The effect of addition of fluorescent moieties to dihydropyrenes: Enhancing photochromicity and fluorescence monitoring

Journal of Organic Chemistry

Volumn 72, Issue 21, 2007, Pages 7939-7946

  Mitchell, Reginald H ^a   Bohne, Cornelia ^a   Robinson, Stephen G ^a   Yang, Yanhong ^a  

^a UNIVERSITY OF VICTORIA   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

FLUORESCENCE; ISOMERS; QUANTUM YIELD; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

DIHYDROPYRENES; FLUORESCENT MOIETIES; PHOTOCHROMIC CYCLING; RING OPENING QUANTUM YIELDS;

AROMATIC HYDROCARBONS;

DIHYDROPYRIDINE DERIVATIVE; METACYCLOPHANE DERIVATIVE; PYRENE DERIVATIVE;

ADDITION REACTION; ARTICLE; FLUORESCENCE; HALF LIFE TIME; ISOMER; MOLECULAR STABILITY; MONITORING; QUANTUM YIELD; RING OPENING; SYNTHESIS;

EID: 35348836566     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo0712392     Document Type: Article

References (35)

1. Bouas-Laurent, H.; Dürr, H. Organic Photochromism (IUPAC Technical Report). Pure Appl. Chem. 2001, 73, 639-665.
2. Irie, M. (Guest Editor) Chem. Rev. 2000, 100, 1683-1890.
3. Sheepwash, M. A.; Mitchell, R. H.; Bohne, C. J. Am. Chem. Soc. 2002, 124, 4693-4700.
4. Tashiro, M.; Yamato, T. J. Am. Chem. Soc. 1982, 104, 3701-3707.
5. Mitchell, R. H. Eur. J. Org. Chem. 1999, 2695-2703.
6. Mitchell, R. H.; Ward, T. R.; Chen, Y.; Wang, Y.; Weerawarna, S. A.; Dibble, P. W.; Marsella, M. J.; Almutairi, A.; Wang, Z. Q. J. Am. Chem. Soc. 2003, 125, 2974-2988.
7. Murakami, S.; Tsutsui, T.; Saito, S.; Yamato, T.; Tashiro, M. Nippon Kaguku Kaishi 1988, 2, 221-229; Chem. Abs. 1989, 110, 23163.
8. Blattman, H. R.; Schmidt, W. Tetrahedron 1970, 26, 5885-5899.
9. Phillips, J. B.; Molyneux, R. J.; Sturm, E.; Boekelheide, V. J. Am. Chem. Soc. 1967, 89, 1704-1709.
10. (a) Matsuda, K.; Irie, M. J. Photochem. Photobiol. C 2004, 5, 169-182 and references therein.
11. (b) Raymo, F. M.; Tomasulo, M. Chem. Soc. Rev. 2005, 34, 327-336 and references therein.
12. (c) Raymo, F. M.; Tomasulo, M. J. Phys. Chem. A 2005, 109, 7343-7352 and references therein.
13. (d) de Meijere, A.; Zhao, L.; Belov, V.; Bossi, M.; Noltemeyer, M.; Hell, S. W. Chem. - Eur. J. 2007, 13, 2503-2526.
14. (e) Fukaminato, T.; Sasaki, T.; Kawai, T.; Tamai, N.; Irie, M. J. Am. Chem. Soc. 2004, 126, 14843-14849.
15. (f) Fukaminato, T.; Umemoto, T.; Iwata, Y.; Yokojima, S.; Yoneyama, M.; Nakamura, S.; Irie, M. J. Am. Chem. Soc. 2007, 129, 5932-5938.
16. Sheepwash, M. A.; Ward, T. R.; Wang, Y.; Bandyopadhyay, S.; Mitchell, R. H.; Bohne, C. Photochem. Photobiol. Sci. 2003, 2, 104-122.
17. (a) Boekelheide, V.; Sturm, E. J. Am. Chem. Soc. 1969, 91, 902-908.
18. (b) Boekelheide, V.; Hylton, T. A. J. Am. Chem. Soc. 1970, 92, 3669-3675.
19. (a) Andes Hess, B.; Bailey, A. S.; Bartusek, B.; Boekelheide, V. J. Am. Chem. Soc. 1969, 91, 1665-1671.
20. (b) Andes Hess, B.; Boekelheide, V. J. Am. Chem. Soc. 1969, 91, 1672-1678.
21. See: Dixon, K. R.; Mitchell, R. H. Can. J. Chem. 1983, 61, 1598-1602 and the references therein.
22. (a) Tashiro, M.; Yamato, T. Org. Prep. Proc. Int. 1982, 14, 216-219.
23. (b) Miyazawa, A.; Yamato, T.; Tashiro, M. J. Org. Chem. 1991, 56, 1334-1337.
24. 1/2 (46°C) values are then 3.12 h (Ayub) and 3.11 h (ref 7).
25. Williams, R. V.; Edwards, W. D.; Mitchell, R. H.; Robinson, S. G. J. Am. Chem. Soc. 2005, 127, 16207-16214.
26. (a) Wilkinson, F.; Worrall, D. R.; Hobley, J.; Jansen, L.; Willimas, S. L.; Langley, A. J.; Matousek, P. J. Chem. Soc., Faraday Trans. 1996, 92, 1331-1336.
27. (b) Tamai, N.; Masuhara, H. Chem. Phys. Lett. 1992, 191, 189-194.
28. (c) Martin, S. C.; Singh, N.; Wallace, S. C. J. Phys. Chem. 1996, 100, 8066-8069.
29. (d) Kurita, S.; Kashiwaga, A.; Kurita, Y.; Miyasaki, H.; Mataga, N. Chem. Phys. Lett. 1990, 171, 553-557.
30. (e) Tamai, N.; Saika, T.; Shimidzu, T.; Irie, M. J. Phys. Chem. 1996, 100, 4689-4692.
31. (f) Miyasaka, H.; Araki, S.; Tabata, A.; Nobuto, T.; Mataga, N.; Irie, M. Chem. Phys. Lett. 1994, 230, 249-254. .
32. Boggio-Pasqua, M.; Bearpark, M. J.; Robb, M. A. J. Org. Chem. 2007, 72, 4497-4503.
33. Murov, S. L.; Carmichael, I.; Hug, G. L. Handbook of Photochemistry, 2nd revised and expanded ed.; Marcel Dekker, Inc.: New York, 1993.
34. (a) Hatchard, C. G.; Parker, C. A. Proc. R. Soc. London, Ser. A 1956, 518-536.
35. (b) Parker, C. A. Proc. R. Soc. London, Ser. A 1953, 220, 104.