Synthesis of sulfonated polynaphthalene, polyanthracene, and polypyrene as strong solid acids via oxidative coupling polymerization

Journal of Applied Polymer Science

Volumn 127, Issue 6, 2013, Pages 4524-4536

  Tanemura, Kiyoshi ^a   Suzuki, Tsuneo ^a   Horaguchi, Takaaki ^b  

^a NIPPON DENTAL UNIVERSITY   (Japan)

^b NIIGATA UNIVERSITY   (Japan)

Author keywords

acid catalysts; oxidation; polymerization; solid acids; sulfonated polymers

Indexed keywords

ACID CATALYST; CHLOROSULFONIC ACID; CONDENSED POLYNUCLEAR AROMATICS; CYCLOHEXYL; OXIDATIVE COUPLING POLYMERIZATION; POLYANTHRACENE; SOLID ACID;

DICHLOROMETHANE; HYDROLYSIS; NAPHTHALENE; OXIDATION; POLYMERIZATION; RATE CONSTANTS;

VOLATILE FATTY ACIDS;

EID: 84871617062     PISSN: 00218995     EISSN: 10974628     Source Type: Journal    
DOI: 10.1002/app.38045     Document Type: Article

References (51)

1. Miyatake, K.,;, Shimura, T.,;, Mikami, T.,;, Watanabe, M., Chem. Commun. 2009, 42, 6403.
2. Miyatake, K.,;, Iyotani, H.,;, Yamamoto, K.,;, Tsuchida, E., Macromolecules 1996, 29, 6969.
3. Kobayashi, T.,;, Rikukawa, M.,;, Sanui, K.,;, Ogata, N., Solid State Ionics 1998, 106, 219.
4. Tago, T.,;, Kuwashiro, N.,;, Nishide, H., Bull. Chem. Soc. Jpn. 2007, 80, 1429.
5. Fujimoto, C. H.,;, Hickner, M. A.,;, Cornelius, C. J.,;, Loy, D. A., Macromolecules 2005, 38, 5010.
6. Granados-Focil, S.,;, Litt, M. H., Prepr. Pap. Am. Chem. Soc. Div. Fuel Chem. 2004, 49, 528.
7. Schuster, M.,;, de Araujo, C. C.,;, Atanasov, V.,;, Andersen, H. T.,;, Kreuer, K.-D.,;, Maier, J., Macromolecules 2009, 42, 3129.
8. Wang, L.,;, Xiang, S.,;, Zhu, G., Chem. Lett. 2009, 38, 1004.
9. Son, W.-K.,;, Kim, S. H.,;, Park, S.-G., Bull. Korean Chem. Soc. 2001, 22, 53.
10. Pang, J.,;, Wang, A.,;, Zheng, M.,;, Zhang, T., Chem. Commun. 2010, 46, 6935.
11. Toda, M.,;, Takagaki, A.,;, Okamura, M.,;, Kondo, J. N.,;, Hayashi, S.,;, Domen, K.,;, Hara, M., Nature 2005, 438, 178.
12. Mirkhani, V.,;, Moghadam, M.,;, Tangestaninejad, S.,;, Mohammadpoor-Baltork, I.,;, Mahdavi, M., Monatsh. Chem. 2009, 140, 1489.
13. Mo, X.,;, Lotero, E.,;, Lu, C.,;, Liu, Y.,;, Goodwin, J. G., Catal. Lett. 2008, 123, 1.
14. Liu, X.-Y.,;, Huang, M.,;, Ma, H.-L.,;, Zhang, Z.-Q.,;, Gao, J.-M.,;, Zhu, Y.-L.,;, Han, X.-J.,;, Guo, X.-Y., Molecules 2010, 15, 7188.
15. Okuhara, T,. Chem. Rev. 2002, 102, 3641.
16. Kamiya, Y.,;, Okuhara, T.,;, Misono, M.,;, Miyaji, A.,;, Ysuji, K.,;, Nakajo, T., Catal. Surv. Asia 2008, 12, 101.
17. Hara, M.,;, Yoshida, T.,;, Takagaki, A.,;, Takata, T.,;, Kondo, J. N.,;, Hayashi, S.,;, Domen, K., Angew. Chem. Int. Edn. 2004, 43, 2955.
18. Takagaki, A.,;, Toda, M.,;, Okamura, M.,;, Kondo, J. N.,;, Hayashi, S.,;, Domen, K.,;, Hara, M., Catal. Today 2006, 116, 157.
19. Tanemura, K.,;, Suzuki, T.,;, Nishida, Y.,;, Horaguchi, T., Tetrahedron 2011, 67, 1314.
20. Tanemura, K.,;, Suzuki, T.,;, Nishida, Y.,;, Horaguchi, T., Polym. Bull. 2012, 68, 705; DOI: 10.1007/s00289-011-0574-0.
