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Fullerene chemistry is a field of organic chemistry devoted to the chemical properties of fullerenes. 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: exohedral fullerenes with substituents outside the cage and endohedral fullerenes with trapped molecules inside the cage.
1 Chemical properties of fullerenes 2 Fullerene reactions 2.1 Nucleophilic addition 2.2 Pericyclic reactions 2.3 Hydrogenation 2.4 Oxidation 2.5 Hydroxylation 2.6 Electrophilic addition 2.7 Retro additions 2.8 Carbene additions 2.9 Radical additions 3 Fullerenes as ligands 4 Multistep fullerene synthesis 4.1 Multistep nanoribbon synthesis 5 Open-cage fullerenes 6 Heterofullerenes 7 Fullerene dimers 8 Nanotube chemistry 9 Fullerene purification 9.1 Experimental purification strategies 10 References
Chemical properties of fullerenes
See also: Endohedral fullerenes Fullerene or C60 is soccer-ball-shaped or Ih with 12 pentagons and 20 hexagons. According to Euler's theorem these 12 pentagons are required for closure of the carbon network consisting of n hexagons and C 60 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 60 and its relative C 70 obey this so-called isolated pentagon rule (IPR). The next homologue C84 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 Tb3N@C84 with two fused pentagons at the apex of an egg-shaped cage. or as fullerenes with exohedral stabilization such as C 50 Cl10  and reportedly C 60 H8 . Because of the molecule's spherical shape the carbon atoms are highly pyramidalized, which has far-reaching consequences for reactivity. It is estimated that strain energy constitutes 80% of the heat of formation. The conjugated carbon atoms respond to deviation from planarity by orbital rehybridization of the sp² orbitals and pi orbitals to a sp2.27 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 electronegative. The other reason is that the empty low-lying pi* orbitals also have a high s character. The double bonds in fullerene are not all the same. Two groups can be identified: 30 so-called [6,6] double bonds connect two hexagons and 60 [5,6] bonds connect a hexagon and a pentagon. Of the two the [6,6] bonds are shorter with more double-bond character and therefore a hexagon is often represented as a cyclohexatriene and a pentagon as a pentalene or radialene. In other words, although the carbon atoms in fullerene are all conjugated the superstructure is not a super aromatic compound. The X-ray diffraction bond length values are 135.5 pm for the [6,6] bond and 146.7 pm for the [5,6] bond.
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Wikipedia. Pericyclic reactions The [6. Another nucleophilic reaction is the Bingel reaction. 6− 12− Fullerene reactions See also: Bingel reaction and Prato reaction Fullerenes tend to react as electrophiles. Hydrogenation Fullerenes are easily hydrogenated by several methods. and fulleroid to ring-open (methanoannulene) structures. the free encyclopedia Page 2 C60 fullerene has 60 pi electrons but a closed shell configuration requires 72 electrons. Another method is reaction in diluted sodium hydroxide catalysed by TBAH adding 24 to 26 hydroxyl groups.wikipedia. the terms methanofullerene are used to indicate the ring-closed (cyclopropane) fullerene derivatives. Hydroxylation Fullerenes can be hydroxylated to fullerenols or fullerols . completely hydrogenated C60 H60 is only hypothetical because of large strain. The maximum number of hydroxyl groups that can be attached (hydrogen peroxide method) stands at 36–40. In this hydroarylation the reaction product is the 1. Key in this type of reaction is the level of functionalization i. An example of a 1. However. An additional driving force is relief of strain when double bonds become saturated. Examples of nucleophiles are Grignard reagents and organolithium reagents. Examples are the retro-Bingel reaction and the retro-Prato reaction. Fullerene reacts with chlorobenzene and aluminium chloride in a Friedel-Crafts alkylation type reaction. For example the reaction of C 60 with methylmagnesium chloride stops quantitatively at the penta-adduct with the methyl groups centered around a cyclopentadienyl anion which is subsequently protonated. At the final reaction stage this causes collapse of cage structure with formation of polycyclic aromatic hydrocarbons. as prolonged hydrogenation of fullerenes by direct reaction with hydrogen gas at high temperature conditions results in cage fragmentation. Nucleophilic addition Fullerenes react as electrophiles with a host of nucleophiles in nucleophilic additions. Retro additions Protocols have been investigated for removing substituents via retroadditions after they have served their purpose. In conformity with IUPAC rules. The intermediary formed carbanion is captured by another electrophile. Hydroxylation has also been reported using solvent-free NaOH / hydrogen peroxide. Water solubility depends on the total number of hydroxyl groups that can be attached. According to in silico predictions the as yet elusive C60 F60 may have some of the fluorine atoms in endo positions (pointing inwards) and may resemble a tube more than it does a sphere.  