The discovery of buckminsterfullerene (C60) in 1985 was an unexpected finding that generated significant interest. In experiments at Rice University in 1985, laser vaporization of graphite produced a strong peak for a carbon cluster with 60 atoms. The researchers concluded this extremely stable cluster was likely a hollow, spherical molecule. Inspired by geodesic dome designs of Buckminster Fuller, they proposed the cluster had the structure of a soccer ball formed from 20 hexagons and 12 pentagons. This buckminsterfullerene molecule, nicknamed "buckyball," launched interest in a new class of carbon structures called fullerenes. In 1990, a method was developed to produce buckyballs in gram quantities, enabling extensive study and applications
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6. BUCKYBALLS
The discovery of a new form of a pure
element is a rather rare occurrence, especially for
a common element. Therefore, reports of such
discoveries generate an unusual amount of
excitement among scientists. An example is the
1985 discovery of a new allotropic form of
elemental carbon. The two well-known forms of
elemental carbon are graphite and diamond. Both
of these contain extended arrays of carbon atoms.
In the new form, the carbon atoms are arranged in
relatively small clusters of atoms.
7. Harold
Kroto
Richard
Smalley
Discovery
Theoretical predictions of buckyball molecules
appeared in the late 1960s – early 1970s,but they
went largely unnoticed. In the early 1970s, the
chemistry of unsaturated carbon configurations
was studied by a group at the University of Sussex,
led by Harry Kroto and David Walton. In the 1980s
a technique was developed by Richard Smalley and
Bob Curl at Rice University, Texas to isolate these
substances. They used laser vaporization of a
suitable target to produce clusters of atoms. Kroto
realized that by using a graphite target any carbon
chains formed could be studied.
8. IUPAC name[hide]
(C60-Ih)[5,6]fullerene
Other names[hide]
Buckyball; Fullerene-C60; [60]fullerene
Identifiers
CAS number 99685-96-8
PubChem 123591
ChemSpider 110185
ChEBI CHEBI:33128
Beilstein Reference 5901022
Jmol-3D images Image 1
SMILES
[show]
InChI
[show]
Properties
Molecular formula C60
Molar mass 720.64 g mol
−1
Appearance Dark needle-like crystals
Density 1.65 g/cm
3
Melting point sublimates at ~600 °C
[1]
Solubility in water insoluble in water
Structure
Crystal structure Face-centered cubic,cF1924
Space group Fm3m, No. 225
Lattice constant a = 0.14154 nm
9.
10.
11. Diamond Graphite C60
Crystal Structure cubic hex. fcc
density (g cm-3) 3.30 2.27 1.65
Lattice constant (A) 3.513 a=2.456 14.15
- b=6.696 -
C-C length (A) 1.54 1.42 1.455
C=C length - - 1.391
Standard heats of
formation (k cal mol-1)
0.4 0.0 9.08
bulk modulus (G Pa) 1200 207 18(174)
melting point (K) 3700 3800 sublm. 800
index of refraction 2.42 - 2.2 (600nm)
conductivity insulator conductor semi conductor
resistivity (ohm m) 1 x 10E18 1.37 x 10E-5 1 x 10E14 (room temp)
naturally occuring
deposit
kimberlite pegmatite shungite
SOME PROPERTIES OF CARBON
12. C - C length (gas phase) 1.458 Å
C = C 1.410 Å
Cage Diameter 7.11 Å
C60 - C60 nearest approach 3.1 Å
Ionisation Potentials
C60 to C60+ 7.6 ± 0.2 eV
C60+ to C60 2+ 12.25 ± 0.5 eV
C602+ to C60 3+ 17.0 ± 0.7 eV
C60 3+ to C60 4+ 21.7 eV by extrapolation
Electron affinity 2.6 eV
Band Gap 1.8 eV
relative permitivity 4.4 ± 0.2
absorption coefficients 6.07 x 10E5 cm-1 @ 220 nm
(thin film) 1.21 x 10E5 cm-1 @ 442 nm
Further properties of Buckminsterfullerene
14. The serendipitous discovery of a third allotropic form in
1985, uncovered a fundamentally different structure of
closed carbon cages, which were to become known
as fullerenes. This new family of non-planar carbon
compounds has generated immense interest within the
scientific community in such a short period of time, with
thousands of papers published about fullerenes and
fullerene-based materials to date.In the early 1970's, the
chemistry of unsaturated carbon configurations was
studied by a group at the University of Sussex, led
by Harry Kroto and David Walton. They developed
methods for synthesising long chain polyynes, whose
vibration-rotation dynamics were studied by microwave
spectroscopy. They then used these observations for
molecular radioastronomy. From 1975-78 they studied the
long-
chained polyynylcyanides, HC5N, HC7N and HC9N.
