Fullerene

Model of the C60 fullerene (buckminsterfullerene).

Model of the C20 fullerene.

Model of a carbon nanotube.

C60 fullerite (bulk solid C60).

A fullerene is an allotrope of carbon

whose molecule consists of carbon atoms
connected by single and double bonds so
as to form a closed or partially closed
mesh, with fused rings of five to seven
atoms. The molecule may be a hollow
sphere, ellipsoid, tube, or many other
shapes and sizes. Graphene (isolated
atomic layers of graphite), which is a flat
mesh of regular hexagonal rings, can be
seen as an extreme member of the family.

Fullerenes with a closed mesh topology

are informally denoted by their empirical
formula Cn, often written Cn, where n is the
number of carbon atoms. However, for
some values of n there maybe more than
one isomer.

The family is named after

buckminsterfullerene (C60), the most
famous member, which in turn is named
after Buckminster Fuller. The closed
fullerenes, especially C60, are also
informally called buckyballs for their
obvious resemblance to the standard ball
of association football ("soccer"). Nested
closed fullerenes have been named bucky
onions. Cylindrical fullerenes are also
called carbon nanotubes or buckytubes.
The bulk solid form of pure or mixed
fullerenes is called fullerite.

Fullerenes had been predicted for some

time, but only after their accidental
synthesis in 1985 were they detected in
nature [1][2] and outer space.[3][4] The
discovery of fullerenes greatly expanded
the number of known allotropes of carbon,
which had previously been limited to
graphite, diamond, and amorphous carbon
such as soot and charcoal. They have
been the subject of intense research, both
for their chemistry and for their
technological applications, especially in
materials science, electronics, and
nanotechnology.[5]

History

The icosahedral fullerene C540, another member of

the family of fullerenes

Predictions and limited

observations
The icosahedral C60H60 cage was
mentioned in 1965 as a possible
topological structure.[6] Eiji Osawa
currently of Toyohashi University of
Technology predicted the existence of C60
in 1970.[7][8] He noticed that the structure
of a corannulene molecule was a subset of
the shape of a soccer ball, and
hypothesised that a full ball shape could
also exist. Japanese scientific journals
reported his idea, but neither it nor any
translations of it reached Europe or the
Americas.

Also in 1970, R. W. Henson (then of the UK

Atomic Energy Research Establishment)
proposed the C60 structure and made a
model of it. Unfortunately, the evidence for
that new form of carbon was very weak at
the time, so the proposal and was met
with skepticism, and was never published.
It was acknowledged only in 1999.[9][10]

In 1973, independently from Henson, a

group of scientists from the USSR made a
quantum-chemical analysis of the stability
of C60 and calculated its electronic
structure. The paper was published in
1973,[11] but the scientific community did
not give much importance to this
theoretical prediction.
Around 1980, Sumio Iijima identified the
molecule of C60 from an electron
microscope image of carbon black, where
it formed the core of a particle with the
structure of a "bucky onion".[12]

Discovery of C60

In 1985 Harold Kroto of the University of

Sussex, working with James R. Heath,
Sean O'Brien, Robert Curl and Richard
Smalley from Rice University, discovered
fullerenes in the sooty residue created by
vaporising carbon in a helium atmosphere.
In the mass spectrum of the product,
discrete peaks appeared corresponding to
molecules with the exact mass of sixty or
seventy or more carbon atoms, namely C60
and C70. The team identified their structure
as the now familiar "buckyballs".[13]

The name "buckminsterfullerene" was

eventually chosen for C60 by the
discoverers as an homage to American
architect Buckminster Fuller for the vague
similarity of the structure to the geodesic
domes which he popularized; which, if they
were extended to a full sphere, would also
have the icosahedral symmetry group.[14]
The "ene" ending was chosen to indicate
that the carbons are unsaturated, being
connected to only three other atoms
instead of the normal four. The shortened
named "fullerene" eventually came to be
applied to the whole family.

