˙
I. Gürol, M. Durmus, V. Ahsen
¸
FULL PAPER
[21] D. Atilla, M. Durmus¸, A. G. Gürek, V. Ahsen, T. Nyokong,
Dalton Trans. 2007, 12, 1235–1243.
[22] M. Durmus¸, T. Nyokong, Spectrochim. Acta Part A 2008, 69,
1170–1177.
[23] A. Ogunsipe, M. Durmus¸, D. Atilla, A. G. Gürek, V. Ahsen,
T. Nyokong, Synth. Met. 2008, 158, 839–847.
[24] J. Sleven, C. Görller, K. Binnemans, Mater. Sci. Eng. C 2001,
18, 229–238.
2,3-Octakis(2,2,3,3-tetrafluoropropoxy)phthalocyaninatozinc(II)
(6a): A mixture of 6 (250 mg, 0.64 mmol), anhydrous zinc(II) ace-
tate (30 mg, 0.16 mmol), n-amyl alcohol (10 mL) and DBU
(0.5 mL) were heated to reflux for 8 h under an argon atmosphere.
The resulting green suspension was cooled, the reaction mixture
was poured into an adequate amount of n-hexane, and the resulting
precipitate was collected. The crude product was dissolved in ace-
tone and was purified by passing through a silica gel column with
CH2Cl2/MeOH (10:1) elution. Yield 99 mg (38%) as a green pow-
[25] D. Masurel, C. Sirlin, J. Simon, New J. Chem. 1987, 11, 455–
456.
[26] N. Suzuki, U. S. Pat. Appl. Publ., 7,056,959 B2, 2004.
[27] M. Quintiliani, A. Kahnt, T. Wölfle, W. Hieringer, P. Vázquez,
A. Görling, D. M. Guldi, T. Torres, Chem. Eur. J. 2008, 14,
3765–3775.
[28] H. Uchida, H. Tanaka, H. Yoshiyama, P. Y. Reddy, S. Naka-
mura, T. Toru, Synlett 2002, 10, 1649–1652.
[29] R. Kenkyusho, Y. Akira, O. Yoshihito, Jap. Pat., 61-207461,A,
1986.
der; m.p. Ͼ200 °C. FTIR: νmax = 3045 (ArCH), 1600 (C=C), 1500,
˜
1
1460, 1380, 1110 (C–F) cm–1. H NMR ([D6]acetone): δ = 8.53 (s,
2
8 H, ArH), 6.89–6.68 (t, JH,F = 52 Hz, 8 H, CH), 5.14 (s, 16 H,
Ar-OCH2) ppm. 19F NMR (500 MHz, [D6]acetone): δ = –126.756
(m, 16 F, CF2), –140.903 (m, 16 F, CF2H) ppm. C56H32F32N8O8Zn
(1616.25): calcd. C 41.56, H 1.99, N 6.92; found C 41.19, H 1.84,
N 6.77. ESI-MS: m/z = 1617.2 [M + H]+.
[30] R. Kenkyusho, Y. Akira, O. Yoshihito, Jap. Pat., 61-207431,A,
1986.
[31] N. Muller, J. Pharm. Sci. 1986, 75, 987–991.
[32] M. J. Stillman, T. Nyokong in Phthalocyanines: Properties and
Applications (Eds.: C. C. Leznoff, A. B. P. Lever), VCH Pub-
lishers, New York, 1989, vol. 1, p. 133.
[33] H. Enkelkamp, R. J. M. Nolte, J. Porphyrins Phthalocyanines
2000, 4, 454–459.
[34] D. D. Dominquez, A. W. Snow, J. S. Shirk, R. G. S. Pong, J.
Porphyrins Phthalocyanines 2001, 7, 582–592.
[35] T. Nyokong, H. Isago, J. Porphyrins Phthalocyanines 2004, 8,
1083–1090.
2,3-Octakis(propoxy)phthalocyaninatozinc(II) (7a): Compound 7a
was prepared according to the procedure described in the litera-
ture.[24,25]
[1] C. C. Leznoff, A. B. P Lever (Eds.), Phthalocyanines, Properties
and Applications, VCH Publishers, New York, 1989, vols. 1–4.
[2] K. Kasuga, H. Hayashi, M. Handa, Chem. Lett. 1991, 11,
1877–1880.
[3] D. Wöhrle, V. Schmidt, J. Chem. Soc., Dalton Trans. 1988, 2,
549–551.
[4] a) P. A. Bernstein, A. B. P. Lever, Inorg. Chem. 1990, 29, 608–
616; b) G. Fu, Y. Fu, K. Jayaraj, A. B. P. Lever, Inorg. Chem.
1990, 29, 4090–4095.
[36] A. C. Beveridge, B. A. Bench, S. M. Gorun, G. J. Diebold, J.
Phys. Chem. A 2003, 107, 5138–5143.
