chloroform–methanol = 8 : 1 ꢂ 9; 27: chloroform–methanol =
8 : 1 ꢂ 5; 28: chloroform–methanol = 8 : 1 ꢂ 3) to afford
compound 24, 25, 26, 27 and 28 as a purple solid. The physical
and spectral data are shown below.
109, 3907; (b) K. Hara, M. Kurashige, Y. Dan-oh, C. Kasada,
A. Shinpo, S. Suga, K. Sayama and H. Arakawa, New J.
Chem., 2003, 27, 783; (c) K. Hara, K. Sayama, Y. Ohga,
A. Shinpo, S. Suga and H. Arakawa, Chem. Commun., 2001,
569.
2 (a) T. Dentani, K. Nagasaka, K. Funabiki, J.-Y. Jin, T. Yoshida,
H. Minoura and M. Matsui, Dyes Pigm., 2008, 77, 59;
(b) Q.-H. Yao, L. Shan, F.-Y. Li, D.-D. Yin and C.-H. Huang,
New J. Chem., 2003, 27, 1277; (c) Z.-S. Wang, F.-Y. Li and
C.-H. Huang, J. Phys. Chem. B, 2001, 105, 9210; (d) Z.-S. Wang,
F.-Y. Li, C.-H. Huang, L. Wang, M. Wei, L.-P. Jim and N.-Q. Li,
J. Phys. Chem. B, 2000, 104, 9676; (e) Z.-S. Wang, F.-Y. Li and
C.-H. Huang, Chem. Commun., 2000, 2063.
3 (a) R. Chen, X. Yang, H. Tian and L. Sun, J. Photochem. Photo-
biol., A, 2007, 189, 295; (b) M. Liang, W. Xu, F. Cai, P. Chen,
B. Peng, J. Chen and Z. Li, J. Phys. Chem. C, 2007, 111, 4465;
(c) H. Choi, J.-K. Lee, K.-J. Song, K. Song, S. O. Kang and J. Ko,
Tetrahedron, 2007, 63, 1553; (d) N. Koumura, Z.-S. Wang,
S. Mori, M. Miyashita, E. Suzuki and K. Hara, J. Am. Chem.
Soc., 2006, 128, 14256; (e) S. Kim, J. K. Lee, S. O. Kang, J. Ko,
J.-H. Yum, S. Fantacci, F. D. Angelis, D. D. Censo,
24. Yield 89%, mp 175–178 1C. dH (400 MHz, DMSO-d6,
Me4Si): 1.29–1.33 (1 H, m), 1.59–1.68 (2 H, m), 1.81–1.84
(2 H, m), 2.00–2.05 (1 H, m), 3.81–3.85 (1 H, m), 4.69 (2 H, s),
4.84–4.88 (1 H, m), 6.95 (1 H, d, J = 8.5 Hz), 7.01 (2 H, d, J =
8.3 Hz), 7.06 (1 H, s), 7.09 (2 H, d, J = 8.3 Hz), 7.19–7.21
(2 H, m), 7.28–7.34 (5 H, m), 7.39–7.49 (4 H, m), 7.57–7.58
(2 H, m), 7.77 (1 H, d, J = 3.9 Hz) and 8.10 (1 H, s). m/z
(FAB) = 697.1647 (MH+, C41H33N2O3S3 requires 697.1653).
25. Yield 31%, mp 4 300 1C. dH (400 MHz, DMSO-d6,
Me4Si): 1.14 (3 H, t, J = 6.9 Hz), 1.25–1.37 (1 H, m),
1.60–1.68 (2 H, m), 1.80–1.84 (2 H, m), 2.01–2.08 (1 H, m),
3.82–3.86 (1 H, m), 3.98–4.00 (2 H, m), 4.69 (2 H, s), 4.84–4.87
(1 H, m), 6.96 (1 H, d, J = 8.5 Hz), 7.00 (2 H, d, J = 9.3 Hz),
7.07 (1 H, s), 7.08 (2 H, d, J = 9.3 Hz), 7.20–7.55 (13 H, m),
7.68 (1 H, d, J = 3.9 Hz) and 8.02 (1 H, s). m/z (FAB) =
824.1757 (MH+, C46H38N3O4S4 requires 824.1745).