Kroto, Curl, and Smalley were awarded the

1996 Nobel Prize in Chemistry[15] for their
roles in the discovery of this class of
molecules.

Further developments

Kroto and the Rice team already

discovered other fullerenes besides
C60,[13] and the list was much expanded in
the following years. Carbon nanotubes
were first discovered and synthesized in
1991.[16][17]

After their discovery, minute quantities of

fullerenes were found to be produced in
sooty flames, and by lightning discharges
in the atmosphere.[2] In 1992, fullerenes
were found in a family of minerals known
as shungites in Karelia, Russia.[1].

The production techniques were improved

by many scientists, including Donald
Huffman, Wolfgang Krätschmer, Lowell D.
Lamb, and Konstantinos Fostiropoulos.
Thanks to their efforts, by 1990 it was
relatively easy to produce gram-sized
samples of fullerene powder. Fullerene
purification remains a challenge to
chemists and to a large extent determines
fullerene prices.

In 2010, the spectral signatures of C60 and

C70 were observed by NASA's Spitzer
infrared telescope in a cloud of cosmic
dust surrounding a star 6500 light years
away.[3] Kroto commented: "This most
exciting breakthrough provides convincing
evidence that the buckyball has, as I long
suspected, existed since time immemorial
in the dark recesses of our galaxy."[4]
According to astronomer Letizia
Stanghellini, "It’s possible that buckyballs
from outer space provided seeds for life
on Earth."[18] In 2019, ionized C60
molecules were detected with the Hubble
Space Telescope in the space between
those stars.[19][20]

Types
There are two major families of fullerenes,
with fairly distinct properties and
applications: the closed buckyballs and
the open-ended cylindrical carbon
nanotubes.[21] However, hybrid structures
exist between those two classes, such as
carbon nanobuds — nanotubes capped by
hemispherical meshes or larger
"buckybuds".

Buckyballs

upright=0.5C60 with isosurface of ground state

electron density as calculated with DFT
Rotating view of C60, one kind of fullerene

Buckminsterfullerene

Buckminsterfullerene is the smallest

fullerene molecule containing pentagonal
and hexagonal rings in which no two
pentagons share an edge (which can be
destabilizing, as in pentalene). It is also
most common in terms of natural
occurrence, as it can often be found in
soot.
The structure of C60 is a truncated
icosahedron, which resembles an
association football ball of the type made
of twenty hexagons and twelve pentagons,
with a carbon atom at the vertices of each
polygon and a bond along each polygon
edge.

The van der Waals diameter of a C60

molecule is about 1.1 nanometers (nm).[22]
The nucleus to nucleus diameter of a C60
molecule is about 0.71 nm.

The C60 molecule has two bond lengths.

The 6:6 ring bonds (between two
hexagons) can be considered "double
bonds" and are shorter than the 6:5 bonds
(between a hexagon and a pentagon). Its
average bond length is 1.4 angstroms.

Other buckyballs

Another fairly common fullerene is C70,[23]

but fullerenes with 72, 76, 84 and even up
to 100 carbon atoms are commonly
obtained.

The smallest fullerene is the dodecahedral

C20. There are no fullerenes with 22
vertices.[24] The number of fullerenes C2n
grows with increasing n = 12, 13, 14, ...,
roughly in proportion to n9 (sequence
A007894 in the OEIS). For instance, there
are 1812 non-isomorphic fullerenes C60.
Note that only one form of C60, the
buckminsterfullerene alias truncated
icosahedron, has no pair of adjacent
pentagons (the smallest such fullerene).
To further illustrate the growth, there are
214,127,713 non-isomorphic fullerenes
C200, 15,655,672 of which have no
adjacent pentagons. Optimized structures
of many fullerene isomers are published
and listed on the web.[25]

Heterofullerenes have heteroatoms

substituting carbons in cage or tube-
shaped structures. They were discovered
in 1993[26] and greatly expand the overall
fullerene class of compounds. Notable
examples include boron, nitrogen
(azafullerene), oxygen, and phosphorus
derivatives.

