Mechanisms of Photodegradation of Poly(3-alkylthiophenes) in Solution

Macromolecules

Volumn 26, Issue 11, 1993, Pages 2954-2962

  Abdou, Mohamed S A ^a   Holdcroft, Steven ^a  

^a SIMON FRASER UNIVERSITY   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

DEGRADATION; PHOTOCHEMICAL REACTIONS; SOLUTIONS; ULTRAVIOLET RADIATION;

GRIGNARD ROUTE; OXIDATIVE COUPLING; PHOTODEGRADATION; POLYALKYLTHIOPHENE;

POLYMERS;

EID: 0027593747     PISSN: 00249297     EISSN: 15205835     Source Type: Journal    
DOI: 10.1021/ma00063a047     Document Type: Article

References (92)

1. Koezuka, H.; Tsumura, A.; Ando, T. Synth. Met. 1987, 18, 699.
2. Yoshino, K.; Keneto, K.; Takeda, S. Synth. Met. 1987, 18, 741.
3. Burroughes, J. H.; Jones, A. C.; Friend, R. H. Synth. Met. 1989, 28, C735.
4. Assadi, A.; Svensson, C.; Willander, M.; Inganas, O. Appl. Phys. Lett. 1989, 53, 195.
5. Abdou, M. S. A.; Xie, Z. W.; Leung, A.; Holdcroft, S. Synth. Met. 1992, 52, 159.
6. Abdou, M. S. A.; Xie, Z. W.; Lu, X.; Deen, J.; Holdcroft, S. Can. J. Phys., in press.
7. Patil, A. O.; Heeger, A. J.; Wudl, F. Chem. Rev. 1988, 88, 183.
8. Prasad, P. Nonlinear Optical Properties of Polymers; Heeger, A. J., Orenstein, J., Ulrich, D., Eds.; MRS Symposium Proceedings; Materials Research Society: Pittsburgh, PA, 1988; Vol. 109, p 271.
9. Reynolds, J. R. J. Mol. Electron. 1986, 2, 1.
10. Baker, L. B. Electronic and Photonic Applications of Polymers; Bowden, M. J., Turner, R. S., Eds.; Advances in Chemistry Series 218; American Chemical Society: Washington, DC, 1988.
11. Burroughes, J. H.; Bradley, D. D. C.; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend, R. H.; Burns, P. L.; Holmes, A. B. Nature 1990, 347, 539
12. Binh, N. T.; Gailberger, M.; Bassler, H. Synth. Met. 1992, 47, 77.
13. Moses, D. Appl. Phys. Lett. 1992, 60, 3215.
14. Zinger, B.; Mann, K. R.; Hill, M. G.; Miller, L. L. Chem. Mater. 1992, 4, 1113.
15. Evans, C.; Scaiano, J. C. J. Am. Chem. Soc. 1990, 112, 2694.
16. Hattori, T.; Hayes, W.; Wong, K.; Kaneto, K.; Yoshino, K. J. Phys. C: Solid State Phys. 1984, 17, L803.
17. Rughooputh, S. D. V.; Nowak, M.; Hotta, S.; Heeger, A. J.; Wudl, F. Synth. Met. 1987, 21, 41.
18. Linton, J. R.; Frank, C. W.; Rughooputh, S. D. V. Synth. Met. 1989, 28, C393.
19. Ruhe, J.; Colaneri, N. F.; Bradley, D. D. C.; Friend, R. H.; Wegner, G. J. Phys.: Condens. Matter 1990, 2, 5465.
20. Holdcroft, S. Macromolecules 1991, 24, 2119.
21. Holdcroft, S. Macromolecules 1991, 24, 4834.
22. Abdou, M. S. A.; Arroyo, M. I.; Diaz-Quijada, G.; Holdcroft, S. Chem. Mater. 1991, 3, 1003.
23. Clemonson, P. I.; Feast, W. J.; Ahmad, M. M.; Allen, P. C.; Bott, D. C.; Brown, C. S.; Connors, L. M. Polymer, in press.
24. Tsuchihara, K.; Masuda, T.; Hagishimura, T. J. Polym. Sci., Polym. Chem. Ed. 1991, 29, 471.
25. Holdcroft, S. J. Polym. Sci., Polym. Phys. Ed. 1991, 29, 1585.
