Solubility of fullerenes

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C
60 in solution C60 Fullerene solution.jpg
C
60
in solution
C
60 in extra virgin olive oil showing the characteristic purple color of pristine C
60 solutions Carbon 60 Olive Oil Solution.JPG
C
60
in extra virgin olive oil showing the characteristic purple color of pristine C
60
solutions

The solubility of fullerenes is generally low. Carbon disulfide dissolves 8g/L of C60, and the best solvent (1-chloronaphthalene) dissolves 53 g/L. up Still, fullerenes are the only known allotrope of carbon that can be dissolved in common solvents at room temperature. Besides those two, good solvents for fullerenes include 1,2-dichlorobenzene, toluene, p-xylene, and 1,2,3-tribromopropane. Fullerenes are highly insoluble in water, and practically insoluble in methanol.

Contents

Solutions of pure C60 (buckminsterfullerene) have a deep purple color. Solutions of C70 are reddish brown. Larger fullerenes C
76
to C
84
have a variety of colors. C
76
has two optical forms, while other larger fullerenes have several structural isomers.

General considerations

Some fullerene structures are not soluble because they have a small band gap between the ground and excited states. These include the small fullerenes C
28
, [1] C
36
and C
50
. The C
72
structure is also in this class, but the endohedral version with a trapped lanthanide-group atom is soluble due to the interaction of the metal atom and the electronic states of the fullerene. Researchers had originally been puzzled by C
72
being absent in fullerene plasma-generated soot extract, but found in endohedral samples. Small band gap fullerenes are highly reactive and bind to other fullerenes or to soot particles.

Solubility of C
60
in some solvents shows unusual behaviour due to existence of solvate phases (analogues of crystallohydrates). For example, solubility of C
60
in benzene solution shows maximum at about 313 K. Crystallization from benzene solution at temperatures below maximum results in formation of triclinic solid solvate with four benzene molecules C
60
·4C
6
H6 which is rather unstable in air. Out of solution, this structure decomposes into usual face-centered cubic (fcc) C
60
in few minutes' time. At temperatures above solubility maximum the solvate is not stable even when immersed in saturated solution and melts with formation of fcc C
60
. Crystallization at temperatures above the solubility maximum results in formation of pure fcc C
60
. Millimeter-sized crystals of C
60
and C
70
can be grown from solution both for solvates and for pure fullerenes. [2] [3]

Solubility table

The following are some solubility values for C
60
and C
70
from the literature, in grams per liter. [4] [5] [6] [7] [8]

SolventC
60
C
70
1-chloronaphthalene 51ND
1-methylnaphthalene 33ND
1,2-dichlorobenzene 2436.2
1,2,4-trimethylbenzene 18ND
tetrahydronaphthalene 16ND
carbon disulfide 89.875
1,2,3-tribromopropane 8ND
chlorobenzene 7ND
p-xylene 53.985
bromoform 5ND
cumene 4ND
toluene 31.406
benzene 1.51.3
carbon tetrachloride 0.4470.121
chloroform 0.25ND
n-hexane 0.0460.013
cyclohexane 0.0350.08
tetrahydrofuran 0.006ND
acetonitrile 0.004ND
methanol 4.0×10−5ND
water 1.3×10−11ND
pentane 0.0040.002
heptane ND0.047
octane 0.0250.042
isooctane 0.026ND
decane 0.0700.053
dodecane 0.0910.098
tetradecane 0.126ND
acetone ND0.0019
isopropanol ND0.0021
dioxane 0.0041ND
mesitylene 0.9971.472
dichloromethane 0.2540.080
ND = not determined

See also

Related Research Articles

<span class="mw-page-title-main">Fullerene</span> Allotrope of carbon

A fullerene is an allotrope of carbon whose molecules consist 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 six atoms. The molecules may have hollow sphere- and ellipsoid-like forms, tubes, or other shapes.