Trimetasphere carbon nanomaterials were

discovered by researchers at Virginia Tech
and licensed exclusively to Luna
Innovations. This class of novel molecules
comprises 80 carbon atoms (C80) forming
a sphere which encloses a complex of
three metal atoms and one nitrogen atom.
These fullerenes encapsulate metals
which puts them in the subset referred to
as metallofullerenes. Trimetaspheres have
the potential for use in diagnostics (as
safe imaging agents), therapeutics[27] and
in organic solar cells.[28]

Carbon nanotubes

This rotating model of a carbon nanotube shows its

3D structure.

Carbon nanotubes are cylindrical

fullerenes. These tubes of carbon are
usually only a few nanometres wide, but
they can range from less than a
micrometer to several millimeters in
length. They often have closed ends, but
can be open-ended as well. There are also
cases in which the tube reduces in
diameter before closing off. Their unique
molecular structure results in
extraordinary macroscopic properties,
including high tensile strength, high
electrical conductivity, high ductility, high
heat conductivity, and relative chemical
inactivity (as it is cylindrical and "planar" —
that is, it has no "exposed" atoms that can
be easily displaced). One proposed use of
carbon nanotubes is in paper batteries,
developed in 2007 by researchers at
Rensselaer Polytechnic Institute.[29]
Another highly speculative proposed use
in the field of space technologies is to
produce high-tensile carbon cables
required by a space elevator.

Derivatives
Buckyballs and carbon nanotubes have
been used as building blocks for a great
variety of derivatives and larger structures,
such as [21]

Nested buckyballs ("carbon nano-

onions" or "buckyonions")[30]proposed
for lubricants;[31]
 Nested carbon nanotubes ("carbon
megatubes")[32]
Linked "ball-and-chain" dimers (two
buckyballs linked by a carbon chain)[33]
Rings of buckyballs linked together.[34]

Heterofullerenes and non-

carbon fullerenes
After the discovery of C60, many
fullerenes have been synthesized (or
studied theoretically by molecular
modeling methods) in which some or all
the carbon atoms are replaced by other
elements. Inorganic nanotubes, in
particular, have attracted much attention.
Silicon

Silicon buckyballs have been created

around metal ions.

Boron

A type of buckyball which uses boron

atoms, instead of the usual carbon, was
predicted and described in 2007. The B80
structure, with each atom forming 5 or 6
bonds, is predicted to be more stable than
the C60 buckyball.[35] One reason for this
given by the researchers is that B80 is
actually more like the original geodesic
dome structure popularized by
Buckminster Fuller, which uses triangles
rather than hexagons. However, this work
has been subject to much criticism by
quantum chemists[36][37] as it was
concluded that the predicted Ih symmetric
structure was vibrationally unstable and
the resulting cage undergoes a
spontaneous symmetry break, yielding a
puckered cage with rare Th symmetry
(symmetry of a volleyball).[36] The number
of six-member rings in this molecule is 20
and number of five-member rings is 12.
There is an additional atom in the center of
each six-member ring, bonded to each
atom surrounding it. By employing a
systematic global search algorithm, later it
was found that the previously proposed
B80 fullerene is not global minimum for 80
atom boron clusters and hence can not be
found in nature.[38] In the same paper by
Sandip De et al., it was concluded that
boron's energy landscape is significantly
different from other fullerenes already
found in nature hence pure boron
fullerenes are unlikely to exist in nature.

Other elements

Inorganic (carbon-free) fullerene-type

structures have been built with the
disulfides of molibdenum (MoS2), long
used as a graphite-like lubricant, tungsten
(WS2), titanium (TiS2) and niobium (NbS2).
These materials were found to be stable
up to at least 350 tons/cm2 (34.3 GPa).[39]

Main fullerenes
Below is a table of main closed carbon
fullerenes synthesized and characterized
so far, with their CAS number when
known.[40] Fullerenes with fewer than 60
carbon atoms have been called "lower
fullerenes", and those with more than 70
atoms "higher fullerenes".
 Num. Mol. Cryst. Space Pearson
Formula No a (nm) b (nm) c (nm) β° Z
Isom. Symm. Symm. group symbol

