Modulation of the aerobic oxidative polymerization in phenylazomethine dendrimers assembling copper complexes

Chemistry - A European Journal

Volumn 16, Issue 36, 2010, Pages 11003-11011

  Imaoka, Takane ^a   Kawana, Yuki ^b   Tsuji, Masahiro ^b   Yamamoto, Kimihisa ^a,b  

^a TOKYO INSTITUTE OF TECHNOLOGY   (Japan)

^b KEIO UNIVERSITY   (Japan)

Author keywords

Copper; Dendrimers; Oxidation; Polymerization poly(phenylene oxide)s

Indexed keywords

ATMOSPHERIC OXYGEN; COPPER CHLORIDES; COPPER COMPLEXES; DENDRIMER MOLECULES; ENGINEERING PLASTICS; EQUIMOLAR AMOUNT; GLASS TRANSITION TEMPERATURE; OXIDATIVE POLYMERIZATION; OXIDIZING REAGENTS; PHENOL DERIVATIVES; PHENYLAZOMETHINE DENDRIMERS; REACTION CONDITIONS; REACTION FIELDS; SCHIFF-BASE;

CATALYSTS; CHLORINE COMPOUNDS; COPPER; DENDRIMERS; FUNCTIONAL GROUPS; GLASS TRANSITION; OXIDATION; OXYGEN; PHENOLS; POLYMERIZATION; POLYPHENYLENE OXIDES;

COPPER COMPOUNDS;

EID: 77956978869     PISSN: 09476539     EISSN: 15213765     Source Type: Journal    
DOI: 10.1002/chem.201001516     Document Type: Article

References (79)

