Segmented poly[2-methoxy-5-(2-ethylhexyloxy)-1,4-phenylene vinylene] via xanthate and dithiocarbamate precursors: A comparative study of thermal eliminations

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 41, Issue 24, 2003, Pages 3929-3940

  Padmanaban, G ^a   Nagesh, K ^a   Ramakrishnan, S ^a  

^a INDIAN INSTITUTE OF SCIENCE   (India)

Author keywords

Activation energy; Conjugated polymers; Fluorescence

Indexed keywords

ACTIVATION ENERGY; COMPOSITION; FLUORESCENCE; LIGHT ABSORPTION; MOLECULAR STRUCTURE; POLYELECTROLYTES; QUANTUM THEORY; REACTION KINETICS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL); THERMAL EFFECTS;

DITHIOCARVAMATE; NUCLEOPHILIC SUBSTITUTION; POLYMETHOXY ETHYLHEXYLOXY PHENYLENE VINYLENE; THERMAL ELIMINATION KINETICS; ULTRA VIOLET SPECTRA; XANTHATE;

AROMATIC POLYMERS;

POLYMER SCIENCE;

EID: 0346266259     PISSN: 0887624X     EISSN: None     Source Type: Journal    
DOI: 10.1002/pola.10974     Document Type: Article

References (63)

