Twisted intramolecular charge transfer states in 2-arylbenzotriazoles: Fluorescence deactivation via intramolecular electron transfer rather than proton transfer

Journal of Physical Chemistry A

Volumn 106, Issue 34, 2002, Pages 7680-7689

  Maliakal, Ashok ^a   Lem, George ^a   Turro, Nicholas J ^a   Ravichandran, Ravi ^b   Suhadolnik, Joseph C ^b   DeBellis, Anthony D ^b   Wood, Mervin G ^b   Lau, Jacqueline ^b  

^a Och Spine at New York Presbyterian Hospitals   (United States)

^b CIBA GEIGY LTD   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

CHARGE TRANSFER; DIFFUSION; DYE LASERS; FLUORESCENCE; GROUND STATE; HYDROGEN BONDS; QUANTUM THEORY; QUENCHING;

EXCITED STATE INTRAMOLECULAR PROTON TRANSFER (ESIPT); ULTRAVIOLET ABSORBERS (UVA);

AROMATIC COMPOUNDS;

EID: 0037194986     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp021000j     Document Type: Article

References (49)

1. Otterstedt, J. J. Chem. Phys. 1973, 58, 5716.
2. Decker, C.; Biry, S.; Zahouily, K. Polym. Degrad. Stab. 1995, 42, 111.
3. Catalan, J.; Valle, J.D.; Fabero, F.; Garcia, N. Photochem. Photobiol. 1995, 61, 118.
4. Weichmann, M.; Port, H.; Frey, W.; Larmer, F.; Elsaesser, T. J. Phys. Chem. 1991, 95, 1918.
5. Goeller, G.; Rieker, J.; Maier, A.; Stezowski, J.; Daltrozzo, E.; Neureiter, M.; Port, H.; Wiechmann, M.; Kramer, H. J. Phys. Chem. 1988, 92, 1452.
6. Kummrow, A.; Dreyer, J.; Chudoba, C.; Stenger, J.; Nibbering, E.T.J.; Elsaesser, T. J. Chin. Chem. Soc. (Taipei) 2000, 47, 721.
7. Weichmann, M.; Port, H. J. Lumin. 1991, 48, 49, 217.
8. Estevez, C.; Bach, R.; Hass, K.; Schneider, W. J. Am. Chem. Soc. 1997, 119, 5445.
9. Flom, S.; Barbara, P. Chem. Phys. Lett. 1983, 94, 488.
10. Ghiggino, K.; Scully, A.; Leaver, I. J. Phys. Chem. 1986, 90, 5089.
11. Rieker, J.; Lemmert-Schmitt, E.; Goeller, G.; Roessler, M.; Stueber, G.; Schettler, H.; Kramer, H.; Stezowski, J.; Hoier, H.; Henkel, H.; Schmidt, A.; Port, H.; Weichmann, M.; Rody, J.; Rytz, G.; Slongo, M.; Birbaum, J. J. Phys. Chem. 1992, 96, 10225.
12. Woessner, G.; Goeller, G.; Rieker, J.; Hoier, H.; Stezowski, J.; Daltrozzo, E.; Neureiter, M.; Kramer, H. J. Phys. Chem. 1985, 89, 3629.
13. Frey, W.; Elsaesser, T. Chem. Phys. Lett. 1992, 189, 565.
14. Dux, R.; Ghiggino, K.; Vogl, O. Aust. J. Chem. 1994, 47, 1461.
15. O'Connor, D.; Scott, G.; Coulter, D.; Gupta, A.; Webb, S.; Yeh, S.; Clark, J. Chem. Phys. Lett. 1985, 121, 417.
16. Scully, A.; Bigger, S.; Ghiggino, K.; Vogl, O. J. Photochem. Photobiol. A 1991, 55, 387.
17. Weichmann, M.; Port, H.; Laermer, F.; Frey, W.; Elsaesser, T. Chem. Phys. Lett. 1990, 165, 28.
18. Woessner, G.; Goeller, G.; Kollat, P.; Stezowski, J.; Hauser, M.; Klein, U.; Kramer, H. J. Phys. Chem. 1984, 88, 5544.
19. DeBellis, A.; Iyengar, R.; Kaprinidis, N.; Rodebaugh, R.; Suhadolnik, J. "Proceedings of Service Life Methodologies and Metrologies Symposium"; Service Life Methodologies and Metrologies Symposium, 1999, Monterey, CA.
20. McGarry, P.F.; Jockusch, S.; Fujiwara, Y.; Kaprinidis, N.A.; Turro, N.J. Phys. Chem. A. 1997, 101, 764.
