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.
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.
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
6H6 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]
The following are some solubility values for C
60 and C
70 from the literature, in grams per liter.
[4]
[5]
[6]
[7]
[8]
Solvent | C 60 |
C 70 |
---|---|---|
1-chloronaphthalene | 51 | ND |
1-methylnaphthalene | 33 | ND |
1,2-dichlorobenzene | 24 | 36.2 |
1,2,4-trimethylbenzene | 18 | ND |
tetrahydronaphthalene | 16 | ND |
carbon disulfide | 8 | 9.875 |
1,2,3-tribromopropane | 8 | ND |
chlorobenzene | 7 | ND |
p- xylene | 5 | 3.985 |
bromoform | 5 | ND |
cumene | 4 | ND |
toluene | 3 | 1.406 |
benzene | 1.5 | 1.3 |
carbon tetrachloride | 0.447 | 0.121 |
chloroform | 0.25 | ND |
n- hexane | 0.046 | 0.013 |
cyclohexane | 0.035 | 0.08 |
tetrahydrofuran | 0.006 | ND |
acetonitrile | 0.004 | ND |
methanol | 4.0×10−5 | ND |
water | 1.3×10−11 | ND |
pentane | 0.004 | 0.002 |
heptane | ND | 0.047 |
octane | 0.025 | 0.042 |
isooctane | 0.026 | ND |
decane | 0.070 | 0.053 |
dodecane | 0.091 | 0.098 |
tetradecane | 0.126 | ND |
acetone | ND | 0.0019 |
isopropanol | ND | 0.0021 |
dioxane | 0.0041 | ND |
mesitylene | 0.997 | 1.472 |
dichloromethane | 0.254 | 0.080 |
ND = not determined |