C20 1 Ih

C60 1 Ih

C70 1 D5h

C72 1 D6h

C74 1 D3h

Monoclinic P21 4 mP2 1.102 1.108 1.768 108.10 2

C76 2 D2*
Cubic Fm3m 225 cF4 1.5475 1.5475 1.5475 90 4

C78 5 D2v

C80 7

C2,
C82 9 C2v, Monoclinic P21 4 mP2 1.141 1.1355 1.8355 108.07 2
C3v

D2*,
C84 24 Cubic Fm3m 1.5817[41] 1.5817 1.5817 90
D2d

C86 19

C88 35

C90 46

C3996

In the table, "Num.Isom." is the number of

possible isomers within the "isolated
pentagon rule", which states that two
pentagons in a fullerene should not share
edges.[42] "Mol.Symm." is the symmetry of
the molecule,[43][44], whereas
"Cryst.Symm." is that of the crstalline
framework in the solid state. Both are
specified for the most experimentally
abundant form(s). The asterisk * marks
symmetries with more than one chiral
form.

When C76 or C82 crystals are grown from

toluene solution they have a monoclinic
symmetry. The crystal structure contains
toluene molecules packed between the
spheres of the fullerene. However,
evaporation of the solvent from C76
transforms it into a face-centered cubic
form.[45] Both monoclinic and face-
centered cubic (fcc) phases are known for
better-characterized C60 and
C70fullerenes.

Properties
Topology

Schlegel diagrams are often used to clarify

the 3D structure of closed-shell fullerenes,
as 2D projections are often not ideal in this
sense.[46]

In mathematical terms, the combinatorial

topology (that is, the carbon atoms and
the bonds between them, ignoring their
positions and distances) of a closed-shell
fullerene with a simple sphere-like mean
surface (orientable, genus zero)can be
represented as a convex polyhedron; more
precisely, its one-dimensional skeleton,
consisting of its vertices and edges. The
Schlegel diagram is a projection of that
skeleton onto one of the faces of the
polyhedron, through a point just outside
that face; so that all other vertices project
inside that face.

Schlegel diagrams of some fullerenes

 C20
(dodecahedron)

C26
 C60
(truncated icosahedron)

C70
The Schlegel diagram of a closed fullerene
is a graph that is planar and 3-regular (or
"cubic"; meaning that all vertices have
degree 3.

A closed fullerene with sphere-like shell

must have at least some cycles that are
pentagons or heptagons. More precisely, if
all the faces have 5 or 6 sides, it follows
from Euler's polyhedron formula, V−E+F=2
(where V, E, F are the numbers of vertices,
edges, and faces), that V must be even,
and that there must be exactly 12
pentagons and V/2−10 hexagons. Similar
constraints exist if the fullerene has
heptagonal (seven-atom) cycles.[47]
Open fullerenes, like carbon nanotubes
and graphene, can consist entirely of
hexagonal rings. In theory, a long nanotube
with ends joined to form a closed torus-
like sheet could also consist entirely of
hexagons.

Bonding

Since each carbon atom is connected to

only three neighbors, instead of the usual
four, it is customary to describe those
bonds as being a mixture of single and
double covalent bonds.

Encapsulation
So-called endohedral fullerenes have ions
or small molecules incorporated inside the
cage atoms.

Research

In the early 2000s, the chemical and

physical properties of fullerenes were a
hot topic in the field of research and
development. Popular Science discussed
possible uses of fullerenes (graphene) in
armor.[48]

In the field of nanotechnology, heat

resistance and superconductivity are
some of the more heavily studied
properties.

There are many calculations that have

been done using ab-initio quantum
methods applied to fullerenes. By DFT and
TD-DFT methods one can obtain IR,
Raman and UV spectra. Results of such
calculations can be compared with
experimental results.

Fullerene is an unusual reactant in many

organic reactions such as the Bingel
reaction discovered in 1993.

Aromaticity
Researchers have been able to increase
the reactivity of fullerenes by attaching
active groups to their surfaces.
Buckminsterfullerene does not exhibit
"superaromaticity": that is, the electrons in
the hexagonal rings do not delocalize over
the whole molecule.