1. Burroughes, J. H.; Bradley, D. D. C.; Brown, A. R.; Marks, H. N.; Mackay, K.; Friend, R. H.; Burns, P. L.; Holmes, A. B. Nature 1990, 347, 539.
2. Braun, D.; Heeger, A. J. Appl Phys Lett 1991, 58, 1982.
3. Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew Chem Int Ed Engl 1998, 37, 402.
4. Friend, R. H.; Gymer, R. W.; Holmes, A. B.; Burroughes, J. H.; Marks, R. N.; Taliani, C.; Bradley, D. D. C.; dos Santos, D. A.; Bredas, J. L.; Logdlund, M.; Salaneck, W. R. Nature 1999, 397, 121.
5. Narayan, K. S.; Singh, Th.B. Appl Phys Lett 1999, 74, 3456.
6. Halls, J. J. M.; Walsh, C. A.; Greenham, N. C.; Holmes, A. B.; Marsegila, E. A.; Friend, R. H.; Moratti, S. C. Nature 1995, 376, 498.
7. Kohler, A.; dos Santos, D. A.; Beljonne, D.; Shuai, Z.; Bredas, J. L.; Holmes, A. B.; Kraus, A.; Mullen, K.; Friend, R. H. Nature 1998, 392, 903.
8. Tessler, N.; Denton, G. J.; Friend, R. H. Nature 1995, 382, 695.
9. Hide, F.; Diaz-Garica; Schwartz, B. J.; Andersson, M. R.; Pai, Q.; Heeger, A. J. Science 1996, 273, 1833.
10. Tessler, N. Adv Mater 1999, 11, 363.
11. Granstrom, M.; Petritsch; Arias, A. C.; Lux; Anderson, M. R.; Friend, R. H. Nature 1998, 395, 257.
12. Sirringhaus, H.; Tessler, N.; Friend, R. H. Science 1998, 280, 1741.
13. Yu, G.; Wang, J.; McElvain, J.; Heeger, A. J. Adv Mater 1998, 10, 1431.
14. Pei, Q.; Yu, G.; Zhang, C.; Yang, Y.; Heeger, A. J. Science 1995, 269, 1086.
15. Pei, Q.; Yang, Y.; Yu, G.; Zhang, C.; Heeger, A. J. J Am Chem Soc 1996, 118, 3922.
16. Wessling, R. A.; Zimmerman, R. G. U.S. Patent 3,401,152, 1968.
17. Montaudo, G.; Vitalini, D.; Lenz, R. W. Polymer 1987, 28, 837.
18. Lenz, R. W.; Han, C.-C.; Stenger-Smith, J.; Karasz, F. E. J Polym Sci Part A: Polym Chem 1988, 26, 3241.
19. Gilch, H. G.; Wheelwright, W. L. J Polym Sci Part A-1: Polym Chem 1966, 4, 1337.
20. Wudl, F.; Allemand, P. M.; Srdanov, G.; Ni, Z.; McBranch, D. ACS Symposium Series 455; American Chemical Society: Washington, DC, 1991; p 683.
21. Hsieh, B. R.; Yu, Y.; Lee, H. K.; VanLaeken, A. C. Macromolecules 1997, 30, 6567.
22. Son, S.; Dodabalapur, A.; Lovinger, A. J.; Galvin, M. E. Science 1995, 269, 376.
23. Lo, S. C.; Sheridan, A.; Samuel, I D. W.; Burn, P. L. J Mater Chem 1999, 9, 2165.
24. Lo, S. C.; Sheridan, A.; Samuel, I. D. W.; Burn, P. L. J Mater Chem 2000, 10, 275.
25. Lo, S. C.; Palsson, L. O.; Kilitziraki, M.; Burn, P. L.; Samuel, I. D. W. J Mater Chem 2001, 11, 2228.
26. Louwet, F.; Vanderzande, D.; Gelan, J.; Mullens, J. Macromolecules 1995, 28, 1330.
27. Issaris, A.; Vanderzande, D.; Adriaensens, P.; Gelan, J. Macromolecules 1998, 31, 4426.
28. Heitz, W.; Bruegging, W.; Freund, L.; Gailberger, M.; Grainer, A.; Jung, H.; Kampschulte, U.; Niessner, N.; Osan, F. Makromol Chem 1988, 189, 119.
29. Pan, M.; Bao, Z.; Yu, L. Macromolecules 1995, 28, 5151.
30. Burn, P. L.; Holmes, A. B.; Kraft, A.; Bradley, D. D. C.; Brown, A. R.; Friend, R. H.; Gymer, R. W. Nature 1992, 356, 47.
31. Koßmehl, G.; Samandari, M. Makromol Chem 1984, 185, 1517.
32. El-Ghayoury, A.; Schenning, A. P. H. J.; Meijer, E. W. J Polym Sci Part A: Polym Chem 2002, 40, 4020.
33. Spiliopoulos, I. K.; Mikroyannidis, J. A. J Polym Sci Part A: Polym Chem 2002, 40, 2591.
34. Zheng, M.; Ding, L.; Gurel, E. E.; Karasz, F. E. J Polym Sci Part A: Polym Chem 2002, 40, 235.
35. Zhu, K.; Xie, Z.; Wang, L.; Jing, X.; Wang, F. J Polym Sci Part A: Polym Chem 2002, 40, 1321.
36. Tokita, S.; Momii, T.; Murata, H.; Tsutsui, T.; Saito, S. Polymer 1990, 31, 1137.
37. Burn, P. L.; Bradley, D. D. C.; Brown, A. R.; Friend, R. H.; Holmes, A. B. Synth Met 1991, 41-43, 261.
38. Gowri, R.; Mandal, D.; Shivkumar, B.; Ramakrishnan, S. Macromolecules 1998, 31, 1819.
39. Gowri, R.; Padmanaban, G.; Ramakrishnan, S. Synth Met 1999, 101, 166.
40. Padmanaban, G.; Ramakrishnan, S. J Am Chem Soc 2000, 122, 2244.
41. Braun, D.; Staring, E. G. J.; Demandt, R. C. J. E.; Rikken, G. L. J.; Kessener, Y. A. R. R.; Venhuizen, A. H. J. Synth Met 1994, 66, 75.
42. A preliminary report of the xanthate precursor approach appeared in: Padmanaban, G.; Ramakrishnan, S. Synth Met 2001, 119, 536.
43. Continued stirring after addition of the nucleophile solution promoted rapid coagulation and precipitation of the polymer, which in many cases leads only to partially soluble products.
44. Because the molar fraction was taken with respect to the sulfonium monomer, the reason for the apparently higher slope (>1) was the formation of significant amounts of various uncharacterized low-molecular-weight species during the polymerization, and the actual partitioning of the nucleophile utilization between the polymer (whose yield was in the range of 25-40%) and the other products is unknown. Hence, this apparently higher slope suggests a preferential utilization of the xanthate toward the polymeric sulfonium species.
45. O'Connor, G. L.; Nace, H. R. J Am Chem Soc 1952, 74, 5454.
46. O'Connor, G. L.; Nace, H. R. J Am Chem Soc 1953, 75, 2118.
47. Marletta, A.; Goncalves, D.; Oliveira, O. N., Jr.; Faria, R. M.; Guimaraes, F. E. G. Adv Mater 2000, 12, 69.
48. Stalmach, U.; Kolshorn, H.; Brehm, I.; Meier, H. Liebigs Ann Chem 1996, 1449.
49. Meier, H.; Stalmach, U.; Kolshorn, H. Acta Polym 1997, 48, 379.
50. max) because we are always dealing with a distribution of conjugation lengths; therefore, the spectra represent several overlapping peaks because of the oligomers of varying conjugation lengths.
51. Shah, H.; Arbuckle, G. Macromolecules 1999, 32, 1413.
52. Kesters, E.; Gillissen, S.; Motmans, F.; Lutsen, L.; Vanderzande, D. Macromolecules 2002, 35, 7902.
53. 1H NMR spectra of solution-eliminated MEH-PPV samples (MXP-100 and MDP-100) were devoid of a peak at about 6.8 ppm, which is where the protons linked to a cis double bond are expected. The presence of cis double bonds in thin-film eliminated samples of MEH-PPV samples, prepared via either of the precursors, was difficult to detect with IR spectroscopy because of the presence of other bands in the same region, where the cis-specific peaks were to be expected. Further, because solid-state eliminated samples wre insoluble, they were not amenable to solution NMR characterization.
54. For spectral details, refer to the Supplementary Material.
55. Hu, D.; Yu, J.; Padmanaban, G.; Ramakrishnan, S.; Barbara, P. F. Nano Lett 2002, 2, 1121.
56. Candeias, L. P.; Grozema, F. C.; Padmanaban, G.; Ramakrishnan, S.; Siebbeles, L. D. A.; Warman, J. M. J Phys Chem B 2003, 107, 1554.
57. van Haare, J. A. E. H.; Padmanaban, G.; Ramakrishnan, S. Manuscript under preparation.
58. Padmanaban, G.; Ramakrishnan, S. Manuscript under preparation.
59. 99 values were calculated with the respective experimentally determined rate constants.
60. 99 at 200 °C to be about 24 h.
61. Otsu, T. J Polym Sci Part A: Polym Chem 2000, 38, 2121.
62. Quinn, J. F.; Chaplin, R. P.; Davis, T. P. J Polym Sci Part A: Polym Chem 2002, 40, 2956.
63. Farmer, S. C.; Patten, T. E. J Polym Sci Part A: Polym Chem 2002, 40, 555.