21. Dai, G.; Wu, S.; Sustic, A.; Vogl, O. Polym. Bull. 1988, 20, 67.
22. Rettig, W. Top. Curr. Chem. 1994, 169, 254 and references therein.
23. Grabowski, Z.; Dobkowski, J. Pure Appl. Chem. 1983, 55, 245.
24. Vogel, M.; Rettig, W. Ber. Bunsen-Ges. Phys. Chem. 1985, 89, 962.
25. Rettig, W. Appl. Phys. B 1988, 45, 145.
26. Elbe, F.; Keck, J.; Fluegge, A.; Kramer, H.; Fischer, P.; Hayoz, P.; Leppard, D.; Rytz, G.; Kaim, W.; Ketterle, M. J. Phys. Chem. A 2000, 104, 8296.
27. Keck, J.; Roessler, M.; Schroeder, C.; Stueber, G.J.; Waiblinger, F.; Stein, M.; LeGoumiérec, D.; Kramer, H.E.A.; Hoier, H.; Hénkel, S.; Fischer, P.; Port, H.; Hirsch, T.; Rytz, G.; Hayoz, P. J. Phys. Chem. B 1998, 102, 6975.
28. Jovanovic, S.; Tosic, M.; Simic, M. J. Phys. Chem. 1991, 95, 10824.
29. Kamiya, M.; Akahori, Y. Bull. Chem. Soc. Jpn. 1970, 43, 268.
30. Schuddeboom, W.; Jonker, S.A.; Warman, J.M.; Leinhos, U.; Kuehnle, W.; Zachariasse, K.A. J. Phys. Chem. 1992, 96, 10809.
31. Suhadolnik, J.; DeBellis, A.; Hendricks-Guy, C.; Iyengar, R.; Wood, M. "Unexpected Electronic Effects on benzotriazole UV absorber photo-stability: Mechanistic Implications beyond excited state intramolecular proton transfer"; ACS National Meeting, 2000, Washington, DC.
32. Bernardi, F.; Olivucci, M.; Robb, M. Chem. Soc. Rev. 1996, 25, 321.
33. Solntsev, K.; Huppert, D.; Agmon, N. J. Phys. Chem. A 1999, 103, 6984.
34. Acuna, A.; Oton, J. J. Lumin. 1979, 20, 379.
35. Dobkowski, J.; Herbich, J.; Galievsky, V.; Thummel, R.; Wu, F.; Waluk, J. Ber. Bunsen-Ges. Phys. Chem. 1998, 102, 469.
36. Nau, W.; Greiner, G.; Rau, H.; Olivucci, M.; Robb, M. Ber. Bunsen-Ges. Phys. Chem. 1998, 102, 486.
37. Shizuka, H. Acc. Chem. Res. 1985, 18, 141.
38. Werner, T. J. Phys. Chem. 1979, 83, 320.
39. Woessner, G. Photophysikalische und photochemische Desaktivierungsprozesse der UV-Stabilisatoren des Benzotriazol-Typs. Doctoral thesis, University of Stuttgart, 1983.
40. Kosower, E. J. Am. Chem. Soc. 1957, 80, 3253.
41. Kosower, E. J. Am. Chem. Soc. 1957, 80, 3261.
42. Stueber, G.; Kieninger, M.; Schettler, H.; Busch, W.; Goeller, B.; Franke, J.; Kramer, H.; Hoier, H.; Henkel, S.; Fischer, P.; Port, H.; Hirsch, T.; Rytz, G.; Birbaum, J. J. Phys. Chem. 1995, 99, 10097.
43. Liptay, W. Angew. Chem., Int. Ed. 1969, 8, 177.
44. Onsager, L. J. Am. Chem. Soc. 1936, 99, 1486.
45. Rettig, W.; Braun, D.; Suppan, P.; Vauthey, E.; Rotkiewicz, K.; Luboradzki, R.; Suwinska, K. J. Phys. Chem. 1993, 97, 13500.
46. Michl, J. J. Mol. Photochem. 1972, 4, 243.
47. Sinicropi, A.; Pischel, U.; Basosi, R.; Nau, W.; Olivucci, M. Angew. Chem., Int. Ed. 2000, 39, 4582.
48. Nau, W.; Greiner, G.; Wall, J.; Rau, H.; Olivucci, M.; Robb, M. Angew. Chem., Int. Ed. 1998, 37, 98.
49. Compound 6 (OD >2 absorbance units) was irradiated at 300 nm. The loss rate measured in neat acetonitrile was >0.7 absorbance units/ hour. In 3:1 acetonitrile/DMSO the loss rate drops to 0.16 absorbance units/ hour. Tinuvin P, under identical conditions, showed a loss rate of 0.08 absorbance units/hour in acetonitrile, and >0.7 abs. units/hour in 3:1 acetonitrile/DMSO.