A spherical fullerene of n carbon atoms

has n pi-bonding electrons, free to
delocalize. These should try to delocalize
over the whole molecule. The quantum
mechanics of such an arrangement should
be like one shell only of the well-known
quantum mechanical structure of a single
atom, with a stable filled shell for n = 2, 8,
18, 32, 50, 72, 98, 128, etc.; i.e. twice a
perfect square number; but this series
does not include 60. This 2(N + 1)2 rule
(with N integer) for spherical aromaticity is
the three-dimensional analogue of
Hückel's rule. The 10+ cation would satisfy
this rule, and should be aromatic. This has
been shown to be the case using quantum
chemical modelling, which showed the
existence of strong diamagnetic sphere
currents in the cation.[49]

As a result, C60 in water tends to pick up

two more electrons and become an anion.
The nC60 described below may be the
result of C60 trying to form a loose metallic
bond.

Reactions
Polymerization

Under high pressure and temperature,

buckyballs collapse to form various one-,
two-, or three-dimensional carbon
frameworks. Single-strand polymers are
formed using the Atom Transfer Radical
Addition Polymerization (ATRAP) route[50]

"Ultrahard fullerite" is a coined term

frequently used to describe material
produced by high-pressure high-
temperature (HPHT) processing of
fullerite. Such treatment converts fullerite
into a nanocrystalline form of diamond
which has been reported to exhibit
remarkable mechanical properties.[51]

Fullerite (scanning electron microscope image)

Chemistry

Fullerenes are stable, but not totally

unreactive. The sp2-hybridized carbon
atoms, which are at their energy minimum
in planar graphite, must be bent to form
the closed sphere or tube, which produces
angle strain. The characteristic reaction of
fullerenes is electrophilic addition at 6,6-
double bonds, which reduces angle strain
by changing sp2-hybridized carbons into
sp3-hybridized ones. The change in
hybridized orbitals causes the bond angles
to decrease from about 120° in the sp2
orbitals to about 109.5° in the sp3 orbitals.
This decrease in bond angles allows for
the bonds to bend less when closing the
sphere or tube, and thus, the molecule
becomes more stable.
Other atoms can be trapped inside
fullerenes to form inclusion compounds
known as endohedral fullerenes. An
unusual example is the egg-shaped
fullerene Tb3N@C84, which violates the
isolated pentagon rule.[52] Recent evidence
for a meteor impact at the end of the
Permian period was found by analyzing
noble gases so preserved.[53]
Metallofullerene-based inoculates using
the rhonditic steel process are beginning
production as one of the first
commercially viable uses of buckyballs.

Solubility
C60 in solution

C60 in extra virgin olive oil showing the characteristic

purple color of pristine C60 solutions

Fullerenes are soluble in many organic

solvents, such as toluene, chlorobenzene,
and 1,2,3-trichloropropane. Solubilities are
generally rather low, like 8 g/L for C60 in
carbon disulfide. Still, fullerenes are the
only known allotrope of carbon that can be
dissolved in common solvents at room
temperature. [54][55][56][57][58] Among the
best solvents is 1-chloronaphthalene,
which will dissolve 51 g/L of C60.

Solutions of pure buckminsterfullerene

have a deep purple color. Solutions of C70
are a reddish brown. The higher fullerenes
C76 to C84 have a variety of colors.

Millimeter-sized crystals of C60 and C70,

both pure and solvated, can be grown from
benzene solution. Crystallization of C60
from benzene solution below 30 °C (when
solubility is maximum) yields a triclinic
solid solvate C60·4C6H6. Above 30 °C one
obtains solvate-free fcc C60.[59][60]

Quantum mechanics

In 1999, researchers from the University of

Vienna demonstrated that wave-particle
duality applied to molecules such as
fullerene.[61]

Superconductivity
Fullerenes are normally electrical
insulators, but when crystallized with alkali
metals, the resultant compound can be
conducting or even superconducting.[62]

Chirality

Some fullerenes (e.g. C76, C78, C80, and

C84) are inherently chiral because they are
D2-symmetric, and have been successfully
resolved. Research efforts are ongoing to
develop specific sensors for their
enantiomers.

