DMSO solvent induced photochemistry in highly photostable compounds. The role of intermolecular hydrogen bonding

Journal of Physical Chemistry A

Volumn 101, Issue 5, 1997, Pages 764-767

  McGarry, Peter F ^a   Jockusch, Steffen ^a   Fujiwara, Yoshihisa ^a   Kaprinidis, Nikolas A ^a   Turro, Nicholas J ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

ACIDS; EXCIMER LASERS; HYDROGEN BONDS; IONS; LIGHT ABSORPTION; MOLECULAR STRUCTURE; ORGANIC COMPOUNDS; OXYGEN; QUENCHING; SOLUTIONS; SOLVENTS; SPECTRUM ANALYSIS;

EXCIMER LASER EXCITATION; HYDROXYBENZOPHENONE; HYDROXYL FUNCTION; HYDROXYMETHYLPHENYL BENZOTRIAZOLE; PHOTOSTABILITY; TINUVIN P;

PHOTOCHEMICAL REACTIONS;

EID: 0030835189     PISSN: 10895639     EISSN: None     Source Type: Journal    
DOI: 10.1021/jp961382r     Document Type: Article

References (38)

1. Dexter, M. In Encyclopedia of Polymers Science and Technology; Interscience: New York, 1980; Vol. 23; pp 615.
2. Rabek, J. F. Photostabilisation of Polymers - Principles and Applications; Elsevier Applied Science: Barking, U.K., 1990.
3. Heller, H. J.; Blattmann, H. R. Pure Appl. Chem. 1973, 36, 141.
4. Otterstedt, J. E. A. J. Chem. Phys. 1973, 58, 5716.
5. Pickett, J. E.; Moore, J. E. in Sixteenth Annual International Conference on Advances in the Stabilization and Degradation of Polymers, Luzern, Switzerland, 1994; pp 253-269.
6. Pickett, J. E.; Moore, J. E. Polym. Prepr. 1993, 34, 153.
7. Dearth, M. A.; Korniski, T. J.; Gerlock, J. L. Polym. Degrad. Stab. 1995, 48, 111.
8. Gerlock, J. L.; Tang, W.; Dearth, M. A.; Korniski, T. J. Polym. Degrad. Stab. 1995, 48, 121.
9. Pickett, J. E.; Moore, J. E. Polym. Degrad. Stab. 1993, 42, 231.
10. Decker, C.; Zahouily, K. Polym. Mater. Sci. Eng. 1993, 68, 70.
11. Hodgeman, D. K. C. J. Polym. Sci. 1978, 16, 161.
12. Hodgeman, D. K. C. J. Macromol. Sci., Chem. 1980, A14, 173.
13. Kurumada, T.; Ohsawa, H.; Yamazaki, T. Polym. Degrad. Stab. 1987, 19, 263.
14. Gugumus, F. Polym. Degrad. Stab. 1993, 39, 117.
15. Reiker, J.; Lemmert-Schmitt, E.; Goeller, G.; Roessler, M.; Steuber, G. J.; Schettler, H.; Kramer, H. E. A.; Stezowski, J. J.; Hoier, H.; Henkel, S.; Schmidt, A.; Port, H.; Weichmann, M.; Rody, J.; Rytz, G.; Slongo, M.; Birbaum, J.-L. J. Phys. Chem. 1992, 96, 10225.
16. 4. Thus the first band must arise from 1 having an intermolecular hydrogen bond to DMSO. Similar results are obtained for 2.
17. Woessner, G.; Goeller, G.; Rieker, J.; Hoier, H.; Stezowski, J. J.; Daltrozzo, E.; Neureiter, M.; Kramer, H. E. A. J. Phys. Chem. 1985, 89, 3629.
18. Catalán, J.; Pérez, P.; Fabero, F.; Wilshire, J. F. K.; Claramunt, R. M.; Elguero, J. J. Am. Chem. Soc. 1992, 114, 964.
19. Wiechmann, M.; Port, H.; Frey, W.; Lärmer, F.; Elsässer, T. J. Phys. Chem. 1991, 95, 1918.
20. Ghiggino, K. P.; Scully, A. D.; Leaver, I. H. J. Phys. Chem. 1986, 90, 5089.
21. (a) Catalán, J.; Fabero, F.; Guijarro, M. S.; Claramunt, R. M.; Maria, M. D. S.; Foces-Foces, M. C.; Cano, F. H.; Elguero, J.; Sastre, R. J. Am. Chem. Soc. 1990, 112, 747.
22. (b) De Bellis, A. D.; Rodebaugh, R. K.; Suhadolnik, J.; Hendricks-Guy, C. J. Phys. Org. Chem. 1997, 10, in press.
23. Huston, A. L.; Scott, G. W. J. Phys. Chem. 1987, 91, 1408.
24. The intramolecular hydrogen bond has been thoroughly characterized via NMR and FT-IR and will be the subject of an upcoming paper.
25. Dux, R.; Ghiggino, K. P.; Vogl, O. Aust. J. Chem. 1994, 47, 1461.
26. On the basis of the extinction coefficients of the phenolate ions and benzophenone triplet based transient absorption actinometry, an upper limit estimate of photoionization yield is 1/25 of that formed by compound 1. Further work detailing the actinometry experiments and others will be reported elsewhere.
27. McGarry, P. F.; Cheh, J.; Ruiz-Silva, B.; Hu, S.; Wang, J.; Nakanishi, K.; Turro, N. J. J. Phys. Chem. 1996, 100, 646.
28. Werner, T. J. Phys. Chem. 1979, 83, 320.
29. This mechanism is supported by the fact that the observed decay rate constant of the phenolate ion increases with increasing laser intensity in oxygen-saturated solutions. The observed decay rate constants of the phenolate ions should depend on the concentration of singlet oxygen, and the singlet oxygen concentration produced by sensibilization with triplets of 1 depends on the laser intensity.
30. Catalán, J.; Valle, J. C. D.; Fabero, F.; Garcia, N. A. Photochem. Photobiol. 1995, 61, 118.
31. Klöpffer, W. Adv. Photochem. 1977, 10, 350.
32. Bartok, W.; Lucchesi, P. J.; Snider, N. S. J. Am. Chem. Soc. 1962, 84, 1842.
33. McGarry, P. F.; Doubleday, J. C. E.; Wu, C.-H.; Staab, H. A.; Turro, N. J. J. Photochem. Pholobiol., A 1994, 77, 109.
34. Porter, G.; Suppan, P. Trans. Faraday Soc. 1965, 61, 1664.
35. Hou, S.-Y.; Hetherington, W. M., III; Korenowski, G. M.; Eisenthal, K. B. Chem. Phys. Lett. 1979, 68, 282.
36. Unpublished results.
37. Mosquera, M.; Penedo, J. C.; Rodriguez, M. C. R.; Rodriguez-Prieto, F. J. Phys. Chem. 1996, 100, 5398.
38. The lifetime of the ion, while quite long, is short enough to make the encounter between it and a radical species in solution unlikely.