[5] a) D. Wöhrle, G. Meyer, B. Wahl, Makromol. Chem. 1980, 181,
2127–2135; b) A. Giraudeau, A. Louati, M. Gross, J. J. Andre,
J. Simon, C. H. Su, K. M. Kadish, J. Am. Chem. Soc. 1983,
105, 2917–2919; c) A. Louati, M. El Meray, J. J. Andre, J. Si-
mon, K. M. Kadish, M. Gross, A. Giraudeau, Inorg. Chem.
1985, 24, 1175–1779.
[37] H. Du, R. A. Fuh, J. Li, A. Corkan, J. S. Lindsey, Photochem.
Photobiol. 1998, 68, 141–142.
[38] D. Maree, T. Nyokong, K. Suhling, D. Phillips, J. Porphyrins
Phthalocyanines 2002, 6, 373–376.
[39] D. D. Perrin, W. L. F. Armarego, Purification of Laboratory
Chemicals, 2nd ed., Pegamon Press, Oxford, 1989.
[40] R. D. George, A. W. Snow, J. Heterocycl. Chem. 1995, 32, 495–
498.
[6] M. N. Golovin, P. Seymour, K. Jayaraj, Y. Fu, A. B. P. Lever,
Inorg. Chem. 1990, 29, 1719–1727.
[7] S. Wie, D. Huang, L. Li, Q. Meng, Dyes Pigm. 2003, 56, 1–6.
[8] L. Gao, X. Qian, Dyes Pigm. 2001, 51, 51–55.
[9] T. Sugimori, S. Horike, M. Handa, K. Kasuga, Inorg. Chim.
Acta 1998, 278, 253–255.
[10] C. C. Leznoff, J. L. S. Sanchez, Chem. Commun. 2004, 3, 338–
339.
[11] N. V. Kondratenko, V. N. Nemykin, E. A. Lukyanets, N. A.
Kostromina, S. V. Volkov, L. M. Yagupolskii, J. Porphyrins
Phthalocyanines 1997, 1, 341–347.
[12] a) H. Miyoshi, T. Tanaka, Y. Ueda, Jap. Pat. 63-313760,A,
1988; b) H. Miyoshi, T. Tanaka, Y. Ueda, Jap. Pat. 63-
312364,A, 1988.
[41] J. G. Young, W. Onyebuage, J. Org. Chem. 1990, 55, 2155–2159.
[42] D. Wöhrle, M. Eskes, K. Shigehara, A. Yamada, Synthesis
1993, 2, 194–196.
[43] S. Fery-Forgues, D. Lavabre, J. Chem. Educ. 1999, 76, 1260–
1264.
[44] I. Seotsanyana-Mokhosi, N. Kuznetsova, T. Nyokong, J. Pho-
tochem. Photobiol. A: Chem. 2001, 140, 215–222.
[45] A. Ogunsipe, T. Nyokong, J. Mol. Struct. 2004, 689, 89–97.
[46] N. Kuznetsova, N. Gretsova, E. Kalmkova, E. Makarova, S.
Dashkevich, V. Negrimovskii, O. Kaliya, E. Luk’yanets, Russ.
J. Gen. Chem. 2000, 70, 133–140.
[47] J. Rose, Advanced Physico-chemical Experiments, 1st ed., Sir
Isaac Pitman & Sons Ltd., London, 1964, p. 257.
[48] M. Sakamoto, Jap. Pat., JP 07246775 A 1995.
[49] W. O. Siegl, J. Heterocycl. Chem. 1981, 18, 1613–1618.
[50] K. Kasuga, M. Kawashima, K. Asano, T. Sugimori, K. Abe,
T. Kikkawa, T. Fujiwara, Chem. Lett. 1996, 10, 867–868.
[51] N. Kobayashi, H. Ogata, N. Nonaka, E. A. Luk’yanets, Chem.
Eur. J. 2003, 9, 5123–5134.
[13] J. Griffiths, J. Schofield, M. Wainwright, S. B. Brown, Dyes
Pigm. 1997, 33, 65–78.
[14] T. J. Dougherty, Photochem. Photobiol. 1993, 58, 895–900.
[15] A. Hsi, D. I. Rosenthal, E. Glatstein, Drugs 1999, 57, 725–734.
[16] I. Rosenthal, Photochem. Photobiol. 1991, 53, 859–870.
[17] Q. Peng, J. Moan, Br. J. Cancer 1995, 72, 565–574.
[18] R. W. Boyle, J. Rousseau, S. V. Kudrevich, Br. J. Cancer 1996,
73, 49–53.
[19] T. Qiu, X. Xu, J. Liu, X. Qian, Dyes Pigm. 2009, 83, 127–133.
[20] I. Gürol, M. Durmus¸, V. Ahsen, T. Nyokong, Dalton Trans.
2007, 34, 3782–3791.
[52] D. Wöhrle, G. Schnurfeil, G. Knothe, Dyes Pigm. 1992, 18, 91–
102.
Received: November 12, 2009
Published Online: February 3, 2010
1230
www.eurjic.org
© 2010 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim
Eur. J. Inorg. Chem. 2010, 1220–1230