4439:
4437:
4434:
4432:
4429:
4428:
4427:
4424:
4420:
4419:Stoichiometry
4417:
4416:
4415:
4412:
4408:
4405:
4403:
4400:
4398:
4395:
4393:
4390:
4389:
4388:
4385:
4381:
4378:
4377:
4376:
4375:Nanochemistry
4373:
4372:
4367:
4364:
4362:
4359:
4358:
4357:
4354:
4352:
4349:
4345:
4342:
4340:
4337:
4336:
4335:
4332:
4331:
4326:
4323:
4322:
4321:
4318:
4314:
4311:
4309:
4306:
4305:
4304:
4301:
4299:
4296:
4294:
4291:
4287:
4284:
4282:
4279:
4278:
4277:
4274:
4273:
4268:
4265:
4263:
4260:
4259:
4258:
4255:
4253:
4249:
4245:
4242:
4238:
4235:
4233:
4230:
4228:
4225:
4224:
4223:
4220:
4219:
4217:
4215:
4211:
4205:
4202:
4200:
4197:
4195:
4192:
4190:
4187:
4185:
4182:
4180:
4177:
4173:
4170:
4169:
4168:
4165:
4161:
4158:
4157:
4156:
4153:
4149:
4146:
4144:
4141:
4140:
4139:
4136:
4135:
4133:
4131:
4127:
4121:
4118:
4116:
4113:
4111:
4108:
4106:
4103:
4101:
4100:Semisynthesis
4097:
4094:
4092:
4089:
4087:
4084:
4082:
4079:
4077:
4074:
4072:
4069:
4065:
4062:
4061:
4060:
4057:
4056:
4054:
4052:
4048:
4042:
4039:
4037:
4034:
4032:
4029:
4025:
4022:
4021:
4020:
4017:
4015:
4012:
4010:
4007:
4006:
4004:
4002:
3998:
3992:
3989:
3987:
3984:
3982:
3979:
3977:
3974:
3972:
3969:
3967:
3964:
3962:
3959:
3957:
3954:
3950:
3947:
3946:
3945:
3942:
3940:
3937:
3935:
3934:Sonochemistry
3932:
3930:
3929:Cryochemistry
3927:
3923:
3922:Micromeritics
3920:
3919:
3918:
3915:
3913:
3910:
3908:
3905:
3903:
3900:
3896:
3893:
3891:
3888:
3887:
3886:
3883:
3882:
3880:
3878:
3874:
3866:
3863:
3862:
3861:
3858:
3856:
3853:
3851:
3848:
3846:
3843:
3839:
3836:
3835:
3834:
3831:
3829:
3826:
3825:
3823:
3821:
3817:
3811:
3808:
3806:
3803:
3801:
3800:Wet chemistry
3798:
3796:
3793:
3791:
3788:
3786:
3783:
3779:
3776:
3774:
3771:
3770:
3769:
3766:
3764:
3761:
3757:
3754:
3752:
3749:
3747:
3744:
3743:
3742:
3739:
3735:
3732:
3730:
3727:
3725:
3722:
3720:
3717:
3716:
3715:
3712:
3710:
3707:
3705:
3702:
3701:
3699:
3697:
3693:
3687:
3684:
3682:
3679:
3677:
3674:
3672:
3669:
3668:
3665:
3661:
3653:
3648:
3646:
3641:
3639:
3634:
3633:
3630:
3614:on 2016-03-04
3610:
3606:
3602:
3598:
3594:
3590:
3583:
3576:
3568:
3564:
3560:
3556:
3552:
3545:
3537:
3533:
3529:
3525:
3521:
3514:
3506:
3502:
3498:
3494:
3490:
3486:
3482:
3471:
3463:
3459:
3455:
3451:
3447:
3443:
3436:
3428:
3424:
3420:
3416:
3412:
3408:
3397:
3389:
3385:
3381:
3377:
3373:
3369:
3365:
3361:
3357:
3350:
3341:
3333:
3329:
3325:
3321:
3317:
3313:
3309:
3305:
3301:
3297:
3290:
3282:
3278:
3274:
3270:
3266:
3262:
3255:
3247:
3243:
3239:
3235:
3228:
3220:
3216:
3212:
3208:
3201:
3193:
3189:
3185:
3181:
3177:
3173:
3146:
3138:
3134:
3130:
3126:
3122:
3118:
3110:
3102:
3098:
3094:
3087:
3079:
3075:
3071:
3067:
3063:
3059:
3056:(6596): 147.
