Energetics of electron-transfer reactions of photoinitiated polymerization: Dye-sensitized fragmentation of N-alkoxypyridinium salts

Helvetica Chimica Acta

Volumn 84, Issue 9, 2001, Pages 2796-2812

  Gould, Ian R ^a   Shukla, Deepak ^b   Giesen, David ^b   Farid, Samir ^b  

^a ARIZONA STATE UNIVERSITY   (United States)

^b EASTMAN KODAK COMPANY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ABSORPTION; CHEMICAL BONDS; DYES; FREE RADICAL POLYMERIZATION; FREE RADICALS; MONOMERS; PHOTODISSOCIATION; PROBABILITY DENSITY FUNCTION;

ELECTRON-TRANSFER REACTIONS;

PHOTOPOLYMERIZATION;

ACRYLIC ACID; DYE; PYRIDINE DERIVATIVE; PYRIDINIUM DERIVATIVE;

ABSORPTION; ARTICLE; CALCULATION; DISSOCIATION; ELECTRON TRANSPORT; ENERGY TRANSFER; POLYMERIZATION; QUANTUM THEORY;

EID: 0034753571     PISSN: 0018019X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1522-2675(20010919)84:9<2796::AID-HLCA2796>3.0.CO;2-G     Document Type: Article

References (38)

1. a) A. Reiser, 'Photoreactive Polymers, the Science and Technology of Resists', Wiley, New York, 1989;
2. b) S. P. Pappas, 'UV Curing: Science and Technology', Technology Marketing Publication, Stamford, 1978, and references therein.
3. a) D. P. Specht, C. G. Houle, S. Y. Farid, U.S. Patent 4,289,844, 1981;
4. b) J. L. R. Williams, D. P. Specht, S. Farid, Polym. Eng. Sci. 1983, 23, 1022.
5. J. Paczkowski, D. C. Neckers, in 'Electron Transfer in Chemistry, Vol. 5', Ed. V. Balzani, Wiley-VCH, New York, 2001, p. 516.
6. a) J. V. Crivello, Adv. Polym. Sci. 1984, 62, 1;
7. b) F. D. Saeva, Adv. Electron Transfer Chem. 1994, 4, 1;
8. c) R. J. DeVoe, P. M. Olofson, M. R. V. Sahyun, Adv. Photochem. 1992, 17, 313;
9. d) F. D. Saeva, Top. Curr. Chem. 1990, 156, 59.
10. G. B. Schuster, Adv. Electron Transfer Chem. 1991, 1, 163.
11. S. Y. Farid, N. F. Haley, R. E. Moody, D. P. Specht, U.S. Patents 4,743,528, 4,743,529, 4,743,530, and 4,743,531, 1988.
12. a) W. Schnabel, Macromol. Rapid Commun. 2000, 21, 628;
13. b) Q. Q. Zhu, W. Schnabel, Eur. Polym. J. 1997, 3, 1325;
14. c) Y. Yagci, W. Schnabel, Macromol. Symp. 1994, 85, 115;
15. d) N. Kayaman, A. Onen, Y. Yagci, W. Schnabel, Polym. Bull. 1994, 32, 589.
16. a) K. Y. Lee, J. K. Kochi, J. Chem. Soc., Perkin Trans. 2 1992, 7, 1011;
17. b) J. O. Howell, J. M. Goncalves, C. Amatore, L. Klasinc, R. M. Wightman, J. K. Kochi, J. Am. Chem. Soc. 1984, 106, 3968.
18. I. R. Gould, E. Lorance, unpublished results.
19. R. S. Nicholson, I. Shain, Anal. Chem. 1964, 36, 706.
20. a) R. Popielarz, D. R. Arnold, J. Am. Chem. Soc. 1990, 112, 3068;
21. b) P. Maslak, T. M. Vallombroso, W. H. Chapman Jr., J. N. Narvaez, Angew. Chem., Int. Ed. 1994, 33, 73.
22. A. D. Becke, J. Chem. Phys. 1993, 98, 5648.
23. a) W. J. Hehre, R. Ditchfield, J. A. Pople, J. Chem. Phys. 1972, 56, 2257;
24. b) R. Krishnan, J. S. Binkley, R. Seeger, J. A. Pople, J. Chem. Phys. 1980, 72, 650;
25. c) A. D. McLean, G. S. Chandler, J. Chem. Phys. 1980, 72, 5639.
26. Gaussian98 Revision A7: M. J. Frisch, G. W. Trucks, H. B. Schlegel, G. E. Scuseria, M. A. Robb, J. R. Cheeseman, V. G. Zakrzewski, J. A. Montgomery, R. E. Stratmann, J. C. Burant, S. Dapprich, J. M. Millam, A. D. Daniels, K. N. Kudin, M. C. Strain, O. Farkas, J. Tomasi, V. Barone, M. Cossi, R. Cammi, B. Mennucci, C. Pomelli, C. Adamo, S. Clifford, J. Ochterski, G. A. Petersson, P. Y. Ayala, Q. Cui, K. Morokuma, D. K. Malick, A. D. Rabuck, K. Raghavachari, J. B. Foresman, J. Cioslowski, J. V. Ortiz, B. B. Stefanov, G. Liu, A. Liashenko, P. Piskorz, I. Komaromi, R. Gomperts, R. L. Martin, D. J. Fox, T. Keith, M. A. Al-Laham, C. Y. Peng, A. Nanayakkara, C. Gonzalez, M. Challacombe, P. M. W. Gill, B. Johnson, W. Chen, M. W. Wong, J. L. Andres, C. Gonzalez, M. Head-Gordon, E. S. Replogle, J. A. Pople, Gaussian, Inc., Pittsburgh, USA, 1998.
27. D. J. Giesen, G. D. Hawkins, D. A. Liotard, C. J. Cramer, D. G. Truhlar, Theor. Chem. Acc. 1997, 98, 85.
28. AMSOL 6.5.1, G. D. Hawkins, D. J. Giesen, G. C. Lynch, C. C. Chambers, J. Rossi, J. W. Storer, J. Li, D. Rinaldi, D. A. Liotard, C. J. Cramer, D. G. Truhlar, University of Minnesota, Minneapolis, USA, 1998.
29. A. P. Scott, L. Radom, J. Phys. Chem. 1996, 100, 16502.
30. A. Weller, Z. Phys. Chem. (Munich) 1982, 130, 129.
31. B. R. Arnold, S. Farid, J. L. Goodman, I. R. Gould, J. Am. Chem. Soc. 1996, 118, 5482.
32. a) J. R. Lenhard, J. Imaging Sci. 1986, 30, 27;
33. b) J. R. Lenhard, A. D. Cameron, J. Phys. Chem. 1993, 97, 4916;
34. c) R. O. Loutfy, J. H. Sharp, Photogr. Sci. Eng. 1976, 20, 165.
35. N. J. Turro, 'Modern Molecular Photochemistry', Benjamin/Cummings, Menlo Park, 1978.
36. I. R. Gould, S. Farid, Acc. Chem. Res. 1996, 29, 522.
37. D. P. Specht, P. A. Martic, S. Farid, Tetrahedron 1982, 38, 1203.
38. S. Y. Farid, R. E. Moody, U.S. Patent 4,859,572, 1989.