Photophysical properties of intramolecular charge-transfer excited singlet state of aminofluorenone derivatives

Journal of Physical Chemistry A

Volumn 102, Issue 18, 1998, Pages 3018-3024

  Yatsuhashi, Tomoyuki ^a,b   Nakajima, Yuka ^a   Shimada, Tetsuya ^a   Inoue, Haruo ^a  

^a TOKYO METROPOLITAN UNIVERSITY   (Japan)

^b Osaka Prefecture University   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000774889     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp980158u     Document Type: Article

References (57)

1. Bagchi, B. Annu. Rev. Phys. Chem. 1989, 40, 115. Simon, J. D. Pure Appl. Chem. 1990, 62, 2243.
2. Bagchi, B. Annu. Rev. Phys. Chem. 1989, 40, 115. Simon, J. D. Pure Appl. Chem. 1990, 62, 2243.
3. Horng, M. L.; Gardecki, J. A.; Papazyan, A.; Maroncelli, M. J. Phys. Chem. 1995, 99, 17311. Reid, P. J.; Barbara, P. F. J. Phys. Chem. 1995, 99, 3554. Stratt, R. M.; Maroncelli, M. J. Phys. Chem. 1996, 100, 12981.
4. Horng, M. L.; Gardecki, J. A.; Papazyan, A.; Maroncelli, M. J. Phys. Chem. 1995, 99, 17311. Reid, P. J.; Barbara, P. F. J. Phys. Chem. 1995, 99, 3554. Stratt, R. M.; Maroncelli, M. J. Phys. Chem. 1996, 100, 12981.
5. Horng, M. L.; Gardecki, J. A.; Papazyan, A.; Maroncelli, M. J. Phys. Chem. 1995, 99, 17311. Reid, P. J.; Barbara, P. F. J. Phys. Chem. 1995, 99, 3554. Stratt, R. M.; Maroncelli, M. J. Phys. Chem. 1996, 100, 12981.
6. Inoue, H.; Hida, M.; Nakashima, N.; Yoshihara, K. J. Phys. Chem. 1982, 86, 3184.
7. Yatsuhashi, T.; Inoue, H. J. Phys. Chem. A 1997, 101, 8166.
8. (a) Ritter, J.; Borst, H. U.; Lindner, T.; Hauser, M.; Brosig, S.; Bredereck, K.; Steiner, U. E.; Kühn, D.; Kelemen, J.; Kramer., H. E. A. J. Photochem. Photobiol. A 1988, 41, 227. Borst, H. U.; Kelemen, J.; Fabian, J.; Nepras, M.; Kramer, H. E. A. J. Photochem. Photobiol. A 1992, 69, 97.
9. (a) Ritter, J.; Borst, H. U.; Lindner, T.; Hauser, M.; Brosig, S.; Bredereck, K.; Steiner, U. E.; Kühn, D.; Kelemen, J.; Kramer., H. E. A. J. Photochem. Photobiol. A 1988, 41, 227. Borst, H. U.; Kelemen, J.; Fabian, J.; Nepras, M.; Kramer, H. E. A. J. Photochem. Photobiol. A 1992, 69, 97.
10. (b) Srivatsavoy, V. J. P.; Venkataraman, B.; Periasamy, N. J. Photochem. Photobiol. A 1992, 68, 169. Proc. Indian Acad. Sci. Chem. Sci. 1992, 104, 731.
11. (b) Srivatsavoy, V. J. P.; Venkataraman, B.; Periasamy, N. J. Photochem. Photobiol. A 1992, 68, 169. Proc. Indian Acad. Sci. Chem. Sci. 1992, 104, 731.
12. (c) Flom, S. R.; Barbara, P. F. J. Phys. Chem. 1985, 89, 4489.
13. (d) Jones, G., II; Feng, Z.; Bergmark, W. R. J. Phys. Chem. 1994, 98, 4511.
14. (e) Lin, S.; Struve, W. S. J. Phys. Chem. 1991, 95, 2251.
15. (a) Kobayashi, T.; Nagakura, S. Chem. Phys. Lett. 1976, 43, 429. Andrews, L. J.; Deroulede, A.; Linschitz, H. J. Phys. Chem. 1978, 82, 2304. Biczók, L.; Bérces, T. J. Phys. Chem. 1988, 92, 3842. Fujii, T.; Sano, M.; Mishima, S.; Hiratsuka, H. Bull. Chem. Soc. Jpn. 1996, 69, 1833.
