Probing the reactivity of photoinitiators for free radical polymerization: Time-resolved infrared spectroscopic study of benzoyl radicals

Journal of the American Chemical Society

Volumn 124, Issue 50, 2002, Pages 14952-14958

  Colley, Christopher S ^a   Grills, David C ^a   Besley, Nicholas A ^a   Jockusch, Steffen ^b   Matousek, Pavel ^c   Parker, Anthony W ^c   Towrie, Michael ^c   Turro, Nicholas J ^b   Gill, Peter M W ^a   George, Michael W ^a  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

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

^c Harwell Science and Innovation Campus   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

FREE RADICAL POLYMERIZATION; INDICATORS (CHEMICAL); INFRARED SPECTROSCOPY; KETONES; PHOTOLYSIS;

PHOTOINITIATORS;

CHEMICAL ANALYSIS;

FREE RADICAL; KETONE; PHOSPHINE OXIDE DERIVATIVE;

ARTICLE; DIODE LASER; FOURIER TRANSFORMATION; GAS CHROMATOGRAPHY; INFRARED SPECTROSCOPY; KINETICS; MASS SPECTROMETRY; POLYMERIZATION; SPECTROSCOPY; THREE DIMENSIONAL IMAGING;

EID: 0037132610     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja026099m     Document Type: Article

References (36)