These molecules were detected in the cloud material of
the interstellar medium by radioastronomy. These
molecules turned out to be produced by red giant stars.
15. In the 1980's a technique was developed by Richard Smalley and Bob Curl at Rice
University, Texas. They used laser vaporisation of a suitable target to produce
clusters of atoms. Kroto realised that by using a graphite target, that the cluster
apparatus would be ideal to probe the formation of carbon chains, and so
planned a collaboration between his group at Sussex and the one at Rice.
The Sussex/Rice experiment took place in September 1985. The technique probed
the carbon plasma produced by the laser vaporisation by time-of-flight mass
spectrometry. The experiments confirmed that large carbon chain/clusters were
being formed. During the experiments it was noted that the peak for the
C60 molecule (and to a lesser extent C70) behaved unusually and formed under all
conditions as well as exhibiting great stability.
The experimental evidence, a strong peak at 720 amu (atomic mass units),
indicated that a carbon molecule with sixty carbon atoms was forming, but
provided little structural information. The research group concluded after
reactivity experiments, that the most likely structure was a spheroidal molecule.
Kroto mentioned Fuller's geodesic dome structures, which
contained pentagons as well as hexagons. The idea was quickly rationalised as
the basis of an icosohedral symmetry closed cage structure. The geodesic and
electronic bonding factors in the structure accounted for the stability of the
molecule, and it was named after Buckminster Fuller.
16. In graphite, the carbon atoms are arranged in sheets with the bonds between the atoms
forming hexagons, something like chicken wire. The sheets are only weakly bonded to
each other, so they slide past one another, giving graphite a slippery feel and making it a
good lubricant. Graphite is also used extensively in studies of the surface effects of energy
in the form of light, heat, and electric current. When graphite is subjected to large bursts
of energy of these sorts, portions of the top sheet of carbon atoms are ripped out. The
ejected portions are studied to learn how the energy interacts with a solid surface.
In the early 1980s, Harold W. Kroto of the University of Sussex in England was
using microwave spectroscopy to analyze the composition of carbon-rich stars. The
analysis indicated that the atmosphere of these stars contained cyanopolyynes, which are
composed of chains of alternating carbon and nitrogen atoms. Prof. Kroto wanted to
study how these chains could be formed. He contacted Robert F. Curl and Richard E.
Smalley at Rice University in Texas because they had been using microwave spectroscopy
to analyze clusters of metals formed in Prof. Smalley’s lab. Prof. Smalley had an
apparatus that could vaporize nearly any material into a plasma. In 1985, Kroto joined
Curl and Smalley in Smalley’s lab to study the products of carbon vaporization. They
fired a high-energy laser beam at a graphite surface and used a stream of helium gas to
carry the fragments into a mass spectrometer. The mass spectrometer revealed the
masses of the fragments of graphite ejected from the surface. These fragments varied
from several atoms up to about 190 atoms. The distribution of fragments depended on
the pressure of helium in the carrier stream. As the pressure increased from several torr
to about 1 atm, the distribution of fragments changed, and the fragment containing sixty
carbon atoms became by far the dominant one. Because the laser pulse and graphite
surface had not changed, they reasoned that the fragments that broke off were not
changing, but instead that the way these fragments interacted on their way into the mass
spectrometer changed. At higher helium pressures, the fragments would be jostled
together more than at lower pressures. This jostling leads to the formation of the most
stable form of small carbon atom cluster, namely C60.
17. What is Buckminsterfullerene?
In 1985 a new allotrope of carbon (C60) was discovered.