Stability
Two theories have been proposed to
describe the molecular mechanisms that
make fullerenes. The older, “bottom-up”
theory proposes that they are built atom-
by-atom. The alternative “top-down”
approach claims that fullerenes form when
much larger structures break into
constituent parts.[63]

In 2013 researchers discovered that

asymmetrical fullerenes formed from
larger structures settle into stable
fullerenes. The synthesized substance
was a particular metallofullerene
consisting of 84 carbon atoms with two
additional carbon atoms and two yttrium
atoms inside the cage. The process
produced approximately 100
micrograms.[63]

However, they found that the asymmetrical

molecule could theoretically collapse to
form nearly every known fullerene and
metallofullerene. Minor perturbations
involving the breaking of a few molecular
bonds cause the cage to become highly
symmetrical and stable. This insight
supports the theory that fullerenes can be
formed from graphene when the
appropriate molecular bonds are
severed.[63][64]
Systematic naming
According to the IUPAC, to name a
fullerene, one must cite the number of
member atoms for the rings which
comprise the fullerene, its symmetry point
group in the Schoenflies notation, and the
total number of atoms. For example,
buckminsterfullerene C60 is
systematically named (C60-Ih)
[5,6]fullerene. The name of the point group
should be retained in any derivative of said
fullerene, even if that symmetry is lost by
the derivation.

To indicate the position of substituted or

attached elements, the fullerene atoms are
usually numbered in spiral pathway,
usually starting with the ring on one of the
main axes. If the structure of the fullerene
does not allow such numbering, another
starting atom was chosen to still achieve a
spiral path sequence.

The latter is the case for C70, which is

(C70-D5h(6))[5,6]fullerene in IUPAC notation.
The symmetry D5h(6) means that this is the
isomer where the C5 axis goes through a
pentagon surrounded by hexagons rather
than pentagons.[46]
(C60-Ih)[5,6]fullerene
Carbon numbering.

(C70-D5h(6))[5,6]fullerene
Carbon numbering.

(C70-D5h(6))[5,6]fullerene
Non-equivalent bonds shown by different
colours.
3'H-Cyclopropa[1,2](C70-D5h(6))
[5,6]fullerene.
3'H-Cyclopropa[2,12](C70-D5h(6))
[5,6]fullerene.
 C71-PCBM, [1,2]-isomer.
IUPAC name is methyl 4-(3’-phenyl-3’H-
cyclopropa[1,2](C70-D5h(6))[5,6]fullerene-3’-
yl)butyrate.

In IUPAC's nomenclature, fully saturated

analogues of fullerenes are called
fulleranes. If the mesh has other
element(s) substituted for one or more
carbons, the compound is named a
heterofullerene. If a double bond is
replaced by a methylene bridge –CH2–, the
resulting structure is a homofullerene. If
an atom is fully deleted and missing
valences saturated with hydrogen atoms, it
is a norfullerene. When bonds are removed
(both sigma and pi), the compound
becomes secofullerene; if some new
bonds are added in an unconventional
order, it is a cyclofullerene.[46]

Production
Fullerene production generally starts by
producing fullerene-rich soot. The original
(and still current) method was to send a
large electric current between two nearby
graphite electrodes in an inert
atmosphere. The resulting electric arc
vaporizes the carbon into a plasma that
then cools into sooty residue.[13]
Alternatively, soot is produced by laser
ablation of graphite or pyrolysis of
aromatic hydrocarbons. Combustion is the
most efficient process, developed at
MIT.[65][66]

These processes yield a mixture of various

fullerenes and other forms of carbon. The
fullerenes are then extracted from the soot
using appropriate organic solvents and
separated by chromatography.[67]:p.369 One
can obtain milligram quantities of
fullerenes with 80 atoms or more. C76, C78
and C84 are available commercially.