1. Crivello, J. V.; Dietliker, K. Photoinitiators for Free Radical Cationic and Anionic Photopolymerization; John Wiley & Sons: Chichester, U.K., 1998; Vol. 3.
2. Dietliker, K. Radiation Curing in Polymer Science and Technology; Elsevier Applied Science: New York, 1993; Vol. 2.
3. Rutsch, W.; Dietliker, K.; Leppard, D.; Kohler, M.; Misev, L.; Kolczak, U.; Rist, G. Prog. Org. Coat. 1996, 27, 227-39.
4. Herz, C. P.; Eichler, J. Farbe Lack 1979, 85, 933.
5. Eichler, J. Herz, C. P.; Naito, I.; Schnabel, W. J. Photochem. 1980, 12, 225-34.
6. Jockusch, S.; Landis, M. S.; Freiermuth, B.; Turro, N. J. Macromolecules 2001, 34, 1619-26.
7. Eichler, J.; Herz, C. P.; Schnabel, W. Angew. Makromol. Chem. 1980, 91, 39-54.
8. Leopold, D.; Fischer, H. J. Chem. Soc., Perkin Trans. 2 1992, 513-17.
9. Rist, G.; Borer, A.; Dietliker, K.; Desobry, V.; Fouassier, J.-P.; Ruhlmann, D. Macromolecules 1992, 25, 4182-93.
10. Ruhlmann, D.; Fouassier, J.-P.; Schnabel, W. Eur. Polym. J. 1992, 28, 287-92.
11. Jockusch, S.; Koptyug, I. V.; McGarry, P. F.; Sluggett, G. W.; Turro, N. J.; Watkins. D. M. J. Am. Chem. Soc. 1997, 119, 11495-501.
12. Kolczak, U.; Rist, G.; Dietliker, K.; Wirz, J. J. Am. Chem. Soc. 1996, 118, 6477-89.
13. Martschke, R.; Farley, R. D.; Fischer, H. Helv. Chim. Acta 1997, 80, 1363-74.
14. Jockusch, S.; Turro, N. J. J. Am. Chem. Soc. 1999, 121, 3921-25.
15. Sluggett, G. W.; McGarry, P. F.; Koptyug, I. V.; Turro, N. J. J. Am. Chem. Soc. 1996, 118, 7367-72.
16. Jockusch, S.; Turro, N. J. J. Am. Chem. Soc. 1998, 120, 11773-77.
17. Huggenberger, C.; Lipscher, J.; Fischer, H. J. Phys. Chem. 1980, 84, 3467-74.
18. Fischer, H.; Baer, R.; Hany, R.; Verhoolen, I.; Walbiner, M. J. Chem. Soc., Perkin Trans. 2 1990, 787-98.
19. Vasenkov, S.; Frei, H. J. Phys. Chem. A 2000, 104, 4327-32.
20. Sluggett, G. W.; Turro, C.; George, M. W.; Koptyug, I. V.; Turro, N. J. J. Am. Chem. Soc. 1995, 117, 5148-53.
21. Brown, C. E.; Neville, A. G.; Rayner, D. M.; Ingold, K. U.; Lusztyk, J. Aust. J. Chem. 1995, 48, 363-79.
22. Neville, A. G.; Brown, C. E.; Rayner, D. M.; Lusztyk, J.; Ingold, K. U. J. Am. Chem. Soc. 1991, 113, 1869-70.
23. George, M. W.; Poliakoff, M.; Turner, J. J. Analyst 1994, 119, 551-60.
24. Sun, X. Z.; Nikiforov, S. M.; Yang, J.; Colley, C. S.; George, M. W. Appl. Spectrosc. 2002, 56, 31-39.
25. Towrie, M.; Bailey, P. D.; Barton, R.; Matousek, P.; Parker, A. W.; George, M. W.; Grills, D. C. Central Laser Facility, Rutherford Appleton Laboratory Annual Report 2000/2001, pp 165-67; see http://www.clf.rl.ac.uk/Report/2000-2001/pdf/75.pdf.
26. Towrie, M.; Grills, D. C.; Dyer, J.; Weinstein, J. A.; Matousek, P.; Barton, R.; Bailey, P. D.; Subramaniam, N.; Kwok, W. M.; Ma, C.; Phillips, D.; Parker, A. W.; George, M. W. Appl. Spectrosc. 2002 (in press).
27. Kong, J.; White, C. A.; Krylov, A. I.; Sherrill, D.; Adamson, R. D.; Furlani, T. R.; Lee, M. S.; Lee, A. M.; Gwaltney, S. R.; Adams, T. R.; Ochsenfeld, C.; Gilbert, A. T. B.; Kedziora, G. S.; Rassolov, V. A.; Maurice, D. R.; Nair, N.; Shao, Y.; Besley, N. A.; Maslen, P. E.; Dombroski, J. P.; Daschel, H.; Zhang, W.; Korambath, P. P.; Baker, J.; Byrd, E. F. C.; Van Voorhis, T.; Oumi, M.; Hirata, S.; Hsu, C.-P.; Ishikawa, N.; Florian, J.; Warshel, A.; Johnson, B. G.; Gill, P. M. W.; Head-Gordon, M.; Pople, J. A. J. Comput. Chem. 2000, 21, 1532-48.
28. Adamson, R. D.; Gill, P. M. W.; Pople, J. A. Chem. Phys. Lett. 1998, 284, 6-11.
29. Besley, N. A.; Colley, C. S.; Yang, J.; George, M. W.; Gill, P. M. W. Manuscript in preparation.
30. 2-FTIR.
31. Sumiyoshi, T.; Schnabel, W.; Henne, A.; Lechtken, P. Polymer 1985, 26, 141-46.
32. Baxter, J. E.; Davidson, R. S.; Hageman, H. J.; McLauchlan, K. A.; Stevens, D. G. J. Chem. Soc., Chem. Commun. 1987, 73-75.
33. 2-FTIR and ps-TRIR experiments, where the UV laser energy is lower than in the diode laser-based TRIR experiment. Observation of 7 is possible with diode laser-based TRIR since there is sufficient UV photon fluence to pump the multiphoton process.
34. acrylate) will be unaffected and are therefore directly comparable. The kinetics of n-butylacrylate addition to 4b were measured in both laboratories, giving identical rate constants.
35. 3 was present. This is consistent with the formation of the rearrangement product 7 during these trapping experiments. The precise mechanism is still unclear and further experiments are in progress to fully understand this process.
36. Fleming, I. Frontier Orbitals and Organic Chemical Reactions; John Wiley & Sons: Chichester, U.K., 1978.