26. Tamao, K.; Kodama, S.; Nakajima, J.; Kumada, M. Tetrahedron 1982, 38, 3347.
27. Sugimoto, R.; Takeda, S.; Gu, H. B.; Yoshino, K. Chem. Express 1986, 1, 635.
28. Barker, J. M.; Huddleston, P. R.; Wood, M. L. Synth. Commun. 1975, 5, 59.
29. Mao, H.; Xu, B.; Holdcroft, S. Macromolecules, 1993, 26, 1163.
30. Tung, L. H.; Moore, J. C. Fractionation of Synthetic Polymers; Tung, L. H., Ed.; Marcel Dekker Inc.: New York, 1977.
31. Richardson, R. J.; Wiswall, C. E.; Carr, P. A. G.; Hovis, F. E.; Lilenfeld, H. V. J. Appl. Phys. 1981, 52, 4962.
32. Seliger, H. H. J. Chem. Phys. 1964, 40, 3133.
33. Foote, C. S.; Wexler, S.; Ando, W.; Higgins, R. J. Am. Chem. Soc. 1968, 90, 975.
34. Quarmby, C.; Grimshaw, H. M. Analyst 1967, 92, 305.
35. Hotta, S.; Rughooputh, D. D. V.; Heeger, A. J.; Wudl, F. Macromolecules 1987, 20, 212.
36. Schulte, K. E.; Kreutzberger, A.; Bohn, G. Chem. Ber. 1964, 97, 3263.
37. Zerbi, G.; Chierichetti, B.; Inganas, O. J. Chem. Phys. 1991, 94, 4637.
38. Zerbi, G.; Chierichetti, B.; Inganas, O. J. J. Chem. Phys. 1991, 94, 4646.
39. Akimoto, M.; Furukawa, Y.; Takeuchi, H.; Harada, I.; Soma, Y.; Soma, M. Synth. Met. 1986, 25, 353.
40. Furukawa, Y.; Akimoto, M.; Harada, I. Synth. Met. 1987, 18, 151.
41. Hotta, S.; Shimotsuma, W.; Taketani, M. Synth. Met. 1984, 10, 85.
42. 2; Frimer, A. A., Ed.; CRC Press Inc.: Boca Raton, FL, 1985.
43. Bellamy, L. Advances in Infrared Group Frequencies; Bellamy, L., Ed.; Methuen & Co. Ltd.: London, U.K., 1968.
44. Zwanenburg, B.; Strating, J. Quart. Rep. Sulfur Chem. 1970, 5, 79.
45. Detoni, S.; Hadzi, D. J. Chem. Soc. 1955, 3163.
46. Price, C. C.; Gillis, R. J. J. Am. Chem. Soc. 1953, 75, 4750.
47. King, J. F.; Durst, T. Can. J. Chem. 1966, 44, 819.
48. Cymerman, J.; Willis, J. B. J. Chem. Soc. 1951, 1332.
49. Zwanburg, B.; Thijs, L.; Strating, J. Recl. Trav. Chim. Pays-Bas 1967, 86, 577.
50. Sato, M.; Morii, H. Macromolecules 1991, 24, 1196.
51. Sato, M.; Shimizu, T.; Yamauchi, A. Synth. Met. 1991, 41–43, 551.
52. Stein, P. C.; Bolognesi, A.; Catellani, M.; Zetta, L. Synth. Met. 1991, 41–43, 559.
53. Swern, D.; Clements, A. H.; Lung, T. M. Anal. Chem. 1969, 41, 412.
54. Ward, G. A.; Mair, R. D. Anal. Chem. 1969, 41, 538.
55. McLachlan, D.; Arnason, T.; Lam, J. Photochem. Photobiol. 1984, 39, 177.
56. Evans, C.; Weir, D.; Scaiano, J. C.; MacEachern, A.; Arnason, J. T.; Morand, P.; Hollebone, B.; Leitch, L. C.; Philogene, B. J. R. Photochem. Photobiol. 1986, 44, 441.
57. Reyftmann, J. P.; Kagan, J.; Santos, R.; Moliere, P. Photochem. Photobiol. 1985, 41, 1.
58. 57
59. 2. However, it is worth noting that oxygen has virtually no effect on the fluorescence of α-terthiophene, suggesting major differences between the photo-physics of oligomeric and polymeric thiophenes (see: Scaiano et al. Reference 59).
60. 0–0 transitions are ∼3.2 and 2.1 eV for anthracene (Berlman, I. B. Fluorescence Spectra of Aromatic Molecules; Academic: New York, 1971)