16. (a) Kobayashi, T.; Nagakura, S. Chem. Phys. Lett. 1976, 43, 429. Andrews, L. J.; Deroulede, A.; Linschitz, H. J. Phys. Chem. 1978, 82, 2304. Biczók, L.; Bérces, T. J. Phys. Chem. 1988, 92, 3842. Fujii, T.; Sano, M.; Mishima, S.; Hiratsuka, H. Bull. Chem. Soc. Jpn. 1996, 69, 1833.
17. (a) Kobayashi, T.; Nagakura, S. Chem. Phys. Lett. 1976, 43, 429. Andrews, L. J.; Deroulede, A.; Linschitz, H. J. Phys. Chem. 1978, 82, 2304. Biczók, L.; Bérces, T. J. Phys. Chem. 1988, 92, 3842. Fujii, T.; Sano, M.; Mishima, S.; Hiratsuka, H. Bull. Chem. Soc. Jpn. 1996, 69, 1833.
18. (a) Kobayashi, T.; Nagakura, S. Chem. Phys. Lett. 1976, 43, 429. Andrews, L. J.; Deroulede, A.; Linschitz, H. J. Phys. Chem. 1978, 82, 2304. Biczók, L.; Bérces, T. J. Phys. Chem. 1988, 92, 3842. Fujii, T.; Sano, M.; Mishima, S.; Hiratsuka, H. Bull. Chem. Soc. Jpn. 1996, 69, 1833.
19. (b) Kuboyama, A. Bull. Chem. Soc. Jpn. 1964, 37, 1540. Yoshihara, K.; Kearns, D. R. J. Chem. Phys. 1966, 45, 1991. Singer, L. A. Chem. Phys. Lett. 1969, 12, 923.
20. (b) Kuboyama, A. Bull. Chem. Soc. Jpn. 1964, 37, 1540. Yoshihara, K.; Kearns, D. R. J. Chem. Phys. 1966, 45, 1991. Singer, L. A. Chem. Phys. Lett. 1969, 12, 923.
21. (b) Kuboyama, A. Bull. Chem. Soc. Jpn. 1964, 37, 1540. Yoshihara, K.; Kearns, D. R. J. Chem. Phys. 1966, 45, 1991. Singer, L. A. Chem. Phys. Lett. 1969, 12, 923.
22. (c) Biczók, L.; Bérces, T.; Márta, F. J. Phys. Chem. 1993, 97, 8895.
23. Biczók, L.; Berces, T.; Linschitz, H. J. Am. Chem. Soc. 1997, 119, 11071.
24. Moog, R. S.; Burozski, N. A.; Desai, M. M.; Good, W. R.; Silvers, C. D.; Thompson, P. A.; Simon, J. D. J. Phys. Chem. 1991, 95, 8466.
25. Arai, S.; Kato, S.; Hida, M. Bull. Chem. Soc. Jpn. 1985, 58, 1458.
26. Parker, C. A. Photoluminescence of Solutions; Elsevier: Essex, 1968; Chapter 3.
27. Melhuish, W. H. J. Phys. Chem. 1961, 65, 229.
28. Murov, S. L.; Carmichael, I.; Hug, G. L. Handbook of Photochemistry, 2nd ed.; Marcel Dekker: New York, 1993.
29. Riddick, J. A.; Bunger, W. B.; Sakano, T. K. Organic Solvents, 4th ed.; John Wiley & Sons: New York, 1986.
30. -1 (2DMAF), respectively. Other MAFs and DMAFs are shown in Experimental Section.
31. (a) Boykin, D. W.; Nowak-Wyda, B. Magn. Reson. 1991, 29, 152.
32. (b) Baumstark, A. L.; Graham, S. S.; Boykin, D. W. Tetrahedron Lett. 1990, 31, 957.
33. 6 at 30 °C were 6.68 (1AF), 5.62 (2AF), 6.45 (3AF), and 5.69 (4AF), respectively.
34. Inoue, H.; Hoshi, T.; Yoshino, J.; Tanizaki, Y. Bull. Chem. Soc. Jpn. 1972, 45, 1018; 1973, 46, 380. Tachibana, H.; Yatsuhashi, T.; Shimada, T.; Inoue, H., manuscript in preparation.
35. Inoue, H.; Hoshi, T.; Yoshino, J.; Tanizaki, Y. Bull. Chem. Soc. Jpn. 1972, 45, 1018; 1973, 46, 380. Tachibana, H.; Yatsuhashi, T.; Shimada, T.; Inoue, H., manuscript in preparation.
36. Inoue, H.; Hoshi, T.; Yoshino, J.; Tanizaki, Y. Bull. Chem. Soc. Jpn. 1972, 45, 1018; 1973, 46, 380. Tachibana, H.; Yatsuhashi, T.; Shimada, T.; Inoue, H., manuscript in preparation.
37. Mataga, N.; Kaifu, Y.; Koizumi, M. Bull. Chem. Soc. Jpn. 1955, 28, 690. Lippen, E. Z. Naturforsch. 1955, 10, 541.
