1338
LERMONTOVA et al.
Ytterbium tetra(2,6-dimethylphenyl)tetracyano-
Research (projects 16-34-60117-mol_a_dk, 16-04-
01676-a, 15-02-05468-a, 15-02-05189-a, and 14-02-
00753-a) and the Ministry of Education and Science of
the Russian Federation (project 14.Z50.31.022).
porphyrazinate (2g) was prepared similarly. Yield
42%. IR spectrum, ν, cm–1: 2197 (С≡N), 1652, 15602,
1569, 1495 (C=N, C=C), 905, 817, 771, 747, 705
(C–HAr). Found, %: C 57.55; H 3.43; N 16.51; Yb
17.60. C48H33N12O3Yb. Calculated, %: C 57.71; H
3.33; N 16.83; Yb 17.32.
REFERENCES
1. Trivedi, E.R., Harney, A.S., Olive, M.B., Podgorski, I.,
Moin, K., Sloane, B.F., Barrett, A.G.M., Meade, T.J.,
and Hoffman, B.M., Proc. Natl. Acad. Sci. USA., 2010,
vol. 107, p. 1284. DOI: 10.1073/pnas.0912811107.
2. Bonnett, R., Chemical Aspects of Photodynamic
Therapy, Amsterdam: Gordon and Breach Science
Publishers, 2000.
3. Klapshina, L.G., Grigoryev, I.S., Douglas, W.E.,
Trifonov, A.A., Gudilenkov, I.D., Semenov, V.V.,
Bushuk, B.A., and Bushuk, S.B., Chem. Commun.,
2007, vol. 19, p. 1942. DOI: 10.1039/b701994g.
4. Klapshina, L.G., Douglas, W.E., Grigoryev, I.S.,
Korytin, A.I., Lavrentiev, S.A., Lopatin, M.A.,
Lukyanov, A.Yu., Semenov, V.V., Gerbier, P., and
Treushnikov, V.M., J. Mater. Chem., 2009, vol. 19,
p. 3668. DOI: 10.1039/b821667c.
Tetra(2-naphthyl)tetracyanoporphyrazine (3d).
Ytterbium tetra(2-napthyl)tetracyanoporphyrazinate 2d
(0.2 g, 0.22 mmol) was dissolved in 2 mL of
trifluoroacetic acid and stirred during 30 min at room
temperature. About 30 mL of water was then added;
the precipitate was centrifuged off and washed with
water till neutral reaction. The product was purified by
column chromatography (silica gel 60, 40–60 µm,
THF as eluent). Yield 38%. IR spectrum, ν, cm–1: 3443
(N–H), 2200 (С≡N), 1595, 1508, 1496, 1469, 1451,
1435 (C=C, C=N), 902, 864, 839, 814, 749, 617
(C–HAr). Mass spectrum, m/z 918 [М]+. Found, %: C
78.78; H 3.19; N 18.03. C60H30N12. Calculated, %: C
78.42; H 3.29; N 18.29.
5. Harvey, M.D., Pace, J.T., and Yee, G.T., Polyhedron.,
2007, vol. 26, p. 2037. DOI: 10.1016/j.poly.2006.09.097.
6. Miller, J.S., Angew. Chem. Int. Ed., 2006, vol. 45,
p. 2508. DOI: 10.1002/anie.200503277.
Tetra(pentafluorophenyl)tetracyanoporphy-
razine (3c) was prepared similarly. Yield 33%. IR
spectrum, ν, cm–1: 3460 (N–H), 2207 (С≡N), 1650,
1523, 1501, 1468, 1414 (C=C, C=N). Mass spectrum,
m/z: 1078 [М]+. Found, %: C 49.55; H 0.21; F 34.78;
N 15.46. C44H2F20N12. Calculated, %: C 49.00; H 0.19;
F 35.23; N 15.58.
7. Haidekker, M.A. and Theodorakis, E.A., J. Biol. Eng.,
2010, vol. 4, p. 11. DOI: 10.1186/1754-1611-4-11.
8. Forster, T. and Hoffmann, G., J. Phys. Chem., 1971,
vol. 75, p. 63. DOI: 10.1524/zpch.1971.75.1_2.063.
9. Izquierdo, M.A., Vysniauskas, A., Lermontova, S.A.,
Grigoryev, I.S., Shilyagina, N.Y., Balalaeva, I.V.,
Klapshina, L.G., and Kuimova, M.K., J. Mater. Chem.
(B), 2015, vol. 3, p. 1089. DOI: 10.1039/c4tb01678e.
10. Kuimova, M.K., Chimia, 2012, vol. 66, p. 159. DOI:
10.2533/chimia.2012.159.
Tetra(4-biphenyl)tetracyanoporphyrazine (3e) was
prepared similarly. Yield 35 %. IR spectrum, ν, cm–1:
3422 (N–H), 2201 (С≡N), 1603, 1558, 1499 (C=C,
C=N), 906, 855, 823, 765, 750, 738, 698 (C–HAr).
Mass spectrum, m/z: 1022 [М]+. Found, %: C 79.42; H
3.84; N 16.74. C68H38N12. Calculated, %: C 79.83; H
3.74; N 16.43.
11. Smith, A.M., Mancini, M.C., and Nie, Sh., Nat.
Nanotechnol., 2009, vol. 4, p. 710. DOI: 10.1038/
nnano.2009.326.
12. Weissleder, R., Nat. Biotechnol., 2001, vol. 19, p. 316.
DOI: 10.1038/86684.
13. Shilyagina, N.Yu., Plekhanov, V.I., Shkunov, I.V.,
Shilyagin, P.A., Dubasova, L.V., Brilkina, A.A.,
Sokolova, E.A., Turchin, I.V., and Balalaeva, I.V., Sovr.
Tekhnol. Med., 2014, vol. 6, no. 2, p. 15.
14. Freshney, R., Culture of Animal Cells, Wiley, 2005.
15. Gudilenkov I.D., Fukin, G.K., Baranov, E.V., and
Trifonov, A.A., Russ. Chem. Bull., 2008, vol. 57, p. 40.
DOI: 10.1007/s11172-008-0006-y.
Tetra(2,6-dimethylphenyl)tetracyanoporphy-
razine (3g) was prepared similarly. Yield 30%. IR
spectrum, ν, cm–1: 3426 (N–H), 2193, 2227 (С≡N),
1613, 1567, 1555, 1505 (C=C, C=N), 906, 796, 777,
753, 688, 675 (C–HAr). Mass spectrum, m/z: 830 [М]+.
Found, %: C 75.55; H 4.70; N 19.75. C52H38N12.
Calculated, %: C 75.16; H 4.61; N 20.23.
ACKNOWLEDGMENTS
16. Yakimansky, A.V., Meleshko, T.K., Ilgach, D.M.,
Bauman, M.A., Anan’eva, T.D., Klapshina, L.G.,
Lermontova, S.A., Balalaeva, I.V., and Douglas, W.E.,
J. Polym. Sci. (A), 2013, vol. 51, p. 4267. DOI: 10.1002/
pola.26846.
Authors are grateful to M.K. Kuimova et al.
(Department of Chemistry, Imperial College, London)
for the assistance with the experiments. This work was
financially supported by Russian Foundation for Basic
RUSSIAN JOURNAL OF GENERAL CHEMISTRY Vol. 86 No. 6 2016