61. 1/2 for oxidation and reduction of anthracene are ∼−2.0 and +1.0 V (vs SCE), respectively (Meites, L.; Zuman, P. CRC Handbook Series in Organic Electrochemistry; CRC: Boca Raton, FL).
62. The onset for oxidation of P3HT is ∼+0.5 V (SCE) (Roncali, J.; Garreau, R.; Yassar, A.; Marque, P.; Gamier, F.; Lemaire, M. J. Phys. Chem. 1987, 91, 6706) which places the LUMO at —∼1.6 V and precludes any possibility of electron transfer between excited-state P3HT and anthracene on thermodynamic grounds.
63. Sugiyama, N.; Iwata, M.; Yoshioka, M.; Yamada, K.; Aoyama, H. J. Chem. Soc. 1969, 42, 1377.
64. 2 molecules react with the quencher before reverting to the ground state by other mechanisms.
65. 2.
66. Thompson, Q. E. J. Am. Chem. Soc. 1961, 83, 845.
67. Scheffer, J. R.; Ouchi, D. Tetrahedron Lett. 1970, 3, 223.
68. Neckers, D. C. J. Photochem. Photobiol. A 1989, 47, 1.
69. Skold, C. N.; Schlessinger, R. H. Tetrahedron. Lett. 1970, 791.
70. Wasserman, H. H.; Strehlow, W. Tetrahedron Lett. 1970, 795.
71. Gollnick, K. In Singlet Oxygen-Reaction with Organic Compounds and Polymers; Ranby, B., Rabek, L. F., Eds.; John Wiley: New York, 1978.
72. Adam, W.; Eggelte, H. J. Angew. Chem., Int. Ed. Engl. 1979, 17, 765.
73. Winslow, F. H.; Trozzolo, A. M. Macromolecules 1968, 1, 98.
74. Ogilby, P. R.; Dillon, M. P.; Kristiansen, M.; Clough, R. L. Macromolecules 1992, 25, 3399.
75. Bystritskaya, E. V.; Karpukhin, O. N. Vysokomol. Soedin., Ser. A 1976, 18, 1963.
76. Zwanenberg, B.; Wagenaar, A.; Strating, J. Tetrahedron Lett. 1970, 4683.
77. Richters, P. Macromolecules 1970, 3, 262.
78. Cicchetti, O. Adv. Polym. Sci. 1970, 3, 70.
79. McKeller, J. F.; Allen, N. S. Photochemistry of Man-Made Polymers; Applied Science Publishers: London, 1979; p 52.
80. Uri, N. Isr. J. Chem. 1970, 8, 125.
81. Beachell, H. C.; Nemphos, S. P. J. Polym. Sci. 1956, 21, 113.
82. Kujiai, C.; Hasiya, S.; Furuno, H.; Terada, N. J. Polym. Sci., Polym. Chem. Ed. 1968, 6, 589.
83. Tomozawa, H.; Braun, D.; Phillips, S.; Heeger, A. J.; Kroemer, H. Synth. Met. 1987, 22, 63.
84. Gamier, F.; Horowitz, G. Synth. Met. 1987, 18, 693.
85. Tomozawa, H.; Braun, D.; Phillips, S. D.; Worland, R.; Heeger, A. J.; Kroemer, H. Synth. Met. 1989, 28, C687.
86. Greenwood, N. N.; Gibb, T. C. Mossbouer Spectroscopy; Chapman and Hall: London, 1971.
87. Bajer, I. K.; Pawlicka, A.; Plenkiewicz, J.; Lefrant, S. Synth. Met. 1989, 39, 335.
88. Treinin, A. Isr. J. Chem. 1970, 8, 103.
89. Calvert, J. G.; Pitts, J. N., Jr. Photochemistry; John Wiley: New York, 1966.
90. Shiyapintokh, V. Ya. Photochemical Conversion and Stabilization of Polymers; Hanser: New York, 1984.
91. Reich, L.; Stivala, S. S. Autooxidation of Hydrocarbons and Polyolefins; Marcel Dekker: New York, 1969.
92. Carlsson, D. J.; Suprunchuk, T.; Wiles, D. M. Can. J. Chem. 1974, 52, 3728.