1. D. Aycock, V. Abolins, D. M. White, Encyclopedia of Polymer Science and Engineering, Vol. 13, Wiley-Interscience, New York, 1986, pp. 1-30.
2. A. S. Hay, J. Polym. Sci. Part A: Polym. Chem. 1998, 36, 505-517.
3. a) H Higashimura, K. Fujisawa, M. Kubota, S. Kobayashi, J Polym. Sci. Polym, Chem. Ed. 2005, 43, 1955-1962;
4. b) H. Higashimura, K. Fujisawa, Y. Moro-oka, M. Kubota, A. Shiga, A. Terahara, H. Uyama, S. Kobayashi, J. Am. Chem. Soc. 1998, 120, 8529-8530;
5. c) H. Higashimura, M. Kubota, A. Shiga, K. Fujisawa, Y. Moro-oka, H. Uyama, S. Kobayashi, Macromolecules 2000, 33, 1986-1995;
6. d) R. Ikeda, J. Sugihara, H. Uyama, S. Kobayashi, Macromolecules 1.996, 29, 8702-8705;
7. e) Y. Shibasaki, Y. Suzuki, M. Ueda, Macromolecules 2007, 40, 5322-5325.
8. A. S. Hay, H. S. Blanchard, G. F. Endres, J. W. Eustance, J. Am. Chem. Soc. 1959, 81, 6335-6336.
9. a) M. Kubo, Y. Itoh, M. Tsuji, N. Oda, H. Takeuchi, T. Itoh, Macromolecules 1998, 31, 3469-3472;
10. b) R. Ikeda, H. Tanaka, H. Uyama, S. Kobayashi, Macromolecules 2000, 33, 6648-6652.
11. K. Oyaizu, Y. Kumaki, K. Saito, E. Tsuchida, Macromolecules 2000, 33, 5766-5769.
12. K. Yamamoto, Y. Kawana, M. Tsuji, M. Hayashi, T. Imaoka,.J. Am. Chem. Soc. 2007, 129, 9256-9257.
13. a) J. W. J. Knapen, A. W. van der Made, J. C. de Wilde, P. W. N. M. van Leeuwen, P. Wijkens, D. M. Grove, G. van Koten, Nature 1994, 372, 659-663;
14. b) D. Astruc, F. Chardac, Chem. Rev. 2001, 101, 2991-3024;
15. c) R. van Heerbeek, P. C. Kamer, P. W. van Leeuwen, J. N. Reek, Chem, Rev. 2002, 102, 3717-3756;
16. d) D. Astruc, C. Ornelas, J. Ruiz, Acc, Chem. Res. 2008, 41, 841-856;
17. e) D. Astruc, E. Boisselier, C. Orneias, Chem. Rev. 2010, 110, 1857-1959.
18. a) R. M. Crooks, M. Zhao, L. Sun, V. Chechik, L. K. Yeung, Acc. Chem. Res. 2001, 34, 181-190;
19. b) I. Nakamula, Y. Yamanoi, T. Yonezawa, T. Imaoka, K. Yamamoto, H. Nishihara, Chem. Commun. 2008, 5716-5718;
20. c) K. Yamamoto, T. Imaoka, W. Chun, O. Enoki, H. Katoh, M. Takenaga, A. Sonoi, Nat. Chem. 2009, 1, 397-402;
21. d) N. Satoh, T. Nakashima, K. Kamikura, K. Yamamoto, Nat. Nanotechnol. 2008,.3, 106-111.
22. a) R. Breinbauer, E. N. Jacobsen, Angew. Chem. 2000, 112, 3750-3753;
23. Angew. Chem. Int. Ed. 2000, 39, 3604-3607;
24. b) C. Francavilla, M. D. Drake, F. V. Bright, M. R. Detty, J. Am. Chem. Soc. 2001, 123, 57-67;
25. c) A. Dahan, M, Portnoy, Chem. Commun. 2002, 2700-2701;
26. d) S. Gatard, S. Nlate, E. Cloutet, G. Bravie, J. C. Biais, D. Astruc, Angew. Chem. 2003, 115, 468-472;
27. Angew. Chem. Int. Ed. 2003, 42, 452-456;
28. e) A. Dahan, M. Portnoy, Org. Lett. 2003, 5, 1197-1200;
29. f) J. Zhang, H. Xu, Z. Dong, Y. Wang, J. Liu, J. Shen, J. Am. Chem. Soc. 2004, 126, 10556-10557;
30. g) E. Delort, T. Darbre, J. L. Reymond, J Am. Chem. Soc. 2004, 126, 15642-15643;
31. h) T. Fujihara, Y. Obora, M. Tokunaga, H. Sato, Y. Tsuji, Chem. Commun. 2005, 4526-4528;
32. i) A. Ouali, R. Laurent, A. M. Caminade, J. P. Majorai, M. Taillefer, J. Am. Chem. Soc. 2006, 128, 15990-15991;
33. j) B. Helms, J. M. J. Fréchet, Adv. Synth. Catal. 2006, 348, 1125-1148;
34. k) T. Fujihara, S. Yoshida, H. Ohta, Y. Tsuji, Angew. Chem. 2008, 120, 8434-8438;
35. Angew. Chem. Int. Ed. 2008, 47, 8310-8314.
36. K. Yamamoto, M. Higuchi, S. Shiki, M. Tsuruta, H. Chiba, Nature 2002, 415, 509-511.
37. K. Yamamoto, T. Imaoka, Bull. Chem. Soc. Jpn. 2006, 79, 511-526.
38. a) K. Albrecht, K. Yamamoto, J. Am. Chem. Soc. 2009, 131, 22442251;
