H. Shimakoshi et al. / Tetrahedron Letters 49 (2008) 6198–6201
6201
2
0. Mak, N.-K.; Kok, T.-W.; Wong, R.-N.-S.; Lam, S.-W.; Lau, Y.-K.; Leung, W.-N.;
Acknowledgments
Cheung, N.-H.; Huang, D. P.; Yeung, L.-L.; Chang, C. K. J. Biomed. Sci. 2003, 10,
4
18.
This study was partially supported by Grant-in-Aid for Scientific
Research on Priority Areas (452 and 460) and Global COE Program
21. Schere, K.; Abels, C.; Baumler, W.; Ackermann, G.; Szeimies, R. M. Arch.
Dematol. Res. 2004, 295, 535.
2
2. Kessel, D.; Conley, M.; Vicente, M. G. H.; Reiners, J. J., Jr. Photochem. Photobiol.
005, 81, 569.
3. Baba, T.; Shimakoshi, H.; Hisaeda, Y. Tetrahedron Lett. 2004, 45, 5973.
‘
Science for Future Molecular Systems’ from the Ministry of Educa-
2
tion, Culture, Sports, Science and Technology (MEXT) of Japan, and
Research for Promoting Technology Seeds (15-007) from the Japan
Science and Technology Agency (JST).
2
24. Baba, T.; Shimakoshi, H.; Endo, A.; Adachi, C.; Hisaeda, Y. Chem. Lett. 2008, 37,
64.
2
2
5. Shimakoshi, H.; Baba, T.; Iseki, Y.; Endo, A.; Adachi, C.; Hisaeda, Y. Chem.
Commun. 2008, 2882.
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6. Arnbjerg, J.; Jiménez-Banzo, A.; Paterson, M. J.; Nonell, S.; Borrell, J.;
Christiansen, O.; Ogilby, P. R. J. Am. Chem. Soc. 2007, 129, 5188.
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References and notes
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1
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DeRosa, M. C.; Crutchley, R. J. Coord. Chem. Rev. 2002, 233–234, 351.
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9. Compound 2: UV–vis (in CH
2 2
Cl ): [kmax/nm], 372, 383, 571, 616, 652; MALDI-
+
TOF-MS (6-aza-2-thiothimine matrix, m/z): [M+H] , 762.7; HR MS (ESI-TOF,
+
+
m/z): calcd for C41
0. The slide glass substrate was cleaned by sonication in a 30% H
H
60
N
5
O
5
SiS: [M+H] , 762.4084. Found: [M+H] , 762.4089.
aqueous
3
2 2
O
solution for 30 min followed by sonication in ethanol for 1 h at 303 K, and then
dried with nitrogen gas.
6
.
3
1. The sol–gel solution (10
00 rpm for 10 s (1st) and then 2000 rpm for 10 s (2nd).
2. The value was measured using an absolute photoluminescence quantum
lL) was placed on the glass substrate and spun at
1
87.
5
7
8
.
.
Nyman, E. S.; Hynninen, P. H. J. Photochem. Photobiol., B 2004, 73, 1.
Stockert, J. C.; Cañete, M.; Juarranz, A.; Horobin, R. W.; Borrell, J.; Teixidó, I.;
Nonell, S. Curr. Med. Chem. 2007, 14, 997.
Braslavsky, S. E.; Müller, M.; Mártire, D. O.; Pörting, S.; Bertolotti, S. G.;
Chakravorti, S.; Koc-Weier, G.; Knipp, B.; Schaffner, K. J. Photochem. Photobiol., B
3
U
f
efficiency measurement system (Hamamatsu C9920-02) incorporating an
integrating sphere. The gel film was deposited on a mica substrate.
9
.