Oxidation Although more difficult than reduction. One method is fullerene reaction in diluted sulfuric acid and potassium nitrate to C 60 (OH)15 .Fullerene chemistry .6] bonds of fullerenes react as dienes or dienophiles in cycloadditions for instance Diels-Alder reactions. monoaddition or multiple additions and in case of multiple additions their topological relationships (new substituents huddled together or evenly spaced).e. Examples of hydrofullerenes are C60 H18 and C 60 H36 .3-dipolar cycloaddition to a 5-membered ring is the Prato reaction. Electrophilic addition Fullerenes react in electrophilic additions as well. C60 (OH)8 was prepared using a multistep procedure starting from a mixed peroxide fullerene. The record holder for fluorine addition is C 60 F48 . Highly hydrogenated fullerenes are not stable. http://en. 4-membered rings can be obtained by [2+2]cycloadditions for instance with benzyne. oxidation of fullerene is possible for instance with oxygen and osmium tetraoxide. The fullerene is able to acquire the missing electrons by reaction with potassium to form first the K6 C60 salt and then the K12C60 In this compound the bond length alternation observed in the parent molecule has vanished. The reaction with bromine can add up to 24 bromine atoms to the sphere.2-addition adduct (Ar-CC-H).org/wiki/Fullerene_chemistry 11/5/2013 1:07:28 AM .
6] double bond is electron-deficient and usually forms metallic bonds with η = 2 hapticity. A single addition takes place along a [6. the free encyclopedia Page 3 Carbene additions Fullerenes react with carbenes to methanofullerenes. the organic synthesis of fullerenes remains a challenge for chemistry. The first such open-cage fullerene was reported in 1995.Fullerene chemistry . Bonding modes such as η = 5 or η = 6 can be induced by modification of the coordination sphere. The yield through a combustion method is often above 1%. The reaction of fullerene with dichlorocarbene (created by sodium trichloroacetate pyrolysis) was first reported in 1993. Multistep fullerene synthesis Although the procedure for the synthesis of the C 60 fullerene is well established (generation of a large current between two nearby graphite electrodes in an inert atmosphere) a 2002 study described an organic synthesis of the compound starting from simple organic compounds. In this way it is possible to insert into it small molecules such as hydrogen.org/wiki/Fullerene_chemistry 11/5/2013 1:07:28 AM . The [6. In the final step a large polycyclic aromatic hydrocarbon consisting of 13 hexagons and three pentagons is submitted to flash vacuum pyrolysis at 1100°C and 0. The unpaired electron does not delocalize over the entire sphere but takes up positions in the vicinity of the tBu substituent.Wikipedia. and therefore. The chemical yield is low: 0. in candle burning. http://en.6] bond.wikipedia. A small percentage of fullerenes is formed in any process which involves burning of hydrocarbons. helium or lithium. Radical additions Fullerenes can be considered radical scavengers. With a simple hydrocarbon radical such as the t-butyl radical obtained by thermolysis or photolysis from a suitable precursor the tBuC60 radical is formed that can be studied. In endohedral hydrogen fullerenes the opening. e.1 to 1%. hydrogen insertion and closing back up has already been demonstrated. The three carbon chlorine bonds serve as free radical incubators and the ball is stitched up in a no-doubt complex series of radical reactions. 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 Stone Wales defects could be ruled out. The method proposed above does not provide any advantage for synthesis of fullerenes compared to the usual combustion method. Multistep nanoribbon synthesis In the field of graphene nanoribbons a bottom-up approach has also been investigated  Open-cage fullerenes A part of fullerene research is devoted to so-called open-cage fullerenes  whereby one or more bonds are removed chemically exposing an orifice.g. Fullerenes as ligands Main article: Fullerene ligands Fullerene is a ligand in organometallic chemistry.01 Torr. C60 fullerene reacts with tungsten hexacarbonyl W(CO)6 to the (η²-C 60 )W(CO)5 complex in a hexane solution in direct sunlight.
