Polyaddition of 2,7-diethynyl-9,9-dioctylfluorene using regio- and stereoselective alkyne dimerization catalysts

Macromolecules

Volumn 37, Issue 1, 2004, Pages 13-17

  Katayama, Hiroyuki ^a   Nakayama, Mari ^a   Nakano, Tadashi ^a   Wada, Chikaya ^a   Akamatsu, Kensuke ^b   Ozawa, Fumiyuki ^a,c  

^a Osaka Prefecture University   (Japan)

^b KONAN UNIVERSITY   (Japan)

^c KYOTO UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYST SELECTIVITY; CHLORINE COMPOUNDS; FLUORINE CONTAINING POLYMERS; ISOMERS; PALLADIUM; POLYMERIZATION; RHODIUM; RUTHENIUM COMPOUNDS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); THERMODYNAMIC STABILITY;

DIETHYNYL DIOCTYLFLUORENE; DIMESITYLIMIDAZOLINIUM CHLORIDE; POLYADDITION;

VINYL RESINS;

EID: 1642578134     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma035181e     Document Type: Article

References (43)

1. (a) Bernius, M. T.; Inbasekaran, M.; O'Brien, J.; Wu, W. Adv. Mater. 2000, 12, 1737-1750.
2. (b) Bunz, U. H. F. Chem. Rev. 2000, 100, 1605-1644.
3. (c) 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.; Brédas, J. L.; Löglund, M.; Salaneck, W. R. Nature (London) 1999, 397, 121-128.
4. (d) Yamamoto, T. Bull. Chem. Soc. Jpn. 1999, 72, 621-638.
5. (e) Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem., Int. Ed. 1998, 37, 402-428.
6. Son, S.; Dodabalapur, A.; Lovinger, A. J.; Galvin, M. E. Science 1995, 269, 376-378.
7. (a) Liao, L.; Pang, Y.; Ding, L.; Karasz, F. E. Macromolecules 2001, 34, 6756-6760.
8. (b) Pang, Y.; Li, J.; Hu, B.; Karasz, F. E. Macromolecules 1999, 32, 3946-3950.
9. (a) Late Transition Metal Polymerization Catalysis; Rieger, B., Baugh, L., Kacker, S., Striegler, S. Eds.; Wiley-VCH: Weinheim, 2003.
10. (b) Transition Metal Catalysis in Macromolecular Design; Boffa, L. S., Novak, B. M. Eds.; ACS Symp. Ser. 760; American Chemical Society: Washington, DC, 2000.
11. Katayama, H.; Nagao, M.; Moriguchi, R.; Ozawa, F. J. Organomet. Chem. 2003, 676, 49-54.
12. (a) Mori, A.; Takahisa, E.; Kajiro, H.; Nishihara, Y.; Hiyama, T. Macromolecules 2000, 33, 1115-1116.
13. (b) Mori, A.; Takahisa, E.; Kajiro, H.; Nishihara, Y.; Hiyama, T. Polyhedron 2000, 19, 567-568.
14. Rhodium-catalyzed polyaddition of diethylnylsilanes has been reported. See: Ohshita, J.; Matsuguchi, A.; Furumori, K.; Hong, R.-F.; Ishikawa, M.; Yamanaka, T.; Koike, T.; Shioya, J. Macromolecules 1992, 25, 2134-2140.
15. During preparation of this manuscript, Hou et al. independently reported a similar polyaddition system using lanthanide catalysts: Nishiura, M.; Tanikawa, M.; Hoshino, M.; Hou, Z. 83th Annual Meeting of the Chemical Society of Japan, Tokyo, Japan, March 2003; Abstracts II 3C5-38.
16. (a) Choi, C.-K.; Tomita, I.; Endo, T. Macromolecules 2000, 33, 1487-1488.
17. (b) Venkatesan, D.; Yoneda, M.; Ueda, M. React. Funct. Polym. 1996, 30, 341-352.
