Synthesis of novel π-conjugated polymer having an enyne unit by palladium-catalyzed three-component coupling polymerization and subsequent retro-Diels-Alder reaction

Macromolecules

Volumn 33, Issue 5, 2000, Pages 1487-1488

  Choi, Cheol Kyu ^a   Tomita, Ikuyoshi ^a   Endo, Takeshi ^a  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; INFRARED SPECTROSCOPY; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; ORGANIC SOLVENTS; PALLADIUM; POLYMERIZATION; SYNTHESIS (CHEMICAL); TEMPERATURE; TOLUENE; VACUUM;

BISORGANOSTANNANE; DIIODOBENZENE; ENYNE UNIT; NORBORNADIENE; POLYDISPERSITY; RETRO DIELS-ALDER REACTION; THREE COMPONENT COUPLING POLYMERIZATION;

ORGANIC POLYMERS;

EID: 0033894231     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma991459k     Document Type: Article

References (34)

1. (a) Skotheim, T. A., Ed. Handbook of Conducting Polymers; Marcel Dekker: New York, 1986; Vol. 1.
2. (b) Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds. Handbook of Conducting Polymers, 2nd ed.; Marcel Dekker: New York, 1997.
3. (a) Baughman, R. H.; Bredas, J. L.; Chance, R. R.; Elsenbaumer, R. L.; Shacklette, L. W. Chem. Rev. 1982, 82, 209.
4. (b) Yamamoto, T. Prog. Polym. Sci. 1992, 17, 1153.
5. (c) Shi, G.; Xue, G.; Li, C.; Jin, S.; Yu, B. Macromolecules 1994, 27, 3679.
6. (d) Kaeriyama, K.; Mehta, M. A.; Masuda, H. Synth. Met. 1995, 69, 507.
7. (e) Ofer, D.; Swager, T. M.; Wrighton, M. S. Chem. Mater. 1995, 7, 418.
8. (f) Nehring, J.; Amstutz, H.; Holmes, P. A.; Nevin, A. Appl. Phys. Lett. 1987, 51, 1283.
9. (g) Witteler, H.; Lieser, G.; Wegner, G.; Schulze, M. Makromol. Chem., Rapid Commun. 1993, 14, 471.
10. (h) 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.
11. (i) Hilberer, A.; Brouwer, H.; van der Scheer, B.-J.; Wildeman, J.; Hadziioannou, G. Macromolecules 1995, 28, 4525.
12. (j) Meghdadi, F.; Leising, G.; Fischer, W.; Stelzer, F. Synth. Met. 1996, 76, 113.
13. (k) Yamamoto, T.; Yamada, W.; Takagi, M.; Kizu, K.; Maruyama, T.; Ooba, N.; Tomaru, S.; Kurihara, T.; Kaino, T.; Kubota, K. Macromolecules 1994, 27, 6620.
14. (l) Wautelet, P.; Moroni, M.; Oswald, L.; Le Moigne, J.; Pham, A.; Bigot, J.-Y.; Luzzati, S. Macromolecules 1996, 29, 446.
15. (a) Rehahn, M.; Schlüter, A.-D.; Wegner, G.; Feast, W. J. Polymer 1989, 30, 1060.
16. (b) Fahnenstich, U.; Koch, K.-H.; Müllen, K. Makromol. Chem., Rapid Commun. 1989, 10, 563.
17. (a) Bao, Z.; Chan, W.; Yu, L. Chem. Mater. 1993, 5, 2.
18. (b) Bochmann, M.; Kelly, K. J. Chem. Soc., Chem. Commun. 1989, 532.
19. (c) Moore, J. S. Makromol. Chem., Rapid Commun. 1992, 13, 563.
20. Hong, L.; Douglas, R.; Powell, R.; Hayashi, K.; Robert, W. Macromolecules 1998, 31, 52.
21. (a) Suzuki, M.; Saegusa, T. Macromolecules 1990, 23, 1574.
22. (b) Greiner, A.; Heitz, W. Makromol. Chem., Rapid Commun. 1988, 9, 581.
23. (c) Weitzel, H.-P.; Müllen, K. Makromol. Chem. 1990, 191, 2837.
24. (a) Miyaki, N.; Tomita, I.; Endo, T. Macromolecules 1996, 29, 6685.
25. (b) Miyaki, N.; Tomita, I.; Endo, T. J. Polym. Sci., Part A: Polym. Chem. 1997, 359, 2097.
26. (c) Miyaki, N.; Tomita, I.; Endo, T. Macromolecules 1997, 30, 4504.
27. (d) Miyaki, N.; Tomita, I.; Endo, T. Chem. Lett. 1997, 685.
28. Miyaki, N.; Tomita, I.; Endo, T. Polym. Bull. 1997, 39, 677.
29. (a) Kosugi, M.; Tamura, H.; Sano, H.; Migita, T. Chem. Lett. 1987, 193.
30. (b) Kosugi, M.; Kimura, T.; Oda, H.; Migita, T. Bull. Chem. Soc. Jpn. 1993, 66, 3522.
31. 4 (0.0231 g, 0.01 mmol), 1 (0.165 g, 0.50 mmol), 2 (0.9214 g, 10 mmol), 3 (0.226 g, 0.5 mmol), and toluene (2 mL), and the mixture was kept stirring at ambient temperature for 15 min under nitrogen. The tube was then sealed under reduced pressure. After the reaction at 100 °C for 2 days, the reaction mixture was precipitated with methanol and then with n-hexane. The precipitate was freeze-dried from benzene. 4: yield 82% (0.156 g, 0.41 mmol).
32. 24: C, 93.71%; H, 6.29%. Found: C, 91.58%; H, 6.42%; Cl, 0.55%. The observed lower carbon content is most probably due to contamination of the palladium catalyst.
33. To estimate the thermal stability of the model compound (cis, exo-1,4-bis[2-{2-(4-dodecyloxyphenyl)bicyclo[2,2,1]heptenyl}ethynyl]benzene), TGA analysis was carried out under nitrogen (at a heating rate of 10 °C/min), from which the weight loss started at 178 °C and the 10% weight loss was observed at 231 °C.
34. TGA data of the polymer 4 (taken at a heating rate of 10 °C/min) indicate that the retro-Diels-Alder reaction proceeded at lower temperature compared with that of the model compound. This difference might be explained by the difference in the thermodynamic energy between the starting norbornene and enyne derivatives.