Sixty carbon atoms form the shape of a ball like a football
with a carbon atom at each corner
of the 20 hexagons and 12 pentagons.
Each carbon atom (shown below as a circle) has three bonds.
The size of the molecule is almost exactly 1nm in diameter.
The ratio of the size of an ordinary soccer ball
to the planet Earth is the same as
the ratio of the size of a C60 molecule to a soccer ball.
These are not called giant molecules
because there are only sixty atoms.
A large number of these molecules can fit together
to form a transparent yellow solid called fullerite.
18. This form of carbon
was named after the American architect Buckminster Fuller,
who was famous for designing a large geodesic dome
which looked similar (sort of) to the molecular structure of C60.
Many other balls of carbon called fullerenes,
have since been made, including C70, C76, and C84.
These molecules have become known as "buckyballs".
Fullerenes are used as catalysts and lubricants.
They are also used in nanotubes for strengthening materials
(for eaxample sports equipment) and are
sometimes used as a way of delivering drugs into the body
19. Kroto, Smalley, and Curl wondered how
the atoms in this cluster were arranged to
make it more stable than other clusters.
They believed that its stability came from an
arrangement in which all bonding capacity
of the atoms is satisfied. In a small fragment
of carbon-atom sheet ejected from a
graphite surface, the atoms around the edge
of the sheet would not be fully bonded. If,
however, the sheet were to form into a ball
so the edges would meet, the bonding
capacity of all atoms would be satisfied. In
thinking of how the atoms are arranged in
this ball, the scientists considered the
geodesic domes designed by the architect-
engineer, R. Buckminster Fuller. These
domes led them to suspect a structure of
interlocking hexagons and pentagons,
identical to those of a soccer ball. Because
this idea was inspired by the geodesic dome,
they named this C60 allotrope of carbon
buckminsterfullerene.
20. The amounts of buckminsterfullerene (“buckyballs,” for short) prepared by laser
were extremely small. The evidence for the structure would remain sketchy until
C60 could be prepared in larger quantities. Such a preparation was discovered in
1990. In this method, a water-cooled cylinder contains a sharp graphite rod touching
a graphite disk. The cylinder is evacuated to a pressure of 1 × 10-5 torr, and a current
of 100 to 200 ampere is passed between the rod and the disk. This produces a soot
that deposits on the walls of the cylinder. The soot is washed with toluene,
producing a red-brown solution. When this solution is evaporated, it leaves a
residue with a mass of about 10% of the original soot and containing more than 85%
C60. With this method, about 1 gram of C60 can be produced in a day.
A whole new chemistry has developed in which fullerene molecules are
manipulated to form compounds. Because the C60 sphere is hollow, other atoms can
be trapped within it. When a graphite sheet soaked in LaCl3 solution is subjected to
vaporization-condensation experiments, a substance with formula LaC60 is formed.
When other metal salts are used, the ball of carbon atoms can be shrunken with
laser pulses to fit the metal ion within. In this way, CsC48 and KC44 were formed.
Other experiments have produced new materials with C60. For example, C60 doped
with potassium is a superconductor below 18 Kelvin. In the C60 structure, other
atoms have been substituted for the carbon atoms, producing derivatives such as
C59N and C57B3. C60 has also been used to produce three-dimensional polymers.
In addition, tubes of carbon atoms called nanotubes have also been made. In 1996,
Harold Kroto, Richard Smalley, and Robert Curl shared the Nobel Prize in
Chemistry for their discovery of buckminsterfullerene.