3055:
3051:
3043:
3035:
3031:
3027:
3023:
3018:
3013:
3009:
3005:
3001:
2997:
2993:
2989:
2982:
2975:
2967:
2963:
2959:
2955:
2951:
2947:
2940:
2932:
2928:
2924:
2920:
2913:
2911:
2909:
2900:
2896:
2892:
2888:
2884:
2880:
2872:
2864:
2860:
2856:
2852:
2845:
2837:
2833:
2829:
2825:
2821:
2817:
2810:
2802:
2798:
2794:
2790:
2786:
2782:
2763:
2755:
2751:
2747:
2743:
2720:
2711:
2706:
2702:
2698:
2694:
2687:
2679:
2675:
2671:
2667:
2663:
2659:
2644:
2636:
2632:
2628:
2624:
2617:
2609:
2605:
2601:
2597:
2590:
2582:
2578:
2574:
2570:
2566:
2562:
2555:
2547:
2543:
2539:
2535:
2531:
2527:
2520:
2513:
2505:
2501:
2497:
2493:
2489:
2485:
2477:
2469:
2465:
2461:
2457:
2453:
2449:
2442:
2434:
2430:
2426:
2422:
2418:
2414:
2407:
2399:
2395:
2391:
2387:
2380:
2372:
2368:
2364:
2360:
2356:
2352:
2345:
2337:
2333:
2329:
2325:
2318:
2310:
2306:
2302:
2298:
2294:
2290:
2283:
2275:
2271:
2267:
2263:
2259:
2255:
2248:
2240:
2236:
2232:
2228:
2224:
2220:
2213:
2205:
2201:
2197:
2193:
2189:
2185:
2170:
2162:
2158:
2154:
2150:
2146:
2142:
2135:
2127:
2123:
2119:
2112:
2104:
2100:
2096:
2092:
2085:
2077:
2073:
2069:
2062:
2054:
2052:9780470860786
2048:
2044:
2037:
2035:
2033:
2031:
2029:
2027:
2025:
2016:
2012:
2008:
2004:
2000:
1996:
1992:
1988:
1980:
1972:
1968:
1964:
1957:
1949:
1945:
1941:
1937:
1930:
1922:
1918:
1914:
1910:
1906:
1902:
1891:
1882:
1878:
1877:
1872:
1866:
1857:
1852:
1848:
1844:
1840:
1833:
1825:
1821:
1817:
1813:
1805:
1797:
1793:
1789:
1785:
1781:
1777:
1765:
1757:
1753:
1749:
1745:
1741:
1737:
1734:(5671): 699.
1733:
1729:
1725:
1710:
1702:
1698:
1694:
1690:
1686:
1682:
1667:
1659:
1655:
1651:
1647:
1640:
1633:
1624:
1619:
1615:
1611:
1607:
1600:
1592:
1590:3-540-64939-5
1586:
1582:
1575:
1573:
1568:
1559:
1556:
1554:
1551:
1550:
1544:
1538:
1534:
1530:
1526:
1518:
1510:
1502:
1498:
1494:
1490:
1477:
1475:
1463:
1459:
1455:
1439:
1429:
1427:
1423:
1419:
1415:
1411:
1407:
1403:
1402:sulfuric acid
1398:
1388:
1384:
1380:
1376:
1363:
1361:
1353:
1349:
1337:
1333:
1324:
1322:
1317:
1302:
1299:
1295:
1291:
1287:
1283:
1279:
1275:
1267:
1263:
1262:
1261:
1259:
1244:
1234:
1232:
1228:
1224:
1220:
1216:
1208:
1207:cycloaddition
1194:
1179:
1177:
1173:
1169:
1165:
1161:
1157:
1153:
1149:
1145:
1141:
1137:
1136:
1135:azafullerenes
1131:
1127:
1126:
1121:
1117:
1113:
1107:
1097:
1095:
1090:
1072:
1069:complex in a
1056:
1048:
1043:
1038:
1023:
1013:
1003:
1002:
1001:
999:
995:
981:
979:
975:
971:
963:
959:
953:
943:
940:
936:
932:
928:
918:
916:
912:
908:
898:
896:
892:
882:
872:
860:
856:
846:
844:
832:
828:
825:catalysed by
824:
812:
808:
807:sulfuric acid
804:
803:
798:
797:
786:
780:
722:
711:
683:
663:
661:
657:
653:
649:
646:for instance
645:
635:
633:
629:
625:
624:chlorobenzene
621:
617:
609:
605:
601:
597:
593:
592:electrophiles
583:
581:
577:
573:
569:
565:
560:
554:
550:
540:
496:
492:
483:
481:
477:
474:
470:
467:
463:
459:
453:
451:
447:
443:
439:
435:
431:
430:strain energy
427:
426:pyramidalized
422:
380:
376:
372:
365:
355:
345:
343:
339:
334:
332:
328:
324:
320:
316:
305:
294:
289:
287:
282:
280:
275:
274:
272:
271:
266:
261:
256:
254:
249:
244:
243:
242:
241:
236:
233:
231:
228:
226:
223:
221:
220:Nanocomposite
218:
217:
216:
215:
212:
209:
208:
203:
200:
198:
195:
193:
190:
188:
185:
183:
182:Ironâplatinum
180:
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127:
124:
123:nanoparticles
120:
119:
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109:
108:Health impact
106:
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101:
99:
98:C70 fullerene
96:
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25:Nanomaterials
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4569:
4557:
4407:Biosynthesis
4257:Geochemistry
4172:Pharmacology
4148:Cell biology
4138:Biochemistry
4104:
3966:Spectroscopy
3865:VSEPR theory
3714:Spectroscopy
3658:Branches of
3616:. Retrieved
3609:the original
3588:
3575:
3558:
3554:
3544:
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1487:forms a 1:2
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1373:starts with
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1327:Purification
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1290:free radical
1284:. The three
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1200:
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1116:spectroscopy
1111:
1109:
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1061:to the (ηÂČ-C
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885:Eliminations
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725:Halogenation
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572:cyclopropane
556:
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357:
335:
314:
313:
157:Cobalt oxide
137:Quantum dots
102:
70:Applications
4595:WikiProject
3820:Theoretical
3805:Calorimetry
3491:(8): 1218.