<span class="mw-page-title-main">Toluene</span> Chemical compound

Toluene, also known as toluol, is a substituted aromatic hydrocarbon with the chemical formula C6H5CH3, often abbreviated as PhCH3, where Ph stands for the phenyl group. It is a colorless, water-insoluble liquid with the odor associated with paint thinners. It is a mono-substituted benzene derivative, consisting of a methyl group (CH3) attached to a phenyl group by a single bond. As such, its systematic IUPAC name is methylbenzene. Toluene is predominantly used as an industrial feedstock and a solvent.

<span class="mw-page-title-main">Solvent</span> Substance dissolving a solute resulting in a solution

A solvent is a substance that dissolves a solute, resulting in a solution. A solvent is usually a liquid but can also be a solid, a gas, or a supercritical fluid. Water is a solvent for polar molecules, and the most common solvent used by living things; all the ions and proteins in a cell are dissolved in water within the cell.

<span class="mw-page-title-main">Solvation</span> Association of molecules of a solvent with molecules or ions of a solute

Solvations describes the interaction of a solvent with dissolved molecules. Both ionized and uncharged molecules interact strongly with a solvent, and the strength and nature of this interaction influence many properties of the solute, including solubility, reactivity, and color, as well as influencing the properties of the solvent such as its viscosity and density. If the attractive forces between the solvent and solute particles are greater than the attractive forces holding the solute particles together, the solvent particles pull the solute particles apart and surround them. The surrounded solute particles then move away from the solid solute and out into the solution. Ions are surrounded by a concentric shell of solvent. Solvation is the process of reorganizing solvent and solute molecules into solvation complexes and involves bond formation, hydrogen bonding, and van der Waals forces. Solvation of a solute by water is called hydration.

<span class="mw-page-title-main">Buckminsterfullerene</span> Cage-like allotrope of carbon

Buckminsterfullerene is a type of fullerene with the formula C60. It has a cage-like fused-ring structure (truncated icosahedron) made of twenty hexagons and twelve pentagons, and resembles a soccer ball. Each of its 60 carbon atoms is bonded to its three neighbors.

<span class="mw-page-title-main">Solubility</span> Capacity of a substance to dissolve in a homogeneous way

In chemistry, solubility is the ability of a substance, the solute, to form a solution with another substance, the solvent. Insolubility is the opposite property, the inability of the solute to form such a solution.

<span class="mw-page-title-main">Coronene</span> Chemical compound

Coronene is a polycyclic aromatic hydrocarbon (PAH) comprising seven peri-fused benzene rings. Its chemical formula is C
24
H
12
. It is a yellow material that dissolves in common solvents including benzene, toluene, and dichloromethane. Its solutions emit blue light fluorescence under UV light. It has been used as a solvent probe, similar to pyrene.

<span class="mw-page-title-main">Lithium diisopropylamide</span> Chemical compound

Lithium diisopropylamide is a chemical compound with the molecular formula LiN(CH 2)2. It is used as a strong base and has been widely utilized due to its good solubility in non-polar organic solvents and non-nucleophilic nature. It is a colorless solid, but is usually generated and observed only in solution. It was first prepared by Hamell and Levine in 1950 along with several other hindered lithium diorganylamides to effect the deprotonation of esters at the α position without attack of the carbonyl group.

<span class="mw-page-title-main">Terephthalic acid</span> Chemical compound

Terephthalic acid is an organic compound with formula C6H4(CO2H)2. This white solid is a commodity chemical, used principally as a precursor to the polyester PET, used to make clothing and plastic bottles. Several million tons are produced annually. The common name is derived from the turpentine-producing tree Pistacia terebinthus and phthalic acid.

<span class="mw-page-title-main">Endohedral fullerene</span> Fullerene molecule with additional atoms, ions, or clusters enclosed within itself

Endohedral fullerenes, also called endofullerenes, are fullerenes that have additional atoms, ions, or clusters enclosed within their inner spheres. The first lanthanum C60 complex called La@C60 was synthesized in 1985. The @ (at sign) in the name reflects the notion of a small molecule trapped inside a shell. Two types of endohedral complexes exist: endohedral metallofullerenes and non-metal doped fullerenes.

