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http://dx.doi.org/10.5012/bkcs.2009.30.2.309

Synthesis and Characterization of Poly(arylene-ethynylene)s with Ferrocene Unit by Reaction of 1,1'-Bis(ethynyldimethylsilyl)ferrocene and Aromatic Dihalides  

Lee, In-Sook (Faculty of Liberal Education, Kyungpook National University)
Lee, Chong-Gu (Department of Chemistry, Kyungpook National University)
Kwak, Young-Woo (Department of Chemistry, Kyungpook National University)
Gal, Yeong-Soon (Polymer Chemistry Laboratory, College of Engineering, Kyungil University)
Publication Information
Abstract
New poly(arylene-ethynylene)s with silicon-containing ferrocene moiety in the polymer main chain were synthesized via the C-C bond forming reactions of 1,1´-bis(ethynyldimethylsilyl)ferrocene and various aromatic dihalides in high yields. The aromatic dihalides include 1,4-dibromobenzene, 4,4´-dibromobiphenyl, 9,10-dibromoanthracene, 2,5-dibromopyridine, 2,5-dibromothiophene, and 2,6-diiodo-4-nitroaniline. The polymer structures and properties were characterized by such instrumental methods as NMR $(^1H-,\;^{13}C-,\;and\;^{29}Si-)$, IR, UV-visible spectroscopies and TGA/DSC. The spectral data indicated that the present polymers have the regular alternating structure of 1,1´-bis(ethynyldimethylsilyl)ferrocenylene and arylene units. The resulting polymers were completely soluble in such organic solvents as methylene chloride, chloroform, benzene, chlorobenzene, and THF. The thermal behaviors of the resulting polymers were examined.
Keywords
Aromatic dihalides; 1,1´-Bis(ethynyldimethylsilyl)ferrocene; Coupling reaction; Poly(aryleneethynylene); Palladium catalyst;
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1 Choi, S. K.; Gal, Y. S.; Jin, S. H.; Kim, H. K. Chem. Rev. 2000, 100, 1645   DOI   ScienceOn
2 Rutledge, T. F., Ed.; Acetylenic Compounds: Preparation and Substitution Reactions; Reinhold Book Corporation: New York, 1968
3 Chauser, M. G.; Rodionov, Yu. M.; Misin, V. M.; Cherkashin, M. I. Russ. Chem. Rev. 1976, 45, 348   DOI   ScienceOn
4 Bu'Lock, J. D. Progress in Organic Chemistry 1964, 6, 86
5 Jones, E. R. H.; Skattebol, L.; Whiting, M. C. J. Chem. Soc. 1958, 1054   DOI
6 Eglinton, G.; Galbraith, A. R. J. Chem. Soc. 1959, 889   DOI
7 Kim, J. H.; Park, Y. T. Bull. Korean Chem. Soc. 2006, 27, 869   DOI   ScienceOn
8 Greenham, S. C.; Moratti, S. C.; Bradley, D. D. C.; Friend, R. H.; Holmes, A. B. Nature 1993, 365, 628.   DOI   ScienceOn
9 Jin, S. H.; Kim, M. Y.; Kim, J. Y.; Lee, K.; Gal, Y. S. J. Am. Chem Soc. 2004, 126, 2474   DOI   ScienceOn
10 Lam, J. K. Y.; Tang, B. Z. Acc. Chem. Res. 2005, 38, 745   DOI   ScienceOn
11 Masuda, T. J. Polym. Sci.: Part A: Polym. Chem. 2007, 45, 165   DOI   ScienceOn
12 Shirota, Y.; Kageyama, H. Chem. Rev. 2007, 107, 953   DOI   ScienceOn
13 Lo, S. C.; Burn, P. L. Chem. Rev. 2007, 107, 1097   DOI   ScienceOn
14 Thomas III, S. W.; Joly, G. D.; Swager, T. M. Chem. Rev. 2007, 107, 1339   DOI   ScienceOn
15 Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem. Int. Ed. 1998, 37, 402   DOI   ScienceOn