21. Kovacic, P.,;, Jones, M. B., Chem. Rev. 1987, 87, 357.
22. Kovacic, P.,;, Kyriakis, A., J. Am. Chem. Soc. 1963, 85, 454.
23. Kovacic, P.,;, Oziomer, J., J. Org. Chem. 1964, 29, 100.
24. Yamamoto, K.,;, Asada, T.,;, Nishide, H.,;, Tsuchida, E., Bull. Chem. Soc. Jpn. 1988, 61, 1731.
25. King, B. T.,;, Kroulik, J.,;, Robertson, C. R.,;, Rempala, R.,;, Hilton, C. L.,;, Korinek, J. D.,;, Gortari, L. M., J. Org. Chem. 2007, 72, 2279.
26. Lu, Y.,;, Moore, H. S., Tetrahedron Lett. 2009, 50, 4071.
27. Matsumoto, K.,;, Ando, S.,;, Ueda, M., Polym. J. 2007, 39, 882.
28. Kovacic, P.,;, Koch, F. W., J. Org. Chem. 1965, 30, 3176.
29. Hara, S.,;, Toshima, N., Chem. Lett. 1990, 269.
30. Minato, H.,;, Higosaki, N.,;, Isobe, C., Bull. Chem. Soc. Jpn. 1969, 42, 779.
31. Ota, E.,;, Otani, S., Chem. Lett. 1975, 4, 241.
32. Ohsawa, T.,;, Nishihara, H.,;, Aramaki, K.,;, Takeda, S.,;, Yoshino, K., Polym. Commun. 1987, 28, 140.
33. Satoh, M.,;, Uesugi, F., Tabata, M.,;, Kaneto, K.,;, Yoshino, K. J., Chem. Soc. Chem. Commun. 1986, 1986, 979.
34. Drachev, A. I.,;, Gil'man, A. B.,;, Kuznetsov, A. A., High Energy Chem. (Engl. Transl.) 2005, 39, 418.
35. Berlin, A. A.,;, Grigorovskaya, V. A.,;, Parini, V. P.,;, Belova, G. V.,;, Chernikova, N. S., Vysokomol Sordin Ser. B 1967, 9, 423; Chem. Abstr. 1967, 67, 82422.
36. Buchanan, A. C., II, I, Dworkin, A. S.,;, Smith, G. P., J. Am. Chem. Soc. 1980, 102, 5262.
37. Dworkin, A. S.,;, Poustma, M. L.,;, Brynestad, J.,;, Brown, L. L.,;, Gilpatrick, L. O.,;, Smith. G. P., J. Am. Chem. Soc. 1979, 101, 5299.
38. Paustma, M. L.,;, Dworkin, A. S.,;, Brynestad, J.,;, Brown, L. L.,;, Benjamin, B. M.,;, Smith. G. P., Tetrahedron Lett. 1978, 19, 873.
39. Sato, H.,;, Aoyama, Y., Bull. Chem. Soc. Jpn. 1973, 46, 631.
40. Dworkin, A. S.,;, Brown, L. L.,;, Buchanan, A. C., III,;, Smith, G. P., Tetrahedron Lett. 1985, 23, 2727.
41. Buchanan, A. C., III,;, Dworkin, A. S.,;, Brown, L. L.,;, Smith, G. P., Prepr. Pap. Am. Chem. Soc. Div. Fuel Chem. 1981, 26, 112.
42. Fatiadi, A. J., J. Org. Chem. 1967, 32, 2903.
43. Clar, E.,;, Kühn, O., Justus Liebigs Ann. Chem. 1956, 601, 181.
44. Guenther, H.,;, Kovacic, P., Synth. Commun. 1984, 14, 413.
45. Packham, D. I., Chem. Commun. 1965, 1965, 207.
46. Li, X. G.,;, Liu, Y. W.,;, Huang, M. R.,;, Peng, S.,;, Gong, L. Z.,;, Moloney, M. G., Chem. Eur. J. 2010, 16, 4803.
47. Qu, L.,;, Shi, G., Chem. Commun. 2004, 2004, 2800.
48. Gharge, M. N.,;, Bhattar, S. L.,;, Kolekar, G. B.,;, Patil, S. R., Ind. J. Chem. 2008, 47A, 1642.
49. Sinha, N.,;, Gupta, M. K.,;, Goel, N.,;, Kumar, B., Phys. B 2011, 406, 3206.
50. Zong, M. H.,;, Duan, Z. Q.,;, Lou, W. Y.,;, Smith, T. J.,;, Wu, H., Green Chem. 2007, 9, 434.
51. Oguchi, T.,;, Limmatvapirat, S.,;, Takahashi, C.,;, Sungthongjeen, S.,;, Choi, W. S.,;, Yonemochi, E.,;, Yamamoto, K., Bull. Chem. Soc. Jpn. 1998, 71, 1573.