21. Beam-experiments conducted between 1985-90 provided
more evidence for the stability of C60 as well as supporting the
closed cage structural theory and predicting some of the bulk
properties such a molecule would have. Around this time,
intense theoretical group theory activity also predicted that
C60 should have only four IR active vibrational bands, on
account of its icosohedral symmetry.In 1989, the
Heidelberg/Tuscon group, led by physicists Wolfgang
Krätschmer and Donald Huffman had observed unusual IR
and UV features in thin carbon films produced by arc-
processed graphite rods. Among other features, the IR spectra
showed four discrete bands in close agreement to those
proposed for C60. A paper published by the group in 1990
followed on from their thin film experiments, and detailed the
extraction of a benzene soluble material from the arc-
processed graphite. This extract was found to crystallise and
X-ray analysis consistent with arrays of spherical
C60 molecules, approximately 7Å in diameter. The
C60 molecule has two bond lengths - the 6:6 ring bonds can be
considered "double bonds" and are shorter than the 6:5 bonds
- see below - the "shorter bonds" are highlighted for clarity:
22. In 1990, W. Krätchmer and D. R. Huffman's
developed a simple and efficient method of
producing fullerenes in gram and even
kilogram amounts which boosted the
fullerene research. In this technique, carbon
soot is produced from two high-purity
graphite electrodes by igniting an arc
discharge between them in an inert
atmosphere (helium gas). Alternatively, soot
is produced by laser ablation of graphite
or pyrolysis of aromatic hydrocarbons.
Fullerenes are extracted from the soot using
a multistep procedure. First, the soot is
dissolved in appropriate organic solvents.
This step yields a solution containing up to
75% of C60, as well as other fullerenes. These
fractions are separated
using chromatography.[12]
23. References
^ Eiji Ōsawa (2002). Perspectives of fullerene nanotechnology. Springer. pp. 275–
. ISBN 978-0-7923-7174-8. Retrieved 26 December 2011.
^ Kroto, H. W.; Heath, J. R.; O'Brien, S. C.; Curl, R. F.; Smalley, R. E. (1985). "C60:
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29.
It's stronger than it looks.
It superconducts (conducts electricity really well) when you fiddle with it enough.
It insulates (doesn't conduct at all) on that same token.
It conducts like an ordinary metal.
It even semiconducts (a bit like silicon) under the right conditions.
You can make it switch between all these states by playing with it.
Some pharmaceutical companies are developing products containing C60 to make you look younger. However, C60 has not been
tested properly for toxicity yet.
Some people have made transistors out of it.
It's hollow, so you can wrap it around single atoms and trap them 'in a cage'.
Somebody went and made an amplifier using a single molecule of it.
It's optically active, meaning that if you put it in front of a light source, you can use it to switch the light on and off, and things
like that. It can be really useful if you are a telecommunications engineer.
Bioactivity is another application, C60 can be made to fiddle with DNA and some sugars.
Because the molecule is a tiny strong sphere, it can be used as a microscopic ball bearing for very small machines.
There are more applications and a great many academic papers have been published concerning C60, but the list could become
long and boring and it's growing daily. It could also be the first step into nanotechnology.
So there you have it: a molecule so new and weird, they don't even know what to do with it yet.
37. solid* Gas phase Ar matrix
(cm-1) 1429.0 1406.9 1431.9
1182.5 1169.1 1184.8
576.5 570.3 579.3
527.0 527.0 530.0
(micro m) 6.998 7.108 6.984
8.456 8.554 8.440
17.35 17.53 17.26
18.87 18.98 18.87
SPECTROSCOPIC DATA
Rotational constant
0.0028 cm-1
IR active bands - four T1u
38. nm cm-1 log emax eV
211.0 47393 5.20 5.88
227.4 43975 4.95 5.46
256.6 38971 5.24 4.83
328.4 30451 4.72 3.78
377.0 26525 3.79 3.29
404.0 24754 3.47 3.07
UV and visible bands (hexane)
a broad weak band also exists between 440 - 670 nm.
Also detected are bands assigned to the ions;
C60+ at 973 nm and C60- at 1068 nm.
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55. Join my process development group on google
http://groups.google.com/group/organic-
process-development
56.
57. DR ANTHONY MELVIN CRASTO Ph.D
amcrasto@gmail.com
MBILE-+91 9323115463
GLENMARK SCIENTIST , NAVIMUMBAI,
INDIA
web link
http://anthonycrasto.jimdo.com/
http://www.anthonymelvincrasto.yolasite.com/
http://www.slidestaxx.com/anthony-melvin-crasto-phd
https://sites.google.com/site/anthonycrastoorganicchemistry/sites---
my-own-on-the-net
http://anthonycrasto.wordpress.com/
http://organicchemistrysite.blogspot.com/
http://www.mendeley.com/profiles/anthony-melvin-crasto/
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