16 Gal, Y. S.; Lee, I. S.; Chang, E. H.; Jeong, Y. C.; Kwak, Y. W. Bull. Korean Chem. Soc. 2007, 28, 1305   DOI   ScienceOn
17 Tang, C. W.; VanSlyke, S. A. Appl. Phys. Lett. 1987, 51, 913   DOI
18 Burroughes, J. H.; Bradey, D. D. C.; Brown, A. R.; Marks, R. N.; Mackay, K.; Triend, R. H.; Burns, P. L.; Holmes, A. Nature 1990, 347, 539.   DOI
19 Jeon, H. S.; Lee, S. K.; Lee, E. J.; Park, S. M.; Kim, S. C.; Jin, S. H.; Gal, Y. S.; Lee, J. W.; Im, C. Macromolecules 2007, 40, 4794   DOI   ScienceOn
20 Yang, J. S.; Swager, T. M. J. Am. Chem. Soc. 1998, 120, 11864   DOI   ScienceOn
21 Cassar, I. J. Organomet. Chem. 1975, 93, 253   DOI   ScienceOn
22 Montali, A.; Bastiaansen, G.; Smith, P.; Weder, C. Nature 1998, 392, 261   DOI   ScienceOn
23 Bunz, U. H. F. Chem. Rev. 2000, 100, 1605   DOI   ScienceOn
24 Dieck, H. A.; Heck, R. F. J. Organomet. Chem. 1975, 93, 259   DOI   ScienceOn
25 Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467   DOI   ScienceOn
26 Corriu, R. J. P.; Douglas, W. E.; Yang, Z.-X. J. Polym. Sci. Pt.CPoly. Lett. 1990, 28, 431   DOI   ScienceOn
27 Iwahara, T.; Hayase, S.; West, R. Macromolecules 1990, 23, 1298   DOI
28 Ishikawa, M.; Horio, T.; Hatano, T.; Kunai, A. Organometallics 1993, 12, 2078   DOI   ScienceOn
29 Komaguchi, K.; Shiotani, M.; Ishikawa, M. Macromolecules 1998, 31, 985
30 Ohshita, J.; Yoshimoto, K.; Tada, Y.; Harima, Y.; Kunai, A.; Kunugi, Y.; Yamashita, K. J. Organomet. Chem.. 2003, 678, 33   DOI   ScienceOn
31 Kim, H. K.; Ryu, M. K.; Lee, S. M. Macromolecules 1997, 30, 1236   DOI   ScienceOn
32 Kim, K. D.; Park, J. S.; Kim, H. K.; Lee, T. B.; No, K. T. Macromolecules 1998, 31, 7267   DOI   ScienceOn
33 Corriu, R. J. P.; Douglas, W. E.; Yang, Z.-X. J. Organomet. Chem. 1993, 456, 35   DOI   ScienceOn
34 Kwak, Y. W.; Lee, K. K.; Cha, S. H.; Lee, S. K.; Lee, I. S.; Park, Y. T.; Lee, J.; Yoh, S. D.; Kim, W. S. Bull. Korean Chem. Soc. 2003, 24, 479   DOI   ScienceOn
35 Lee, S. G.; Kwak, Y. W.; Park, J. W.; Jin, S. H.; Gal, Y. S. J. Nonlinear Opt. Phys. & Mater. 2005, 14, 573   DOI   ScienceOn
36 Corriu, R. J. P.; Devylder, N.; Guérin, C.; Henner, B.; Jean, A. Organometallics 1994, 13, 3194   DOI   ScienceOn
37 Jain, R.; Choi, H.; Lalancette, R. A.; Sheridan, J. B. Organometallics 2005, 24, 1468   DOI   ScienceOn
38 Kan, P. T.; Lenk, C. T.; Schaaf, R. L. J. Org. Chem. 1961, 26, 4038   DOI
39 Corriu, R. J. P.; Douglas, W. E.; Yang, Z. X.; Karakus, Y.; Cross, G. H.; Bloor, D. J. Organomet. Chem. 1993, 455, 69   DOI   ScienceOn
40 Corriu, R. J. P.; Douglas, W. E.; Yang, Z.-X.; Garnier, F.; Yassar, A. J. Organomet. Chem. 1991, 417, C50   DOI   ScienceOn
41 Kunai, A.; Toyoda, E.; Horata, K.; Ishikawa, M. Organometallics 1995, 14, 714   DOI   ScienceOn
42 Manhart, S. A.; Adachi, A.; Sakamaki, K.; Okita, K.; Ohshita, J.; Ohno, T.; Hamaguchi, T.; Kunai, A.; Kido, J. J. Organomet. Chem. 1999, 592, 52   DOI   ScienceOn
43 Lee, S. G.; Kwak, Y. W.; Koo, B. K.; Jin, S. H.; Gal, Y. S. Mol. Cryst. Liq. Cryst. 2006, 458, 237   DOI   ScienceOn