M. K. Nazeeruddin and M. Gratzel, J. Am. Chem. Soc., 2006,
¨
128, 16701; (f) D. P. Hagberg, T. Edvinsson, T. Marinado,
G. Boschloo, A. Hagfeldt and L. Sun, Chem. Commun., 2006,
2245; (g) K. Hara, T. Sato, R. Katoh, A. Furube, T. Yoshihara,
M. Murai, M. Kurashige, S. Ito, A. Shinpo, S. Suga and
H. Arakawa, Adv. Funct. Mater., 2005, 15, 246; (h) T. Kitamura,
M. Ikeda, K. Shigaki, T. Inoue, N. A. Anderson, X. Ai, T.-Q. Lian
and S. Yanagida, Chem. Mater., 2004, 16, 1806; (i) K. Hara,
M. Kurashige, S. Ito, A. Shinpo, S. Suga, K. Sayama and
H. Arakawa, Chem. Commun., 2003, 252.
4 (a) D. Kim, J.-K. Lee, S. O. Kang and J. Ko, Tetrahedron, 2007,
63, 1913; (b) I. Jung, J.-K. Lee, K.-H. Song, K. Song, S. O. Kang
and J. Ko, J. Org. Chem., 2007, 72, 3652; (c) S. Kim, J.-K. Lee,
S. O. Kang, J. Ko, J.-H. Yum, S. Fantacci, F. D. Angelis,
26. Yield 81%, mp 4 300 1C. dH (400 MHz, DMSO-d6,
Me4Si): 1.24–1.29 (1 H, m), 1.25 (18 H, s), 1.59–1.87 (2 H, m),
1.85–1.87 (2 H, m), 2.01–2.09 (1 H, m), 3.83–3.87 (1 H, m),
4.61 (2 H, s), 4.85–4.88 (1 H, m), 5.19 (2 H, s), 6.98 (1 H, d,
J = 8.5 Hz), 7.00 (2 H, d, J = 8.8 Hz), 7.07 (1 H, m), 7.10 (2 H,
d, J = 8.8 Hz), 7.19–7.48 (14 H, m), 7.53 (1 H, s), 7.57 (1 H, d,
J = 3.9 Hz), 7.72 (1 H, d, J = 4.1 Hz) and 8.07 (1 H, s). m/z
(FAB) = 998.3133 (MH+, C59H56N3O4S4 requires 998.3154).
D. D. Censo, M. K. Nazeeruddin and M. Gratzel, J. Am. Chem.
Soc., 2006, 128, 16701.
¨
5 (a) S. Ito, S. M. Zakeeruddin, R. Humphry-Baker, P. Liska,
R. Charvet, P. Comte, M. K. Nazeeruddin, P. Pechy,
27. Yield 95%, mp 4 300 1C. dH (400 MHz, DMSO-d6,
Me4Si): 1.22–1.35 (1 H, m), 1.23 (18 H, s), 1.57–1.66 (2 H, m),
1.78–1.85 (2 H, m), 1.95–2.05 (1 H, m), 3.73–3.79 (1 H, m),
4.33 (2 H, s), 4.74–4.78 (1 H, m), 5.10 (2 H, s), 6.91 (1 H, d,
J = 8.5 Hz), 6.99 (2 H, d, J = 8.3 Hz), 7.03 (1 H, s), 7.04
(2 H, d, J = 8.3 Hz), 7.17–7.54 (18 H, m), 7.62 (1 H, s) and
7.94 (1 H, s). m/z (FAB) = 1080.3016 (MH+, C63H58N3O4S5
requires 1080.3031).
M. Takata, H. Miura, S. Uchida and M. Gratzel, Adv. Mater.,
¨
2006, 18, 1202; (b) L. Schmidt-Mende, U. Bach, R. Humphry-
Baker, T. Horiuchi, H. Miura, S. Ito, S. Uchida and M. Gratzel,
¨
Adv. Mater., 2005, 17, 813; (c) T. Horiuchi, H. Miura and
S. Uchida, J. Photochem. Photobiol., A, 2004, 164, 29;
(d) T. Horiuchi, H. Miura, K. Sumioka and S. Uchida, J. Am.
Chem. Soc., 2004, 126, 12218; (e) T. Horiuchi, H. Miura and
S. Uchida, Chem. Commun., 2003, 3036; (f) W. H. Howie,
F. Claeyssens, H. Miura and L. M. Peter, J. Am. Chem. Soc.,
2008, 130, 1367.
6 A. Otsuka, K. Funabiki, N. Sugiyama, T. Yoshida, H. Minoura
and M. Matsui, Chem. Lett., 2006, 35, 666.
7 P. Y. Reddy, L. Giribabu, C. Lyness, H. J. Snaith, C. Vijaykumar,
M. Chandrasekharam, M. Lakshmikantam, J.-H. Yum,
K. Kalyanasundaram, M. Gratzel and M. K. Nazeeruddin, Angew.
¨
Chem., Int. Ed., 2007, 46, 373.
8 M. Matsui, Y. Hashimoto, K. Funabiki, J. Y. Jin, T. Yoshida and
H. Minoura, Synth. Met., 2005, 148, 147.
9 K. Hara, T. Sato, R. Katoh, A. Furube, Y. Ohga, A. Shinpo,
S. Suga, K. Sayama, H. Sugihara and H. Arakawa, J. Phys. Chem.
B, 2003, 107, 597.
28. Yield 32%, mp 4 300 1C. dH (400 MHz, DMSO-d6,
Me4Si): 1.22–1.33 (1 H, m), 1.26 (18 H, s), 1.59–1.68 (2 H, m),
1.80–1.84 (2 H, m), 1.97–2.03 (1 H, m), 3.78–3.83 (1 H, m),
4.46 (2 H, s), 4.77–4.81 (1 H, m), 5.17 (2 H, s), 6.96 (1 H, d,
J = 8.5 Hz), 6.98 (2 H, d, J = 9.1 Hz), 7.05 (1 H, s), 7.06
(2 H, d, J = 9.1 Hz), 7.19–7.54 (20 H, m), 7.71 (1 H, s) and
8.02 (1 H, s). m/z (FAB) = 1162.2795 (MH+, C67H60N3O4S6
requires 1162.2908).
10 T. Yoshida, M. Iwaya, H. Ando, T. Oekermann, K. Nonomura,
D. Schlettwein, D. Wohrle and H. Minoura, Chem. Commun.,
2004, 400.
11 R. Katoh, A. Furube, T. Yoshihara, K. Hara, G. Fujihashi,
S. Takano, S. Murata, H. Arakawa and M. Tachiya, J. Phys.
Chem. B, 2004, 108, 4818.
Acknowledgements
¨
This work was financially supported in part by Grants-in-Aid
for Science Research (no. 19550185) from the Japan Society
for the Promotion of Science (JSPS).
12 J. D. Mee, US Pat., 5679795, 1997.
´
13 G. Bidan, A. De Nicola, V. Enee and S. Guilerez, Chem. Mater.,
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14 M. Matsui, M. Wang, K. Funabiki, Y. Hayakawa and
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