5662
X. Liu et al. / Tetrahedron 61 (2005) 5655–5662
8
.82–8.89 (m, 8H, H , H
3
0
, H , H
4
0
, H , H
9
0
, H , H ),
0
10
3. (a) Bennett, I. M.; Vanegas Farfano, H. M.; Bogani, F.;
Primak, A.; Liddell, P. A.; Otero, L.; Sereno, L.; Silber, J. J.;
Moore, A. L.; Moore, T. A.; Gust, D. Nature 2002, 420,
398–400. (b) Wasielewski, M. R. Chem. Rev. 1992, 92,
435–461. (c) Choi, M. S.; Aida, T.; Yamazaki, T.; Yamazaki,
I. Angew. Chem., Int. Ed. Engl. 2001, 40, 3194–3198. (d)
Linke, M.; Chambron, J. C.; Heitz, V.; Sauvage, J. P.; Encinas,
S.; Barigelletti, F.; Flamigni, L. J. Am. Chem. Soc. 2000, 122,
11834–11844. (e) Tour, J. M. Chem. Rev. 1996, 96, 537–554.
4. (a) Burrell, A. K.; Officer, D. L.; Reid, D. C. W. Angew.
Chem., Int. Ed. Engl. 1995, 34, 900–902. (b) Rodriguez, J.;
Kirmaier, C.; Johnson, M. R.; Friesner, R. A.; Holten, D.;
Sessler, J. L. J. Am. Chem. Soc. 1991, 113, 1652–1659. (c)
Sessler, J. L.; Wang, B.; Harriman, A. J. Am. Chem. Soc. 1995,
117, 704–714. (d) Harriman, A.; Kubo, Y.; Sessler, J. L. J. Am.
Chem. Soc. 1992, 114, 388–390. (e) Luo, C.; Guldi, D. M.;
Imahori, H.; Tamaki, K.; Sakata, Y. J. Am. Chem. Soc. 2000,
3
4
9
10
9
amide-H); C NMR (CD CN): d 13.9, 21.3, 31.3, 34.9,
.09–9.13 (m, 5H, H , H , H
0
, H , H ), 9.56 (s, br, 1H,
0
19
1
3
16
16
19
1
3
3
6
1
1
1
1
3.3, 119.3, 120.6, 121.5, 122.7, 123.8, 123.9, 124.3, 125.7,
26.5, 127.1, 129.5, 130.6, 131.3, 131.8, 131.9, 134.4,
35.3, 137.8, 138.2, 138.9, 139.0, 139.8, 139.9, 144.3,
51.1, 151.5, 152.2, 153.0, 153.2, 153.3, 153.5, 155.9,
57.7, 157.9, 162.6, 163.7.); UV–vis in methylene chloride
lmax [nm]Z421.0, 450.0, 555.0, 650.0; API-ES-MS m/z:
C
2C
[
M-PF6]
1840.6, [M-2PF6]
847.4; Anal. Calcd for
C100H F N O P Ru$1.5CH Cl : C, 57.69; H, 4.67; N,
.29. Found: C, 57.56; H, 4.99; N, 6.95.
95
12 11
9
2
2
2
7
3
[
0
.1.5. Zn-Porphyrin-NHCO-bpy-Ru[(bpy)(COOEt) ] -
2
PF6] (5-Zn). A solution of Zn(OAc) $2H O (10 mg,
2 2 2
2
.050 mmol) in ethanol (1 mL) was added to a solution of 5
50 mg, 0.025 mmol) in chloroform (10 mL), and stirred at
(
rt overnight under N in the dark. This mixture was washed
2
1
22, 6535–6551.
with water and then evaporated to dryness and purified by
CH Cl /MeOH (10:1). The desired product was obtained as
a red-brown solid: (49 mg, 95%) mp O250 8C; H NMR
CD CN) d 1.42–1.45 (m, 12H, –COOCH CH ), 1.56 (s,
3 2 3
H, tert-butyl), 1.58 (s, 18H, tert-butyl), 2.64 (s, 3H, bpy-
5
. (a) Speck, M.; Kurreck, H.; Senge, M. O. Eur. J. Org. Chem.
2
2
2000, 12, 2303–2314. (b) Ward, M. D. Chem. Soc. Rev. 1997,
26, 365–375. (c) Hombrecher, H. K.; Ludtke, K. Tetrahedron
1993, 49, 9489–9494. (d) Bens, A. T.; Frewert, D.; Kodatis,
1
(
9
K.; Kryschi, C.; Martin, H. D.; Trommsdorff, H. P. Eur. J. Org.
Chem. 1998, 11, 2333–2338. (e) Myles, A. J.; Branda, N. R.
Tetrahedron Lett. 2000, 41, 3785–3788.
CH ), 4.47–4.51 (m, 8H, –COOCH CH ), 7.37 (d, JZ
3
2
3
5
.2 Hz, 1H, H14
0
0
), 7.56–7.59 (m, 1H, H15 ), 7.73–7.78 (m,
0
6
H ), 7.92–8.04 (m, 8H, H , H
H, H , H
, H , H
0
, H , H
0
), 7.86–7.90 (m, 2H, H14,
0
7
7
8
8
12
12
6
. Balzani, V.; Carassiti, V. Photochemistry of Coordination
Compound; Acadamic: New York, 1970.