38. Mataga, N.; Kaifu, Y.; Koizumi, M. Bull. Chem. Soc. Jpn. 1955, 28, 690. Lippen, E. Z. Naturforsch. 1955, 10, 541.
39. 3 (3DMAF). The excited-state dipole moment of 4-aminofluorenone was estimated as 10.6-13 D by Hagan et al.: Hagan, T.; Pilloud, D.; Suppan, P. Chem. Phys. Lett. 1987, 139, 499.
40. 3 (2PAQ).
41. The distance between the carbonyl oxygen and the hydrogen of amino group was calculated as 2.46 Å (1AF) and 1.84 Å (1AAQ) by MOPAC93 (PM3).
42. Srivatsavoy, V. J. P.; Venkataraman, B.; Periasamy, N. J. Photochem. Photobiol. A 1992, 68, 169.
43. Baumstark, A. L.; Dotrong, M.; Stark. R. R.; Boykin, D. W. J. Chem. Soc., Chem. Commun. 1989, 767.
44. Harju, T. O.; Huizer, A. H.; Varma, C. A. G. O. Chem. Phys. 1995, 200, 215.
45. max (nm) in ethanol at 77 K are 455 (shoulder), 490 and 512 (fluorenone); 502 (IAF); 530 (3AF); 555 (4AF); 506 (IMAF); 487 (shoulder) and 526 (3MAF); 564 and 597 (4MAF); 506 (IDMAF); 503 and 532 (3DMAF); 568 (4DMAF). 3-Substituted fluorenones showed weak vibronic structure, and the spectral shapes were very similar to that of fluorenone.
46. Shirota, H.; Pal, H.; Tominaga, K.; Yoshihara, K. J. Phys. Chem. 1996, 100, 14575.
47. Englman, R.; Jortner, J. Mol. Phys. 1970, 18, 145. Fread, K. F.; Jortner, J. J. Chem. Phys. 1970, 52, 6272.
48. Englman, R.; Jortner, J. Mol. Phys. 1970, 18, 145. Fread, K. F.; Jortner, J. J. Chem. Phys. 1970, 52, 6272.
49. 2 (7.82), respectively. Hydroxy-9-fluorenones (HFs) were obtained from Nacarai (2HF, GR reagent), Aldrich (4HF, 98%). 1HF and 3HF were synthesized from the corresponding AFs by diazotization followed by hydrolysis and purified by recrystallization and served only for absorption measurement. Ionization potentials were referred from: Watanabe, K. J. Chem. Phys. 1957, 26, 542. Watanabe, K.; Mottl, J. R. J. Chem. Phys. 1957, 26, 1773.
50. 2 (7.82), respectively. Hydroxy-9-fluorenones (HFs) were obtained from Nacarai (2HF, GR reagent), Aldrich (4HF, 98%). 1HF and 3HF were synthesized from the corresponding AFs by diazotization followed by hydrolysis and purified by recrystallization and served only for absorption measurement. Ionization potentials were referred from: Watanabe, K. J. Chem. Phys. 1957, 26, 542. Watanabe, K.; Mottl, J. R. J. Chem. Phys. 1957, 26, 1773.
51. Yoshida, Z.; Takabayashi, F. Tetrahedron 1967, 24, 933.
52. Matsuura, T. Kagaku Ryouiki 1969, 23, 858.
53. Rotkiewicz, K.; Grellmann, K. H.; Grabowski, Z. R. Chem. Phys. Lett. 1973, 19, 315. Rettig, W. Angew. Chem., Int. Ed. Engl. 1986, 25, 971.
54. Rotkiewicz, K.; Grellmann, K. H.; Grabowski, Z. R. Chem. Phys. Lett. 1973, 19, 315. Rettig, W. Angew. Chem., Int. Ed. Engl. 1986, 25, 971.
55. Jones, G.; Feng, Z.; Bergmark, W. R. J. Phys. Chem. 1994, 98, 4511.
56. Soujanya, T.; Fessenden, R. W.; Samanta, A. J. Phys. Chem. 1996, 100, 3507.
57. Demeter, A.; Berces, T.; Biczók, L.; Wintgens, V.; Valat, P.; Kossanyi, J. J. Phys. Chem. 1996, 100, 2001.