324
KUIMOV et al.
2. Troshin, P.A., Troshina, O.A., Lyubovskaya, R.N., and
Razumov, V.F., Funktsional’nye proizvodnye fullerenov:
metody sinteza i perspektivy ispol’zovaniya v organich-
eskoi elektronike i biomeditsine (Functional Fullerene
Derivatives: Methods of synthesis, and Prospects for
Use in Organic Electronics and Biomedicine), Iva-
novo: Izd. IvGU, 2010.
the majority of xylene was decanted from the precipi-
tate, the latter was centrifuged, washed with ether (2 ×
5 mL), and dried in a vacuum. Finally, 20 mg of oli-
gofullerene 1b was obtained (yield 18% toward reacted
C60) as a brown powder slightly soluble in hot DMSO
and CS2 and insoluble in CHCl3, THF, and water.
Unreacted C60 (24 mg, conversion 76%) was recovered
from xylene.
3. Tzirakis, M.D. and Orfanopoulos, M., Chem. Rev.,
2013, vol. 113, pp. 5262–5321.
4. Medicinal Chemistry and Pharmacological Potential of
Fullerenes and Carbon Nanotubes, Cataldo, F. and Da
Ros, T., Eds., Berlin: Springer, 2008, vol. 1, p. 408.
Melting point > 300°C (dec). Elemental analysis.
Found (%): C, 68.86; H, 2.02; P, 11.95.
EDX. Found (%): C, 68.40; P, 12.01.
5. Wilson, L.J., Interface, 1999, vol. 8, pp. 24–28.
For [H3C60]2(PO2H2)3(PO3H2)5 ⋅ 3H2O anal.
6. Cheng, F.Y., Yang, X.L., Fan, C.H., and Zhu, H.S.,
Tetrahedron, 2001, vol. 57, no. 34, pp. 7331–7335.
calcd. (%): C, 68.59; H, 1.34; P, 11.79.
1H NMR (DMSO-d6, δ, ppm, J, Hz): 7.04 (s,
7. Gonzalez, K.A., Wilson, L.J., Wu, W.J., and Nancol-
las, G.H., Bioorg. Med. Chem., 2002, vol. 10, no. 6, pp.
1991–1997.
C60H), 7.07 (s, C60H), 7.10 (s, C60H), 6.69 (d, JPH
=
635, 3H, PH), 3.67 (s, 1H, OH).
8. Mirakyan, A.L. and Wilson, L.J., J. Chem. Soc., Perkin
31P NMR (DMSO-d6, δ, ppm, J, Hz): 2.09 and
–0.13 (∼1 : 1.5).
Trans., 2002, no. 6, pp. 1173–1176.
9. Lu, Y., Cheng, H., Xin, X., and Xin, T., and
XinLin, T.X., Sci. China Ser. B: Chem., 2009, vol. 52,
no. 5, pp. 626–631.
IR (KBr, ν, cm–1): 526 (ν C60), 942 (sh, δ P–OH),
s
as
1001 (δ OH, ν PO2 ), 1160 (ν PO2 , ν P=O), 1182
10. Cheng, F.Y., Yang, X.L., Zhu, H.S., and Song, Y.L.,
(ν C60), 1208, 1402, 1428 (ν C60), 1459, 1513 (δ CH),
Tetrahedron Lett., 2000, vol. 41, no. 20, pp. 3947–3950.
1630 (ν C=C, ν OHC), 2327 (ν PH), 2422 (ν OHB),
2680 (ν OHA), 2851, 2918, 2976 (ν CH), 3264, 3433
(ν OH, P–OH).
11. Troshin, P.A., Romanova, I.P., Susarova, D.K.,
Yusupova, G.G., Gubaidullin, A.T., Saifina, A.F.,
Zverev, V.V., Lyubovskaya, R.N., Razumov, V.F., and
Sinyashin, O.G., Mendeleev Commun., 2010, vol. 20,
no. 3, pp. P. 137–139.
ACKNOWLEDGMENTS
12. Kyoji, K.Jap., Jpn Patent 2010, JP 2010037277 A,
Chem. Abstr., 2010, vol. 152, no. 267729.
Equipment of Baikal Analytical Shared Facility
Center, Siberian Branch, Russian Academy of Sci-
ences, was used in the work.
This work was supported by the Council for Grants of
the President of the Russian Federation for Support of
Leading Scientific Schools (grant no. NSh 7145.2016.3).
13. Yurkova, A.A., Khakina, E.A., Troyanov, S.I.,
Chernyak, A., Shmygleva, L., Peregudov, A.S., Mar-
tynenko, V.M., Dobrovolskiy, Y.A., and Troshin, P.A.,
Chem. Commun., 2012, vol. 48, no. 71, pp. 8916–8918.
14. Gusarova, N.K., Malysheva, S.F., Kuimov, V.A., Belo-
gorlova, N.A., Mikhailenko, V.L., and Trofimov, B.A.,
Mendeleev Commun., 2008, vol. 18, no. 5, pp. 260–261.
15. Niklas, J., Mardis, K.L., Banks, B.P., Grooms, G.M.,
Sperlich, A., Dyakonov, V., Beaupre, S., Leclerc, M.,
Xu, T., Yue, L., and Poluektov, O.G., Phys. Chem.
Chem. Phys., 2013, vol. 15, pp. 9562–9574.
REFERENCES
1. Sidorov, L.N., Yurovskaya, M.A., Borshchevskii, A.Ya.,
Trushkov, I.V., and Ioffe, I.N., Fullereny. Uchebnoe
posobie (Fullerenes: A Textbook), Moscow: Izd. Ekza-
men, 2005.
Translated by I. Kudryavtsev
DOKLADY CHEMISTRY
Vol. 471
Part 1
2016