, H , H
18
0
, H , H , H ,
0
1
5
17
17
18
20
20 21
H21
8
8
0
), 8.06–8.15 (m, 8H, H , H
1
0
H , H
5
0
, H , H
6
0
, H , H ),
0
1
5
6
11
11
7
. Sauvage, J. P.; Collin, J. P.; Chambron, J. C.; Guillerez, S.;
Coudert, C.; Balzani, V.; Barigelletti, F.; De Cola, L.;
Flamigni, L. Chem. Rev. 1994, 94, 993–1019.
.26 (d, JZ7.6 Hz, 2H, H ,H
0
), 8.68 (s, 1H, H13
, H , H ), 9.06–9.13
0
), 8.83–
2
2
.89 (m, 8H, H , H
0
, H , H
0
0
, H , H
9
0
0
10
3
3
4
4
9
10
(
m, 5H, H , H , H
1
, H , H ), 9.49 (s, br, 1H, amide-H);
0
19
C NMR (CD CN) d 14.4, 21.4, 31.8, 35.3, 63.8, 118.3,
3
3
16
16
19
1
3
8. LeGourri e´ rec, D.; Andersson, M.; Davidsson, J.; Mukhtar, E.;
Sun, L.; Hammarstr o¨ m, L. J. Phys. Chem. A 1999, 103,
5
1
1
1
1
1
19.4, 120.6, 121.7, 123.1, 124.2, 124.3, 124.9, 126.1,
26.9, 127.7, 130.1, 132.3, 132.6, 135.1, 135.8, 138.2,
40.3, 140.4, 140.9, 141.2, 144.5, 150.7, 150.9, 151.2,
52.0, 152.8, 153.5, 153.8, 153.9, 154.2, 156.5, 158.3,
58.5, 163.1, 164.4; UV–vis in methylene chloride lm Ca x
57–559.
9
. (a) Benniston, A. C.; Chapman, G. M.; Harriman, A.; Mehrabi,
M. J. Phys. Chem. A 2004, 108, 9026–9036. (b) Lintuluoto,
J. M.; Borovkov, V. V.; Hembury, G. A.; Inoue, Y. Bull.
Chem. Soc. Jpn. 2003, 76, 309. (c) Hamachi, I.; Tsukiji, S.;
Shinkai, S.; Oishi, S. J. Am. Chem. Soc. 1999, 121, 5500–5506.
[
nm]Z422.0, 549.0, 468.0. API-ES-MS m/z: [M-PF ]
6
2C
904.7, [M-2PF6] , 879.0 Anal. Calcd for C100H F -
1
N O P RuZn$1.2CH Cl : C, 56.50; H, 4.47; N, 7.16.
93 12
(
d) Flamigni, L.; Barigelletti, F.; Armaroli, N.; Ventura, B.;
Collin, J. P.; Sauvage, J. P.; Williams, J. A. G. Inorg. Chem.
999, 38, 661–667. (e) Harriman, A.; Hissler, M.; Trompette,
1
1
9
2
2
2
Found: C, 56.85; H, 4.51; N, 6.78.
1
O.; Ziessel, R. J. Am. Chem. Soc. 1999, 121, 2516–2525. (f)
Hamachi, I.; Tanaka, S.; Tsukiji, S.; Shinkai, S.; Oishi, S.
Inorg. Chem. 1998, 37, 4380–4388.
Acknowledgements
Financial support of this work from the following sources is
gratefully acknowledged: The Swedish Energy Agency and
Swedish Research Council (VR), China Natural Science
Foundation (Grant 20128005), the Ministry of Science and
Technology (MOST) (Grant 2001CCA02500) and the
Ministry of Education. The authors thank Ms. Rong Zhang
and Ms. Xin-Mei Fu for MS measurements, and Dr. Tom a´ sˇ
Pol ´ı vka, Lund University, Sweden for helpful discussion.
10. Saji, T.; Aoyagui, S. J. Electroanal. Chem. 1975, 58, 401–407.
11. Lindsey, J. S.; Schreiman, I. C.; Hsu, H. C.; Kearney, P. C.;
Marguerettaz, A. M. J. Org. Chem. 1987, 52, 827–836.
12. Hunter, C. A.; Sarson, L. D. Angew. Chem., Int. Ed. Engl.
1994, 33, 2313–2316.
13. James, L.; Graff, T. J.; Sobieralski, M.; Gregory, S. W.;
Geoffroy, L. J. Am. Chem. Soc. 1982, 104, 7526–7533.
14. Lintuluoto, J. M.; Borovkov, V. V.; Inoue, Y. Tetrahedron
Lett. 2000, 41, 4781–4786.
1
5. Strouse, G. F.; Anderson, P. A.; Schoonover, J. R.; Meyer,
T. J.; Keene, F. R. Inorg. Chem. 1992, 31, 3004–3006.
16. Gabrielsson, A.; Hartl, T.; Smith, R. L.; Lindsay, J. S. Chem.
Commun. 2002, 9, 950–951.
References and notes
1
2
. Komatsu, T.; Moritake, M.; Tsuchida, E. Chem. Eur. J. 2003,
, 4626–4633.
17. Sessler, J. L.; Capuano, V. L.; Burrell, A. K. Inorg. Chim. Acta
1993, 204, 93–101.
9
. Staab, H. A.; Weikard, J.; R u¨ ckemann, A.; Schw o¨ gler, A. Eur.
J. Org. Chem. 1998, 12, 2703–2711.
18. Tokel-Takvoryan, N. E.; Hemingway, R. E.; Bard, A. J. J. Am.
Chem. Soc. 1973, 95, 6582–6589.