Synthesis of soluble poly(para-phenylene) with a long polymer chain: Characteristics of regioregular poly(1,4-phenylene)
Corresponding Author
Itaru Natori
Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-chou, Koganei-city, Tokyo 184-8588, Japan
Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-chou, Koganei-city, Tokyo 184-8588, JapanSearch for more papers by this authorShizue Natori
Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-chou, Koganei-city, Tokyo 184-8588, Japan
Search for more papers by this authorHiroyuki Sekikawa
Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-chou, Koganei-city, Tokyo 184-8588, Japan
Search for more papers by this authorHisaya Sato
Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-chou, Koganei-city, Tokyo 184-8588, Japan
Search for more papers by this authorCorresponding Author
Itaru Natori
Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-chou, Koganei-city, Tokyo 184-8588, Japan
Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-chou, Koganei-city, Tokyo 184-8588, JapanSearch for more papers by this authorShizue Natori
Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-chou, Koganei-city, Tokyo 184-8588, Japan
Search for more papers by this authorHiroyuki Sekikawa
Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-chou, Koganei-city, Tokyo 184-8588, Japan
Search for more papers by this authorHisaya Sato
Department of Organic and Polymer Materials Chemistry, Tokyo University of Agriculture & Technology, 2-24-16 Naka-chou, Koganei-city, Tokyo 184-8588, Japan
Search for more papers by this authorAbstract
Soluble poly(para-phenylene) having a long polymer chain (more than six repeat units) was synthesized with a tert-butyl end-group (t-PPP) and was found to have improved solubility and excellent optical properties. Poly(1,3-cyclohexadiene) (PCHD) consisting of only 1,4-cyclohexadiene (1,4-CHD) units was synthesized with a tert-butyl end-group (t-PCHD), and completely dehydrogenated to obtain t-PPP. This end-group effectively prevented the crystallization of t-PPP, and polymers containing up to 16 repeat units were soluble in tetrahydrofuran. Soluble t-PPP obtained had an ability to form a tough thin film prepared by spin-coating method. Optical analyses of t-PPP provided strong evidence for a linear polymer chain structure. A block copolymer of t-PPP and a soluble polyphenylene (PPH) was then synthesized, and the excellent optical properties were retained by this block copolymer along with its solubility. © 2008 Wiley Periodicals, Inc. J Polym Sci Part A: Polym Chem 46: 5223–5231, 2008
REFERENCES AND NOTES
- 1 Kovacic, P.;Jones, M. B. Chem Rev 1987, 87, 357–359.
- 2 Ivory, D. M.;Miller, G. G.;Sowa, J. M.;Shacklette, L. W.;Chance, R. R.;Baughman, R. H. J Chem Phys 1979, 71, 1506–1507.
- 3 Grem, G.;Leditzky, G.;Ullrich, B.;Leising, G. Adv Mater 1992, 4, 36–37.
- 4 Grem, G.;Leditzky, G.;Ullrich, B.;Leising, G. Synth Met 1992, 51, 383–389.
- 5 Grem, G.;Leising, G.; Synth Met 1993, 57, 4105–4110.
- 6 Ried, W.;Freitag, D. Angew Chem Int Ed Engl 1968, 7, 835–844.
- 7 Edwards, A.;Blumstengal, S.;Sokolik, I.;Dorsinville, R.;Yun, H.;Kwei, T. K.;Okamoto, Y. Appl Phys Lett 1997, 70, 298–300.
- 8 Biyao, W.;Yamamoto, T. J.; Appl Polym Sci 2003, 89, 2210.
- 9 Marvel, C. S.;Hartzell, G. E. J Am Chem Soc 1959, 81, 448–452.
- 10 Frey, D. A.;Hasegawa, M.;Marvel, C. S. J Polym Sci Part A: Polym Chem 1963, 1, 2057–2065.
- 11 Lefebver, G.,Dawans, F. J Polym Sci Part A: Polym Chem 1964, 2, 3277–3295.
- 12 Zhong, X. F.;François, B. Makromol Chem Rapid Commun 1988, 9, 411–416.
- 13 Zhong, X. F.;François, B. Synth Met 1989, 29, 35–40.
- 14 Zhong, X. F.;François, B.; Synth Met 1991, 41–43, 955–958.
- 15 Zhong, X. F.;François, B. Makromol Chem 1991, 192, 2277–2291.
- 16 François, B.;Widawski, G.;Rawiso, M.;Cesar, B.; Synth Met 1995, 69, 463–466.
- 17
Si-Ahmed, L.;Nüesch, F.;Zuppiroli, L.;François, B.
Macromol Chem Phys
1998,
199,
625–632.
10.1002/(SICI)1521-3935(19980401)199:4<625::AID-MACP625>3.0.CO;2-5 CAS Web of Science® Google Scholar
- 18 François, B.;Izzillo, S.;Iratçabal, P. Synth Met 1999, 102, 1211–1212.
- 19 Mignard, E.;Tachon, C.;François, B. Synth Met 1999, 102, 1246–1247.
- 20 Williamson, D. T.;Buchanan, T. D.;Long, T. E. Polymer Preprints 2002, 43 (2), 1201–1202.
- 21 Mignard, E.;Hiorns, R. C.;François, B. Macromolecules 2002, 35, 6132–6141.
- 22 Natori, I.;Sato, H. J Polym Sci Part A: Polym Chem 2006, 44, 837–845.
- 23 Natori, I.;Sato, H. J Polym Sci Part A: Polym Chem 2006, 44, 3526–3537.
- 24 Cassidy, P. E.;Marvel, C. S. J Polym Sci Part A: Polym Chem 1965, 3, 1533–1565.
- 25 Mango, L. A.;Lenz, R. W. Makromol Chem 1973, 163, 13–36.
- 26 François, B.;Zhong, X. F. Makromol Chem 1990, 191, 2743–2753.
- 27 Natori, I. Macromolecules 1997, 30, 3696–3697.
- 28 Natori, I.;Inoue, S. Macromolecules 1998, 31, 982–987.
- 29 Natori, I.;Inoue, S. Macromolecules 1998, 31, 4687–4694.
- 30 Natori, I.;Imaizumi, K. Macromol Symp 2000, 157, 143–150.
- 31
Natori, I.;Imaizumi, K.;Yamagishi, H.;Kazunori, M.
J Polym Sci Part B: Polym Phys
1998,
36,
1657–1668.
10.1002/(SICI)1099-0488(19980730)36:10<1657::AID-POLB7>3.0.CO;2-M CAS Web of Science® Google Scholar
- 32 Natori, I.;Natori, S.;Sato, H. Macromolecules 2006, 39, 3168–3174.
- 33 Natori, I.;Natori, S.;Sato, H. Polymer 2006, 47, 7123–7130.
- 34 Natori, I.;Natori, S. Macromol Chem Phys 2006, 207, 1387–1393.
- 35 Natori, I.;Sato, H.;Natori, S. Polymer Int 2007, 56, 810–815.
- 36 Natori, I.;Natori, S. J.; Polym Sci Part A: Polym Chem 2008, 46, 3282–3293.
- 37 Natori, I.;Sato, H. J Polym Sci Part B: Polym Phys 2006, 44, 1442–1452.
