Solubility of fullerenesC 60 in solutionC 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.
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 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]
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]
↑Sivaraman, N.; Dhamodaran, R.; Kaliappan, I.; Srinivasan, T. G.; Vasudeva Rao, P. R. P.; Mathews, C. K. C. (1994). "Solubility of C 70 in Organic Solvents". Fullerene Science and Technology. 2 (3): 233–246. doi:10.1080/15363839408009549.
↑Semenov, K. N.; Charykov, N. A.; Keskinov, V. A.; Piartman, A. K.; Blokhin, A. A.; Kopyrin, A. A. (2010). "Solubility of Light Fullerenes in Organic Solvents". Journal of Chemical & Engineering Data. 55: 13–36. doi:10.1021/je900296s.