Photoaddition of water and alcohols to the anthracene moiety of 9-(2′-hydroxyphenyl)anthracene via formal excited state intramolecular proton transfer

Journal of the American Chemical Society

Volumn 126, Issue 25, 2004, Pages 7890-7897

  Flegel, Mitchel ^a   Lukeman, Matthew ^a   Huck, Lawrence ^a   Wan, Peter ^a  

^a UNIVERSITY OF VICTORIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

ETHERS; PHOTOLYSIS; REACTION KINETICS; SENSITIVITY ANALYSIS;

PHOTOADDITION; PROTON TRANSFER;

ALCOHOLS;

2 QUINONE METHIDE; 9 (2' HYDROXYPHENYL)ANTHRACENE; ALCOHOL; ANTHRACENE; DEUTERIUM OXIDE; HYDROXYL GROUP; PHENOL DERIVATIVE; QUINONE DERIVATIVE; SOLVENT; TRIPHENYLMETHYL ETHER; TRITANOL; UNCLASSIFIED DRUG; WATER;

ADDITION REACTION; ARTICLE; CHEMICAL COMPOSITION; CHEMICAL REACTION; EXCITED STATE INTRAMOLECULAR PROTON TRANSFER; IRRADIATION; LASER; NANOSECOND LASER FLASH PHOTOLYSIS; PHOTOADDITION; PHOTOCHEMISTRY; PHOTOLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT; QUANTUM CHEMISTRY; REACTION ANALYSIS;

EID: 3042690038     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja039078g     Document Type: Article

References (32)

1. Weller, K. Naturwissenschaften 1955, 42, 175.
2. For reviews of ESIPT, see: (a) Ireland, J. F.; Wyatt, P. A. H. Adv. Phys. Org. Chem. 1976, 12, 131.
3. (b) Klöpffer, W. Adv. Photochem. 1977, 10, 311.
4. (c) Arnaut, L, G.; Formosinho, S, J. J. Photochem. Photobiol A: Chem. 1993, 75, 1.
5. (d) Formosinho, S. J.; Arnaut, L. G. J. Photochem. Photobiol. A: Chem. 1993, 75, 21.
6. (e) Ormson, S. M.; Brown, R. G. Prog. React. Kinet. 1994, 19, 45.
7. (f) Le Gourrierec, D.; Ormson, S. M.; Brown, R. G. Prog. React. Kinet. 1994, 19, 211.
8. (a) Lukeman, M.; Wan, P. Chem. Commun. 2001, 1004.
9. (b) Lukeman, M.; Wan, P. J. Am. Chem. Soc. 2002, 124, 9458.
10. Lukeman, M.; Wan, P. J. Am. Chem. Soc. 2003, 125, 1164,
11. (a) Aoyama, Y.; Endo, K.; Anzai, T.; Yamaguchi, Y.; Sawaki, T.; Kobayashi, K.; Kanehisa, N.; Hashimoto, H.; Kai, Y.; Masuda, H. J. Am. Chem. Soc. 1996, 118, 5562.
12. (b) Aoyama, Y.; Endo, K.; Kobayashi, K.; Masuda, H. Supramol. Chem. 1994, 4, 229-241.
13. (c) Endo, K.; Ezuhara, T.; Koyanagi, M.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 119, 499.
14. (d) Endo, K.; Sawaki, T.; Koyanagi, M.; Kobayashi, K.; Masuda, H.; Aoyama, Y. J. Am. Chem. Soc. 1995, 117, 8341.
15. (e) Kobayashi, K.; Koyanagi, M.; Endo, K.; Masuda, H.; Aoyama, Y. Eur. J. Chem. 1998, 4, 417.
16. (a) Isaks, M.; Yates, K.; Kalanderopoulos, P. J. Am. Chem. Soc. 1984, 106, 2728.
17. (b) Kalanderopoulos, P.; Yates, K. J. Am. Chem. Soc. 1986, 108, 6290.
18. (c) Fischer, M.; Wan, P. J. Am. Chem. Soc. 1998, 120, 2680.
19. (d) Fischer, M.; Wan, P. J. Am. Chem. Soc. 1999, 121, 4555.
20. (e) Brousmiche, D. W.; Xu, M.; Lukeman, M.; Wan, P. J. Am. Chem. Soc. 2003, 125, 12961.
21. Kevill, D. N.; Anderson, S. W. J. Org. Chem. 1991, 56, 1845.
22. Budac, D.; Wan, P. J. Org. Chem. 1992, 57, 887.
23. Melhuish, W. H. J. Phys. Chem. 1960, 64, 762.
24. Berlman, I. B. Handbook of Fluorescence Spectra of Aromatic Molecules; Academic Press: New York, 1971; p 363.
25. Werst, D. W.; Gentry, W. R.; Barbara, P. F. J. Phys. Chem. 1985, 89, 729.
26. Sakata, K.; Hara, K. Chem. Phys. Lett. 2003, 371, 164.
27. Diao, L.; Yang, C.; Wan, P. J. Am. Chem. Soc. 1995, 117, 5369.
28. Carmichael, I.; Helman, W. P.; Hug, G. L. J. Phys. Chem. Ref. Data 1987, 6, 239.
29. Tolbert, L. M.; Solntsev, K. M. Acc. Chem. Res. 2002, 35, 19.
30. Tanner, C.; Mance, C.; Leutwyler, S. Science 2003, 302, 1736.
31. Terao, Y.; Wakui, H.; Nomoto, M.; Satoh, T.; Miura, M.; Nomura, M. J. Org. Chem. 2003, 68, 5236.
32. Rice, J.; Cai, Z.-W. J. Org. Chem. 1993, 58, 1415.