<span class="mw-page-title-main">18-Crown-6</span> Chemical compound

18-Crown-6 is an organic compound with the formula [C2H4O]6 and the IUPAC name of 1,4,7,10,13,16-hexaoxacyclooctadecane. It is a white, hygroscopic crystalline solid with a low melting point. Like other crown ethers, 18-crown-6 functions as a ligand for some metal cations with a particular affinity for potassium cations (binding constant in methanol: 106 M−1). The point group of 18-crown-6 is S6. The dipole moment of 18-crown-6 is solvent- and temperature-dependent. Below 25 °C, the dipole moment of 18-crown-6 is 2.76 ± 0.06 D in cyclohexane and 2.73 ± 0.02 in benzene. The synthesis of the crown ethers led to the awarding of the Nobel Prize in Chemistry to Charles J. Pedersen.

<span class="mw-page-title-main">Prato reaction</span> Example of the well-known 1,3-dipolar cycloaddition of azomethine ylides to olefins

The Prato reaction is a particular example of the well-known 1,3-dipolar cycloaddition of azomethine ylides to olefins. In fullerene chemistry this reaction refers to the functionalization of fullerenes and nanotubes. The amino acid sarcosine reacts with paraformaldehyde when heated at reflux in toluene to an ylide which reacts with a double bond in a 6,6 ring position in a fullerene via a 1,3-dipolar cycloaddition to yield a N-methylpyrrolidine derivative or pyrrolidinofullerene or pyrrolidino[[3,4:1,2]] [60]fullerene in 82% yield based on C60 conversion.

Endohedral hydrogen fullerene (H2@C60) is an endohedral fullerene containing molecular hydrogen. This chemical compound has a potential application in molecular electronics and was synthesized in 2005 at Kyoto University by the group of Koichi Komatsu. Ordinarily the payload of endohedral fullerenes are inserted at the time of the synthesis of the fullerene itself or is introduced to the fullerene at very low yields at high temperatures and high pressure. This particular fullerene was synthesised in an unusual way in three steps starting from pristine C60 fullerene: cracking open the carbon framework, insert hydrogen gas and zipping up by organic synthesis methods.

<span class="mw-page-title-main">Fullerene chemistry</span>

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.

Recrystallization is a method used to purify chemicals by dissolving a mixture of a compound and its impurities, in an appropriate solvent, prior to heating the solution. Following the dissolution of crude product, the mixture will passively cool, yielding a crystallized compound and its impurities as separate entities. The newly formed crystals can then be subjected to x-ray anaylsis for purity assessment.

C<sub>70</sub> fullerene Chemical compound

C70 fullerene is the fullerene molecule consisting of 70 carbon atoms. It is a cage-like fused-ring structure which resembles a rugby ball, made of 25 hexagons and 12 pentagons, with a carbon atom at the vertices of each polygon and a bond along each polygon edge. A related fullerene molecule, named buckminsterfullerene (or C60 fullerene) consists of 60 carbon atoms.

<span class="mw-page-title-main">Transition metal fullerene complex</span> Chemical compounds containing spheroidical carbon compounds

A transition metal fullerene complex is a coordination complex wherein fullerene serves as a ligand. Fullerenes are typically spheroidal carbon compounds, the most prevalent being buckminsterfullerene, C60.

<span class="mw-page-title-main">Cycloparaphenylene</span>

A cycloparaphenylene is a molecule that consists of several benzene rings connected by covalent bonds in the para positions to form a hoop- or necklace-like structure. Its chemical formula is [C6H4]n or C
6n
H
4n
Such a molecule is usually denoted [n]CPP where n is the number of benzene rings.

<span class="mw-page-title-main">Pentaphenylantimony</span> Chemical compound

Pentaphenylantimony is an organoantimony compound containing five phenyl groups attached to one antimony atom. It has formula Sb(C6H5)5 (or SbPh5).

Magnesium permanganate is an inorganic compound with the chemical formula Mg(MnO4)2. It can be used as an oxidant.

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