À4
À9
3
3
3. [TMP] = 0.2 M (5.9 Â 10 mol), [porphycene] = 1.5 Â 10 mol (glass plate size
À10 2
0
.8 Â 2.5 cm with surface coverage 7.6 Â 10
2 2
mol/cm ), solvent 3 mL CH Cl
1
997, 40, 191.
in air at room temperature with a 500 W tungsten lamp (TOSHIBA Y-46 filter,
1
1
0. Vogel, E.; Bröring, M.; Weghorn, S. J.; Scholz, P.; Deponte, R.; Lex, J.; Schmickler,
H.; Schaffner, K.; Braslavsky, S. E.; Müller, M.; Pörting, S.; Fowler, C. J.; Sessler, J.
L. Angew. Chem., Int. Ed. 1997, 36, 1651.
k > 460 nm).
À6
4. [1,5-Dihydroxynaphthalene] = 3.3 mM (9.9 Â 10 mol), [porphycene] = 1.5 Â
À9
2
À10
10
mol (glass plate size 0.8 Â 2.5 cm with surface coverage 7.6 Â 10
mol/
1. Vogel, E.; Köcher, M.; Schmickler, H.; Lex, J. Angew. Chem., Int. Ed. Engl. 1986, 25,
cm ), solvent 3 mL CH
2
2
Cl :CH
3
OH (9:1, v/v) in air at room temperature with a
2
57.
500 W tungsten lamp (TOSHIBA Y-46 filter, k > 460 nm).
1
1
2. Sánchez-García, D.; Sessler, J. L. Chem. Soc. Rev. 2008, 37, 215.
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Schaffner, K.; Vogel, E. Photochem. Photobiol. 1986, 44, 555.
3
5. Suchard, O.; Kane, R.; Roe, B. J.; Zimmermann, E.; Jung, C.; Waske, P. A.; Mattay,
J.; Oelgemöller, M. Tetrahedron 2006, 62, 1467.
3
6. The oxygenated product, 5-hydroxy-1,4-naphthoquinone (Juglone); GC–MS
1
1
4. Guardiano, M.; Biolo, R.; Jori, G.; Schaffner, K. Cancer Lett. 1989, 44, 1.
5. Gottfried, V.; Davidi, R.; Averbuj, C.; Kimel, S. J. Photochem. Photobiol., B 1995,
+
(
(
EI, m/z): [M] , 174, UV–vis (kmax/nm), 427, 1H NMR (CDCl
3
, 500 MHz): d = 6.94
s, 2H), 7.27 (dd, 1H, Ph), 7.60–7.65 (m, 2H, Ph), 11.90 (s, 1H, OH).
30, 115.
3
3
7. The intensity of the UV–vis absorption at 651 nm of the gel film was monitored
during every run.
1
1
1
1
6. Villanueva, A.; Cañete, M.; Nonell, S.; Borrell, J. I.; Teixidó, J.; Junarranz, A. Anti-
Cancer Drug Des. 1996, 11, 89.
À6
À9
8. [1-Naphthol] = 3.3 mM (9.9 Â 10 mol), [porphycene] = 1.5 Â 10 mol (glass
7. Fickweiler, S.; Abels, C.; Karrer, S.; Bäumler, W.; Landthaler, M.; Hofstädter;
Szeimies, R. M. J. Photochem. Photobiol., B 1999, 48, 27.
8. Polo, L.; Segalla, A.; Beroloni, G.; Jori, G.; Schaffner, K.; Reddi, E. J. Photochem.
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À10
2
plate size 0.8 Â 2.5 cm with surface coverage 7.6 Â 10
mL CH Cl :CH OH (9:1, v/v) in air at room temperature with a 500 W
tungsten lamp (TOSHIBA Y-46 filter, k > 460 nm).
9. The oxygenated product, 1,4-naphthoquinone; GC–MS (EI, m/z): [M] , 158, UV–
vis (kmax/nm), 334, 1H NMR (CDCl
, 500 MHz): d = 6.96 (s, 2H), 7.74 (m, 2H, Ph),
.06 (m, 2H, Ph).
mol/cm ), solvent
3
2
2
3
+
3
9. Baumer, D.; Maier, M.; Engl, R.; Szeimies, R. M.; Bäumler, W. Chem. Phys. 2002,
3
285, 309.
8