20:
36:
535:, endohedral fullerenes represent an atomic trap that is stable at room temperature and for an arbitrarily long time. Atomic or ion traps are of great interest since particles are present free from (significant) interaction with their environment, allowing unique quantum mechanical phenomena to be explored. For example, the compression of the atomic
130:
regardless of whether M was inside or outside the fullerene. In order to allow for more detailed discussions with minimal loss of information, a more explicit notation was proposed in 1991, where the atoms listed to the left of the @ sign are situated inside the network composed of the atoms listed
1099:
Saunders, Martin; Jimenez-Vazquez, Hugo A.; Cross, R. James; Mroczkowski, Stanley; Gross, Michael L.; Giblin, Daryl E.; Poreda, Robert J. (1994). "Incorporation of helium, neon, argon, krypton, and xenon into fullerenes using high pressure".
325:
which is better described as @. These anionic fullerene cages are very stable molecules and do not have the reactivity associated with ordinary empty fullerenes. They are stable in air up to very high temperatures (600 to 850 °C).
886:
Yamada, M; Nakahodo, T; Wakahara, T; Tsuchiya, T; Maeda, Y; Akasaka, T; Kako, M; Yoza, K; Horn, E; Mizorogi, N; Kobayashi, K; Nagase, S (2005). "Positional control of encapsulated atoms inside a fullerene cage by exohedral addition".
277:
and coworkers, the inclusion of a molecule fragment in a fullerene cage had succeeded for the first time. This compound can be prepared by arc-vaporization at temperatures up to 1100 °C of graphite rods packed with
704:) may lead to dissociation of the encapsulated molecules and reaction of their fragments with interiors of the fullerene cage. Such reactions should result in endohedral fullerene adducts, which are currently unknown.
1657:
Sabirov, Denis (2013). "From
Endohedral Complexes to Endohedral Fullerene Covalent Derivatives: A Density Functional Theory Prognosis of Chemical Transformation of Water Endofullerene H2O@C60 upon Its Compression".
296:
Endohedral metallofullerenes are characterised by the fact that electrons will transfer from the metal atom to the fullerene cage and that the metal atom takes a position off-center in the cage. The size of the
1351:
Langlet, R.; Mayer, A.; Geuquet, N.; Amara, H.; Vandescuren, M.; Henrard, L.; Maksimenko, S.; Lambin, Ph. (2007). "Study of the polarizability of fullerenes with a monopole–dipole interaction model".
652:
fullerene as a
Faraday cage, which isolates the encapsulated atom from the external electric field. The mentioned relations should be typical for the more complicated endohedral structures (e.g., C
696:. The encapsulated molecules display unusual physical properties which have been studied by a variety of physical methods. As shown theoretically, compression of molecular endofullerenes (e.g., H
787:
Chai, Yan; Guo, Ting; Jin, Changming; Haufler, Robert E.; Chibante, L. P. Felipe; Fure, Jan; Wang, Lihong; Alford, J. Michael; Smalley, Richard E. (1991). "Fullerenes wlth Metals Inside".
250:
and as different isomer cages. Aside from the dominant presence of mono-metal cages, numerous di-metal endohedral complexes and the tri-metal carbide fullerenes like Sc
737:
Gimenez-Lopez, Maria del Carmen; Chuvilin, Andrey; Kaiser, Ute; Khlobystov, Andrei N. (2010). "Functionalised endohedral fullerenes in single-walled carbon nanotubes".
627:
601:
546:
Contrary to the metallo endohedral compounds, these complexes cannot be produced in an arc. Atoms are implanted in the fullerene starting material using
158:
The choice of the symbol has been explained by the authors as being concise, readily printed and transmitted electronically (the at sign is included in
573:
do not equal to the sum of polarizabilities of a fullerene cage and the trapped atom, i.e. exaltation of polarizability occurs.,. The sign of the Δ
364:
are equal the two encapsulated Ce atoms exhibit a three-dimensional random motion. This is evidenced by the presence of only two signals in the C-
1266:
333:
is utilised in a method to purify compounds from a complex mixture of empty and partly filled fullerenes of different cage size. In this method
817:
Ge, Z; Duchamp, Jc; Cai, T; Gibson, Hw; Dorn, Hc (2005). "Purification of endohedral trimetallic nitride fullerenes in a single, facile step".
1230:
Yan, Hong; Yu, Shengping; Wang, Xin; He, Yang; Huang, Wen; Yang, Mingli (2008). "Dipole polarizabilities of noble gas endohedral fullerenes".
162:, which most modern character encoding schemes are based on), and the visual aspects suggesting the structure of an endohedral fullerene.
668:
Closed fullerenes encapsulating small molecules have been synthesized. Representative are the synthesis of the dihydrogen endofullerene H
924:"Molecular mechanism of pancreatic tumor metastasis inhibition by Gd@C82(OH)22 and its implication for de novo design of nanomedicine"
1707:
543:. The nitrogen atom can be used as a probe, in order to detect the smallest changes of the electronic structure of its environment.