Applications
Fullerenes have been extensively used for
several biomedical applications including
the design of high-performance MRI
contrast agents, X-ray imaging contrast
agents, photodynamic therapy and drug
and gene delivery, summarized in several
comprehensive reviews.[68]

Medical research
In April 2003, fullerenes were under study
for potential medicinal use: binding
specific antibiotics to the structure to
target resistant bacteria and even target
certain cancer cells such as melanoma.
The October 2005 issue of Chemistry &
Biology contained an article describing the
use of fullerenes as light-activated
antimicrobial agents.[69]

Tumor research

While past cancer research has involved

radiation therapy, photodynamic therapy is
important to study because breakthroughs
in treatments for tumor cells will give more
options to patients with different
conditions. Recent experiments using
HeLa cells in cancer research involves the
development of new photosensitizers with
increased ability to be absorbed by cancer
cells and still trigger cell death. It is also
important that a new photosensitizer does
not stay in the body for a long time to
prevent unwanted cell damage.[70]

Fullerenes can be made to be absorbed by

HeLa cells. The C60 derivatives can be
delivered to the cells by using the
functional groups L-phenylalanine, folic
acid, and L-arginine among others.[71]
Functionalizing the fullerenes aims to
increase the solubility of the molecule by
the cancer cells. Cancer cells take up
these molecules at an increased rate
because of an upregulation of transporters
in the cancer cell, in this case amino acid
transporters will bring in the L-arginine and
L-phenylalanine functional groups of the
fullerenes.[72]

Once absorbed by the cells, the C60

derivatives would react to light radiation by
turning molecular oxygen into reactive
oxygen which triggers apoptosis in the
HeLa cells and other cancer cells that can
absorb the fullerene molecule. This
research shows that a reactive substance
can target cancer cells and then be
triggered by light radiation, minimizing
damage to surrounding tissues while
undergoing treatment.[73]

When absorbed by cancer cells and

exposed to light radiation, the reaction that
creates reactive oxygen damages the DNA,
proteins, and lipids that make up the
cancer cell. This cellular damage forces
the cancerous cell to go through
apoptosis, which can lead to the reduction
in size of a tumor. Once the light radiation
treatment is finished the fullerene will
reabsorb the free radicals to prevent
damage of other tissues.[74] Since this
treatment focuses on cancer cells, it is a
good option for patients whose cancer
cells are within reach of light radiation. As
this research continues, the treatment may
penetrate deeper into the body and be
absorbed by cancer cells more
effectively.[70]

Safety and toxicity

Lalwani et al. published a comprehensive
review on fullerene toxicity in 2013.[68]
These authors review the works on
fullerene toxicity beginning in the early
1990s to present, and conclude that very
little evidence gathered since the
discovery of fullerenes indicate that C60 is
toxic. The toxicity of these carbon
nanoparticles is not only dose- and time-
dependent, but also depends on a number
of other factors such as:

type (e.g.: C60, C70, M@C60, M@C82

functional groups used to water-
solubilize these nanoparticles (e.g.: OH,
COOH)
method of administration (e.g.:
intravenous, intraperitoneal)

The authors therefore recommend

assessing the pharmacology of every new
fullerene- or metallofullerene-based
complex individually as a different
compound.

Popular culture
Examples of fullerenes in popular culture
are numerous. Fullerenes appeared in
fiction well before scientists took serious
interest in them. In a humorously
speculative 1966 column for New
Scientist, David Jones suggested that it
may be possible to create giant hollow
carbon molecules by distorting a plane
hexagonal net by the addition of impurity
atoms.[75]
See also
Buckypaper
Carbocatalysis
Dodecahedrane
Fullerene ligand
Goldberg–Coxeter construction
Lonsdaleite
Truncated rhombic triacontahedron

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External links

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Nanocarbon: From Graphene to

Buckyballs Interactive 3D models of
cyclohexane, benzene, graphene,
graphite, chiral & non-chiral nanotubes,
and C60 Buckyballs -
WeCanFigureThisOut.org.
Properties of C60 fullerene
Richard Smalley's autobiography at
Nobel.se
Sir Harry Kroto's webpage
Simple model of Fullerene
Rhonditic Steel
Introduction to fullerites
Bucky Balls, a short video explaining the
structure of C60 by the Vega Science
Trust
Giant Fullerenes, a short video looking at
Giant Fullerenes
Graphene , 15 September 2010, BBC
Radio program Discovery
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