 The trimer has also been reported using 4-aminopyridine as catalyst (4% yield)  and observed with scanning tunneling microscopy as a monolayer. One example is a DA reaction assisted by chromium hexacarbonyl and high pressure.wikipedia. carboxyl) on the nanotube surface which electrostatically stabilize them in water and which can later be utilized in chemical functionalization. copper. the free encyclopedia Page 4 Heterofullerenes In heterofullerenes at least one carbon atom is replaced by another element. Nanotube chemistry Main article: Selective chemistry of single-walled nanotubes Carbon nanotubes.org/wiki/Fullerene_chemistry 11/5/2013 1:07:28 AM . silicon. One way to do this is by chemical surface modification. Other tools are UV spectroscopy where pristine nanotubes show distinct Van Hove singularities where functionalized tubes do not. germanium.Fullerene chemistry . carbonyl. and simple TGA analysis. One report  reveals that the oxygen containing http://en. The first available purification method for C60 fullerene was by HPLC from which small amounts could be generated at large expense. Nanotubes can also be alkylated with alkyl halides using lithium or sodium metal and liquid ammonia (Birch reduction conditions).6. A practical laboratory-scale method for purification of soot enriched in C 60 and C 70 starts with extraction in toluene followed by filtration with a paper filter. aniline is oxidized to a diazonium intermediate. Unlike the spherical fullerenes made up of hexagons and pentagons. After expulsion of nitrogen. The initial nanotube salt can function as an polymerization initiator  and can react with peroxides to form alkoxy functionalized nanotubes  Fullerene purification Fullerene purification is the process of obtaining a fullerene compound free of contamination. rhodium  and iridium. oxygen. nickel. A useful tool for the analysis of derivatised nanotubes is Raman spectroscopy which shows a G-band (G for graphite) for the native nanotubes at 1580 cm− 1 and a D-band (D for defect) at 1350 cm− 1 when the graphite lattice is disrupted with conversion of sp² to sp³ hybridized carbon. nanotubes only have hexagons present but in terms of reactivity both systems have much in common. C 70 and higher homologues are always formed.Wikipedia. The solvent is evaporated and the residue (the toluene-soluble soot fraction) redissolved in toluene and subjected to column chromatography. C60 elutes first with a purple color and C70 is next displaying a reddish-brown color. can be described as graphene sheets rolled into a cylindrical tube. Fullerene purification is key to fullerene science and determines fullerene prices and the success of practical applications of fullerenes. It is assumed that this oxidation creates oxygen containing groups (hydroxyl. The ratio of both peaks ID /IG is taken as a measure of functionalization. In fullerene production mixtures of C60 . Reports on isolated heterofullerenes are limited to those based on nitrogen  and oxygen. phosphorus. Based on spectroscopy. Due to electrostatic forces nanotubes have a nasty tendency to cluster together into bundles and many potential applications require an exfoliation process. arsenic. also part of the fullerene family. In nanotube processing the established purification method for removing amorphous carbon and metals is by competitive oxidation (often a sulfuric acid / nitric acid mixture). Fullerene dimers The C60 fullerene dimerizes in a formal [2+2] cycloaddition to a C 120 bucky dumbbell in the solid state by mechanochemistry (high-speed vibration milling) with potassium cyanide as a catalyst. iron. it forms a covalent bond as an aryl radical: Also known are protocols for cycloadditions such as Diels-Alder reactions. In one type of chemical modification. 1. nitrogen (azafullerenes). The ID /IG ratio for reaction with Danishefsky’s diene is 2. substitutions have been reported with boron (borafullerenes).3-dipolar cycloadditions of azomethine ylides and azide–alkyne cycloaddition reactions.
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