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
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]

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

References

  1. ↑ Guo, T.; Smalley, R.E.; Scuseria, G.E. (1993). "Ab initio theoretical predictions of C
    28    , C
    28    H4, C
    28    F4, (Ti@C
    28    )H4, and M@C
    28     (M = Mg, Al, Si, S, Ca, Sc, Ti, Ge, Zr, and Sn)". Journal of Chemical Physics . 99 (1): 352. Bibcode:1993JChPh..99..352G. doi:10.1063/1.465758.
  2. ↑ Talyzin, A.V. (1997). "Phase Transition C
    60    −C
    60    *4C
    6    H6 in Liquid Benzene". Journal of Physical Chemistry B . 101 (47): 9679–9681. doi:10.1021/jp9720303.
  3. ↑ Talyzin, A.V.; Engström, I. (1998). "C
    70     in Benzene, Hexane, and Toluene Solutions". Journal of Physical Chemistry B . 102 (34): 6477–6481. doi:10.1021/jp9815255.
  4. ↑ Beck, Mihály T.; Mándi, Géza (1997). "Solubility of C
    60    ". Fullerenes, Nanotubes and Carbon Nanostructures. 5 (2): 291–310. doi:10.1080/15363839708011993.
  5. ↑ Bezmel'nitsyn, V.N.; Eletskii, A.V.; Okun', M.V. (1998). "Fullerenes in solutions". Physics-Uspekhi . 41 (11): 1091–1114. Bibcode:1998PhyU...41.1091B. doi:10.1070/PU1998v041n11ABEH000502.
  6. ↑ Ruoff, R.S.; Tse, Doris S.; Malhotra, Ripudaman; Lorents, Donald C. (1993). "Solubility of fullerene (C
    60    ) in a variety of solvents"     (PDF). Journal of Physical Chemistry . 97 (13): 3379–3383. doi:10.1021/j100115a049.
  7. ↑ 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.
  8. ↑ 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.
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