540:
629:), it is negative (depression of polarizability). The following formula, describing the dependence of Δα on n, has been proposed: Δ
569:
Noble gas endofullerenes are predicted to exhibit unusual polarizability. Thus, calculated values of mean polarizability of Ng@C
47:
peapods. Metal atoms (M = Ho or Sc) are seen as dark spots inside the fullerene molecules; they are doubly encapsulated in the C
983:"Non-destructive inhibition of metallofullerenol Gd@C(82)(OH)(22) on WW domain: implication on signal transduction pathway"
555:
98:) in the name reflects the notion of a small molecule trapped inside a shell. Two types of endohedral complexes exist:
516:, which are observed very easily with the endohedral metallofullerenes, could only be observed in the case of the N@C
1038:
Saunders, M.; Jiménez-Vázquez, H. A.; Cross, R. J.; Poreda, R. J. (1993). "Stable compounds of helium and neon. He@C
365:
922:
Kang SG, Zhou G, Yang P, Liu Y, Sun B, Huynh T, Meng H, Zhao L, Xing G, Chen C, Zhao Y, Zhou R (September 2012).
855:
K.Muthukumar; J.A.Larsson (2008). "Explanation of the different preferential binding sites for Ce and La in M2@C
338:
463:
compound was also demonstrated with pressures of 3 kbars and incorporation of up to 0.1% of the noble gases.
509:
298:
577:
polarizability exaltation depends on the number of atoms in a fullerene molecule: for small fullerenes (
532:
369:
342:
562:
methods. A recent example of endohedral fullerenes includes single molecules of water encapsulated in C
175:
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238:. The synthesis in the arc reactor is however unspecific. Besides unfilled fullerenes, endohedral
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Philosophical
Transactions of the Royal Society A: Mathematical, Physical and Engineering Sciences
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1423:
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1165:
1081:
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The central atom in these endohedral complexes is located in the center of the cage. While other
404:
91:
1386:
Komatsu, K.; Murata, M.; Murata, Y. (2005). "Encapsulation of
Molecular Hydrogen in Fullerene C
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Kurotobi, Kei; Murata, Yasujiro (2012). "A Single
Molecule of Water Encapsulated in Fullerene C
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is sufficiently stable that exohedral derivatization from the mono- to the hexa adduct of the
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spectrum. It is possible to force the metal atoms to a standstill at the equator as shown by
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of the nitrogen atom in the center to the carbon atoms of the cage takes place. Therefore,
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are chemically very inert and commonly exist as individual atoms, this is not the case for
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the two metal atoms exhibit a non-bonded interaction. Since all the six-membered rings in C
341:
resin and used as a solid phase against a mobile phase containing the complex mixture in a
302:
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1441:
Kurotobi, K.; Murata, Y. (2011). "A Single
Molecule of Water Encapsulated in Fullerene C
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Zope, Rajendra R (2008). "Electronic structure and static dipole polarizability of C
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operation. Only very stable fullerenes such as @ pass through the column unreacted.
19:
1688:
Movie "Helium atom trapped in fullerene (C60) and dodecahedrane (C20H20)" (Youtube)
499:
282:
215:
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1183:
Sabirov, D.; Bulgakov, R. (2010). "Polarizability exaltation of endofullerenes X@C
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in a noble-gas atmosphere. Under these conditions about one out of every 650,000 C
16:
Fullerene molecule with additional atoms, ions, or clusters enclosed within itself
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502:
223:
191:
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Proceedings of the
National Academy of Sciences of the United States of America
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is more surprising. The nitrogen atom is in its electronic initial state (S
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endofullerenes with sufficient accuracy. The calculated data allows using C
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when the fullerene is exahedrally functionalized by an electron donation
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35:
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is not always simple to determine. In most cases it is between 2 and 3
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In 1999 a discovery drew large attention. With the synthesis of the Sc
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as a consequence of the packing in the cage could be observed with
644:−1). It describes the DFT-calculated mean polarizabilities of Ng@C
505:
456:
448:
159:
155:
trapped inside, and two potassium atoms adhering to the outside."
144:
34:
18:
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in a high resolution spectrum as shoulders of the central line.
444:
400:
395:, an endohedral metallofluorenol, can competitively inhibit the
290:
170:
Doping fullerenes with electropositive metals takes place in an
135:
if M were inside the carbon network. A more complex example is K
67:
202:. Also possible are endohedral complexes with elements of the
71:
384:
with 1,1,2,2-tetrakis(2,4,6-trimethylphenyl)-1,2-disilirane.
1318:
Journal of
Physics B: Atomic, Molecular and Optical Physics
1187:(n = 20, 24, 28, 36, 50, and 60; X is a noble gas atom)".