2952:(9): 3425.
2822:(3): 1531.
2697:Tetrahedron
1543:fullerene.
1406:nitric acid
1346:and higher
1028:compounds:
935:thermolysis
796:fullerenols
476:bond length
440:of the spÂČ
307:Fullerene C
4622:Fullerenes
4611:Categories
4431:Metallurgy
4130:Biological
3696:Analytical
3618:2015-08-29
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2602:: 93â134.
2419:(7): 799.
1883:: 80. 2006
1564:References
1517:filtration
1383:filtration
1375:extraction
1348:homologues
1288:served as
1241:See also:
1152:phosphorus
976:-diene or
939:photolysis
547:See also:
446:Ï orbitals
352:See also:
323:fullerenes
177:Iron oxide
84:Fullerenes
4493:Catalysis
4001:Inorganic
3795:Titration
3660:chemistry
3388:235074316
1525:adamantol
1509:refluxing
1483:but not C
1456:compound
1352:fullerene
1336:fullerene
1237:Synthesis
1231:monolayer
1148:germanium
994:hapticity
871:in silico
802:fullerols
600:carbanion
576:fullerene
495:potassium
462:radialene
147:Cellulose
103:Chemistry
55:Chemistry
50:Synthesis
4559:Category
4515:Molecule
4452:See also
3877:Physical
3605:16100605
3536:17252112
3462:24273113
3427:18321126
3380:34018713
3360:ACS Nano
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3281:12491284
3192:22573566
3137:18759401
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2371:23570603
2309:23773169
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2219:ACS Nano
2204:20575126
2161:96782160
2015:16821837
1921:17385815
1796:20931962
1756:39189162
1748:15118154
1701:16939248
1547:See also
1529:recycled
1418:carboxyl
1414:carbonyl
1410:hydroxyl
1130:nitrogen
1078:Variants
907:carbenes
893:and the
843:hydroxyl
769:yields C
442:orbitals
225:Nanofoam
192:Platinum
75:Timeline
4571:Commons
4535:Alchemy
4051:Organic
3493:Bibcode
3304:Bibcode
3296:Science
3078:4315682
3058:Bibcode
2996:Bibcode
2988:Science
2954:Bibcode
2887:Bibcode
2824:Bibcode
2789:Bibcode
2728:N and C
2666:Bibcode
2652:B and C
2421:Bibcode
1995:Bibcode
1774:Cage".
1728:Science
1533:ethanol
1454:amidine
1379:toluene
1296:. The
1185:O and C
1176:iridium
1172:rhodium
1156:silicon
1144:arsenic
931:t-butyl
859:bromine
779:bromine
652:benzyne
471:. The
152:Ceramic
4583:Portal
3729:UV-Vis
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1438:et al.
1209:to a C
1168:nickel
1164:copper
1140:oxygen
1071:hexane
1065:)W(CO)
958:ligand
559:strain
197:Silver
162:Copper
121:Other
3756:MALDI
3724:Raman
3612:(PDF)
3585:(PDF)
3384:S2CID
3332:74269
3328:S2CID
3162:and C
3074:S2CID
3030:S2CID
2984:(PDF)
2736:and C
2542:S2CID
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2157:S2CID
1752:S2CID
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1017:has C
987:and C
693:and C
630:in a
614:with
564:IUPAC
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187:Lipid
4510:Atom
3778:HPLC
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3458:PMID
3423:PMID
3376:PMID
3320:PMID
3277:PMID
3188:PMID
3133:PMID
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2367:PMID
2305:PMID
2270:PMID
2235:PMID
2200:PMID
2178:(OH)
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2011:PMID
1917:PMID
1792:PMID
1744:PMID
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817:(OH)
813:to C
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