18. (a) Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: New York, 1995.
19. (b) Henkelmann, J. In Applied Homogeneous Catalysis with Organometallic Compounds; Cornils, B., Hermann, W. A. Eds.; VCH: New York, 1996.
20. For the recent reports on transition-metal-catalyzed dimerization of terminal alkynes, see: Nishiura, M.; Hou, Z.; Wakatsuki, Y.; Yamaki, T.; Miyamoto, T. J. Am. Chem. Soc. 2003, 125, 1184-1185.
21. (b) Yang, C.; Nolan, S. P. J. Org. Chem. 2002, 67, 591-593.
22. (c) Melis, K.; Samulkiewicz, P.; Rynkowski, J.; Verpoort, F. Tetrahedron Lett. 2002, 43, 2713-2716.
23. (d) Dash, A. K.; Gourevich, I.; Wang, J. Q.; Wang, J.; Kapon, M.; Eisen, M. S. Organometallics 2001, 20, 5084-5104.
24. (e) Esteruelas, M. A.; Herrero, J.; López, A. M.; Oliván, M. Organometallics 2001, 20, 3202-3205.
25. (f) Baratta, W.; Zotto, A. D.; Herdtweck, E.; Vuano, S.; Rigo, P. J. Organomet. Chem. 2001, 617-618, 511-519.
26. Boese, W. T.; Goldman, A. S. Organometallics 1991, 10, 782-786.
27. (a) Ohmura, T.; Yorozuya, S.-i.; Yamamoto, Y.; Miyaura, N. Organometallics 2000, 19, 365-367.
28. (b) Qü, J.-P.; Masui, D.; Ishii, Y.; Hidai, M. Chem. Lett. 1998, 1003-1004.
29. (c) Yi, C. S.; Liu, N. Organometallics 1996, 15, 3968-3971.
30. Katayama, H.; Ozawa, F. Organometallics 1998, 17, 5190-5196.
31. Details of alkyne dimerization using 3/N-methylpyrrolidine as a catalyst will be reported elsewhere.
32. Yi, C. S.; Liu, N.; Rheingold, A. L.; Liable-Sands, L. M. Organometallics 1997, 16, 3910-3913.
33. 2 afforded (Z)-1,4-diphyenyl-1-butene-3-yne in 84, 46, and 37% yields (GLC), respectively, under the reaction conditions identical to eq 1.
34. (a) Zhan, X.; Liu, Y.; Wu, X.; Wang, S.; Zhu, D. Macromolecules 2002, 35, 2529-2537.
35. (b) Inaoka, S.; Advincula, R. Macromolecules 2002, 35, 2426-2428.
36. (c) Lee, S. H.; Nakamura, T.; Tsutsui, T. Org. Lett. 2001, 3, 2005-2007.
37. (d) Johansson, D. M.; Theander, M.; Granlund, T.; Inganäs, O.; Andersson, M. R. Macromolecules 2001, 34, 1981-1986 and references therein.
38. Ricks, H. L.; Choudry, U. H.; Marshall, A. R.; Bunz, U. H. F. Macromolecules 2003, 36, 1424-1425.
39. For the synthesis and properties of cross-conjugated polymers, see: Zhao, Y.; Campbell, K.; Tykwinski, R. R. J. Org. Chem. 2002, 67, 336-344 and references cited therein.
40. Kreyenschmidt, M.; Klaerner, G.; Fuhrer, T.; Ashenhurst, J.; Karg, S.; Chen,W. D.; Lee, V. Y.; Scott, J. C.; Miller, R. D. Macromolecules 1998, 31, 1099-1103.
41. Takahashi, S.; Kuroyama, Y.; Sonogashira, K.; Hagihara, N. Synthesis 1980, 627-630.
42. Arduengo, A. J., III; Krafczyk, R.; Schmutzler, R.; Craig, H. A.; Goerlich, J. R.; Marshall, W. H.; Unverzagt, M. Tetrahedron 1999, 55, 14523-14534.
43. Echavarren, A. M.; Löpez, J.; Santos, A.; Montoya, J. J. Organomet. Chem. 1991, 414, 393-400.