131:
to the right. The example above would then be denoted M@C
558:
can be produced by opening and closing a fullerene by
609:
583:
143:
B), which denotes "a 60-atom fullerene cage with one
478:
and so the formation of the endohedral complexes N@C
403:from activating. It was originally developed as an
621:
595:
439:atom. The formation of endohedral complexes with
550:(nitrogen and phosphorus complexes) or by direct
23:Rendering of a buckminsterfullerene containing a
1610:"Spectroscopy of light-molecule endofullerenes"
126:) with an atom (M) was simply represented as MC
78:enclosed within their inner spheres. The first
8:
1548:"First Synthesis and Characterization of CH
660:and giant fullerene-containing "onions" ).
494:) and is highly reactive. Nevertheless, N@C
242:develop with different cage sizes like La@C
684:, the hydrogen fluoride endofullerene HF@C
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1571:
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957:
947:
782:
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778:
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608:
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1496:Krachmalnicoff, A.; et al. (2016).
889:Journal of the American Chemical Society
819:Journal of the American Chemical Society
812:
810:
603:), it is positive; for the larger ones (
1560:Angewandte Chemie International Edition
729:
459:as well as numerous adducts of the He@C
850:
848:
7:
1546:Bloodworth, S.; et al. (2019).
508:is possible. In these compounds no
1498:"The dipolar endofullerene HF@C60"
1265:Delaney, P.; Greer, J. C. (2004).
688:, and the methane endofullerene CH
151:in the geodesic network, a single
14:
981:Kang SG, Huynh T, Zhou R (2012).
527:require complex equipment, e.g.
289:in a nitrogen atmosphere at 300
313:however it can be even about 6
51:molecules and in the nanotubes.
39:Electron microscopy images of M
861:Journal of Materials Chemistry
556:endohedral hydrogen fullerenes
423:are prepared by pressurizing C
1:
1373:10.1016/j.diamond.2007.10.019
1338:10.1088/0953-4075/41/8/085101
1070:10.1126/science.259.5100.1428
789:Journal of Physical Chemistry
1252:10.1016/j.cplett.2008.03.046
305:units, in the case of the La
166:Endohedral metallofullerenes
100:endohedral metallofullerenes
676:, the water endofullerene H
1724:
411:Non-metal doped fullerenes
329:The lack of reactivity in
104:non-metal doped fullerenes
1209:10.1134/S0021364010220054
415:Endohedral complexes He@C
376:group in a reaction of Ce
285:and graphite powder in a
1708:Supramolecular chemistry
1232:Chemical Physics Letters
664:Molecular endofullerenes
1467:10.1126/science.1206376
1412:10.1126/science.1106185
1390:by Organic Synthesis".
1275:Applied Physics Letters
1154:10.1126/science.1206376
949:10.1073/pnas.1204600109
622:{\displaystyle n>30}
596:{\displaystyle n<30}
435:cages was doped with a
147:atom substituted for a
1635:10.1098/rsta.2012.0429
1573:10.1002/anie.201900983
623:
597:
52:
32:
624:
598:
370:x-ray crystallography
343:column chromatography
331:Diels-Alder reactions
204:alkaline earth metals
66:that have additional
56:Endohedral fullerenes
38:
22:
1353:Diamond Relat. Mater
607:
581:
262:were also isolated.
178:. The metals can be
120:buckminsterfullerene
1626:2013RSPTA.37120429L
1517:2016NatCh...8..953K
1459:2011Sci...333..613K
1404:2005Sci...307..238K
1365:2007DRM....16.2145L
1330:2008JPhB...41h5101Z
1287:2004ApPhL..84..431D
1244:2008CPL...456..223Y
1201:2010JETPL..92..662S
1146:2011Sci...333..613K
1115:10.1021/ja00084a089
1062:1993Sci...259.1428S
1056:(5100): 1428–1430.
999:2012NatSR...2E.957K
940:2012PNAS..10915431K
801:10.1021/j100173a002
719:Inclusion compounds
280:scandium(III) oxide
86:complex called La@C
1620:(1998): 20120429.
1525:10.1038/nchem.2563
1271:as a Faraday cage"
987:Scientific Reports
751:10.1039/C0CC02929G
619:
593:
541:ENDOR spectroscopy
405:MRI contrast agent
53:
33:
1672:10.1021/jp310673j
1566:(15): 5038–5043.
1453:(6042): 613–616.
1398:(5707): 238–240.
1359:(12): 2145–2149.
1295:10.1063/1.1640783
1103:J. Am. Chem. Soc.
1007:10.1038/srep00957
901:10.1021/ja054346r
831:10.1021/ja055089t
795:(20): 7564–7568.
714:Fullerene ligands
560:organic chemistry
554:. Alternatively,
337:is modified as a
240:metallofullerenes
180:transition metals
176:laser evaporation
114:In a traditional
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1675:
1666:(2): 1178–1182.
1660:J. Phys. Chem. C
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552:ion implantation
399:in the oncogene
339:cyclopentadienyl
335:Merrifield resin
116:chemical formula
94:in 1985. The @ (
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859:(M = Ce, La)".
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