39. b) J.-S. Cho, A. Kimoto, M. Higuchi, K. Yamamoto, Macromol. Chem. Phys. 2005, 206, 635-641.
40. K. Takanashi, H. Chiba, M. Higuchi, K. Yamamoto, Org. Lett. 2004, 6, 1709-1712.
41. a) T. Imaoka, R. Takana, K. Yamamoto, J. Polym. Sci. Polym. Chem. Ed. 2006, 44, 5229-5236;
42. b) T. Imaoka, H. Horiguchi, K. Yamamoto, J. Am. Chem. Soc. 2003, 125, 340-341.
43. a) L. Balogh, D. A. Tomalia, J. Am. Chem. Soc. 1998, 120, 7355-7356;
44. b) M. Zhao, L. Sun, R. M. Crooks, J. Am. Chem. Soc. 1998, 120, 4877-4878.
45. M. F. Ottaviani, F. Montalti, N. J. Turro, D. A. Tomalia, J. Phys. Chem. B 1997, 101,158-166.
46. M. F. Ottaviani, S. H. Bossmann, N. J. Turro, D. A, Tomalia, J Am. Chem. Soc. 1994, 116, 661-671.
47. a) M. Higuchi, S. Shiki, K. Ariga, K. Yamamoto, J Am. Chem. Soc. 2001, 125, 4414-4420;
48. b) T. Imaoka, R. Tanaka, K. Yamamoto, Chem. Eur. J. 2006, 12, 7328-7336.
49. a) M. Ballauff, C. N. Likos, Angew. Chem. 2004, 116, 3060-3082;
50. Angew. Chem. Int. Ed. 2004, 43, 2998-3020;
51. b) S. Rosenfeldt, N. Dingenouts, D. Pöschke, M. Ballauff, A. J. Berresheim, K. Müllen, P. Lindner, Angew. Chem. 2004, 116, 111-114;
52. Angew. Chem. Int. Ed. 2004, 43, 109-112.
53. a) D. Boris, M. Rubinstein, Macromolecules 1996, 29, 7251-7260;
54. b) M. Ballauff, Top. Curr. Chem. 2001, 212, 177-194;
55. c) M. Wind, K. Saalwähter, U. Wiesler, K. Müllen, H. W. Spiess, Macromolecules 2002, 55, 10071-10086.
56. a) M. Han, P. Chen, X. Yang, Polymer 2005, 46, 3481-3488;
57. b) P. K. Maiti, T. Çgin, G. Wang, W. A. Goddard III, Macromolecules 2004, 37, 6236-6254;
58. c) D. Pötschke, M, Ballauff, P. Lindner, M. Fischer, F. Vögtle, Macromolecules 1999, 32, 4079-4087;
59. d) M, Chai, Y. Niu, W. J. Youngs, P. L. Rinaldi, J. Am. Chem. Soc. 2001, 125, 4670-4678;
60. e) W. Ortiz, A. E. Roitberg, J. L. Krause, J. Phys. Chem. B 2004, 108, 8218-8225.
61. a) P. Gamez, P. G. Aubel, W. L. Driessen, J. Reedijk, Chem. Soc. Rev. 2001, 30, 376-385;
62. b) N. Kitajima, Y. Moro-oka, Chem. Rev. 1994, 94, 737-757;
63. c) W. B. Tolman., Acc. Chem. Res. 1997, 30, 227237;
64. d) E. A. Lewis, W. B. Tolman, Chem. Rev. 2004, 104, 10471076;
65. e) V. Mahadevan, J. L. DuBois, B. Hedman, K. O. Hodgson, T. D. P. Stack, J. Am. Chem. Soc. 1999, 121, 5583-5584;
66. f) S. Mahapatra, J. A. Halfen, W. B. Tolman, J Am. Chem. Soc. 1996, 118, 11575-11586.
67. 6) salts are safer electrolytes and are also available for these kinds of experiments.
68. E. Tsuchida, H. Nishide, T. Nishiyama, Makromol. Chem. 1975, 176, 1349-1.358.
69. S. H. Hyun, H. Nishide, E. Tsuchida, S. Yamada, Polym. Bull. 1988, 19, 527-532.
70. P. A. Chase, G. C. Welch, T. Jurca, D. W. Stephan, Angew. Chem. 2007, 119, 8196-8.199;
71. Angew. Chem. Int. Ed. 2007, 46, 8050-8053.
72. a)J. W. Labadie, J. L. Hedrick, Macromolecules 1990, 23, 53715373;
73. b) R. Singh, A. S. Hay, Macromolecules 1992, 25, 1017-1024.
74. W. S. Bahary, N. P. Hogan, M. Jilani, M. P. Aronson, Adv. Chem. Ser. 1995, 247, 151-166.
75. F.W. Billmeyer, Textbook of Polymer Science, 3rd ed., Wiley, New York, 1984, p. 208.
76. a) E. Tsuchida, K. Yamamoto, K. Oyaizu, F. Suzuki, A. S. Hay, Z. Y. Wang, Macromolecules 1995, 28, 409-416;
77. b) E. Tsuchida, F. Suzuki, E. Shouji, K. Yamamoto, Macromolecules 1994, 27, 1057-1060;
78. c) E. Tsuchida, H. Nishide, K. Yamamoto, S. Yoshida, Macromolecules 1987, 20, 2315-2316;
79. d) K. Yamamoto, E. Tsuchida, H. Nishide, M. Jikei, K. Oyaizu, Macromolecules 1993, 26, 3432-3437.