Cis-specific topochemical polymerization: Alternating copolymerization of 7,7,8,8-tetrakis(methoxycarbonyl)quinodimethane with 7,7,8,8- tetracyanoquinodimethane in the solid state

Angewandte Chemie - International Edition

Volumn 50, Issue 10, 2011, Pages 2253-2256

  Itoh, Takahito ^a   Suzuki, Tatsuya ^a   Uno, Takahiro ^a   Kubo, Masataka ^a   Tohnai, Norimitsu ^b   Miyata, Mikiji ^b  

^a MIE UNIVERSITY   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

Charge transfer complexes; Polymerization; Quinodimethane compounds; Topochemistry; X ray diffraction

Indexed keywords

ALTERNATING COPOLYMERIZATION; CHARGE TRANSFER COMPLEX; CHEMICAL EQUATIONS; CO-CRYSTALS; QUINODIMETHANE COMPOUNDS; QUINODIMETHANES; RADICAL MECHANISM; TETRACYANOQUINODIMETHANE; TETRAKIS; TITLE COMPOUNDS; TOPOCHEMICAL POLYMERIZATION; TOPOCHEMISTRY; UV IRRADIATION;

CHARGE TRANSFER; COPOLYMERS; DIFFRACTION; POLYMERS; SINGLE CRYSTALS; X RAY DIFFRACTION;

COPOLYMERIZATION;

EID: 79952065587     PISSN: 14337851     EISSN: 15213773     Source Type: Journal    
DOI: 10.1002/anie.201006928     Document Type: Article

References (63)

1. a) G. Wegner, Z. Naturforsch. B 1969, 24, 824;
2. b) G. Wegner, Pure Appl. Chem. 1977, 49, 443;
3. c) V. Enkelmann, Adv. Polym. Sci. 1984, 63, 91;
4. d) T. Ogawa, Prog. Polym. Sci. 1995, 20, 943;
5. e) G. W. Coates, A. R. Dunn, L. M. Henling, D. A. Dougherty, R. H. Grubbs, Angew. Chem. 1997, 109, 290;
6. Angew. Chem. Int. Ed. Engl. 1997, 36, 248;
7. f) D. J. Sandman, I. B. Kim, J. M. Njus, D. C. Lee, A. L. Cholli, S. Sahoo, Macromol. Symp. 2003, 192, 99;
8. g) D. J. Sandman, J. M. Njus, B. Tran, Macromol. Symp. 2004, 217, 77;
9. h) Y. H. Chan, J. T. Lin, I. W. P. Chen, C. H. Chen, J. Phys. Chem. B 2005, 109, 19161;
10. i) S. Dei, A. Matsumoto, A. Matsumoto, Macromolecules 2008, 41, 2467.
11. a) M. Hasegawa, Chem. Rev. 1983, 83, 507;
12. b) M. Hasegawa, Adv. Phys. Org. Chem. 1995, 30, 117;
13. c) G. W. Coates, A. R. Dunn, L. M. Henling, J. W. Ziller, E. B. Lobkovsky, R. H. Grubbs, J. Am. Chem. Soc. 1998, 120, 3641;
14. d) S. Takahashi, H. Miura, H. Kasai, S. Okada, H. Oikawa, H. Nakanishi, J. Am. Chem. Soc. 2002, 124, 10944;
15. e) D. Pestov, N. Levit, G. Tepper, Polymer 2003, 44, 3177;
16. f) N. Levit, O. Guney-Altay, D. Pestov, G. Tepper, Macromolecules 2005, 38, 6528.
17. a) J. Kiji, J. Kaiser, J. G. Wegner, R. C. Schulz, Polymer 1973, 14, 433;
18. b) V. Enkelmann, Chem. Mater. 1994, 6, 1337;
19. c) F. W. Fowler, J. W. Lauher, J. Phys. Org. Chem. 2000, 13, 850;
20. d) T. Hoang, J. W. Lauher, F. W. Fowler, J. Am. Chem. Soc. 2002, 124, 10656.
21. a) A. Matsumoto, T. Matsumura, S. Aoki, Macromolecules 1996, 29, 423;
22. b) A. Matsumoto, K. Yokoi, S. Aoki, K. Tashiro, T. Kamae, M. Kobayashi, Macromolecules 1998, 31, 2129;
23. c) A. Matsumoto, K. Sada, K. Tashiro, M. Miyata, T. Tsubouchi, T. Tanaka, T. Odani, S. Nagahama, T. Tanaka, K. Inoue, S. Saragai, S. Nakamoto, Angew. Chem. 2002, 114, 2612;
24. Angew. Chem. Int. Ed. 2002, 41, 2502;
25. d) A. Matsumoto, T. Tanaka, T. Tsubouchi, K. Tashiro, S. Saragai, S. Nakamoto, J. Am. Chem. Soc. 2002, 124, 8891;
26. e) A. Matsumoto, Polym. J. 2003, 35, 93;
27. f) S. Oshita, A. Matsumoto, Chem. Eur. J. 2006, 12, 2139;
28. g) D. Furukawa, A. Matsumoto, Macromolecules 2007, 40, 6048;
29. h) A. Matsumoto, D. Furukawa, Y. Mori, J. Tanaka, K. Oka, Cryst. Growth Des. 2007, 7, 1078;
30. i) T. Ueno, D. Furukawa, A. Matsumoto, Macromol. Chem. Phys. 2008, 209, 357.
31. a) T. Itoh, S. Nomura, T. Uno, M. Kubo, K. Sada, M. Miyata, Angew. Chem. 2002, 114, 4482;
32. Angew. Chem. Int. Ed. 2002, 41, 4306;
33. b) S. Nomura, T. Itoh, H. Nakasho, T. Uno, M. Kubo, K. Sada, K. Inoue, M. Miyata, J. Am. Chem. Soc. 2004, 126, 2035;
34. c) S. Nomura, T. Itoh, M. Ohtake, T. Uno, M. Kubo, A. Kajiwara, K. Sada, M. Miyata, Angew. Chem. 2003, 115, 5626;
35. Angew. Chem. Int. Ed. 2003, 42, 5468;
36. d) T. Itoh, S. Nomura, M. Ohtake, T. Yoshida, T. Uno, M. Kubo, A. Kajiwara, K. Sada, M. Miyata, Macromolecules 2004, 37, 8230;
37. e) T. Itoh, S. Yamashita, S. Nomura, T. Uno, M. Kubo, N. Tohnai, M. Miyata, Macromolecules 2009, 42, 6473.
38. a) C. L. Schauer, E. Maturey, F. W. Fowler, J. W. Lauher, J. Am. Chem. Soc. 1997, 119, 10245;
39. b) A. Matsumoto, T. Odani, M. Chikada, K. Sada, M. Miyata, J. Am. Chem. Soc. 1999, 48, 11122;
40. c) J. Xiao, M. Yang, J. W. Lauher, F. W. Fowler, Angew. Chem. 2000, 112, 2216;
41. Angew. Chem. Int. Ed. 2000, 39, 2132;
42. d) A. Matsumoto, K. Katayama, T. Odani, K. Oka, K. Tashiro, S. Saragai, S. Nakamoto, Macromolecules 2000, 33, 7786;
43. e) A. Matsumoto, S. Nagahama, T. Odani, J. Am. Chem. Soc. 2000, 122, 9109;
44. f) S. Nagahama, A. Matsumoto, J. Am. Chem. Soc. 2001, 123, 12176;
45. g) S. Nagahama, K. Inoue, K. Sada, M. Miyata, A. Matsumoto, Cryst. Growth Des. 2003, 3, 247;
46. h) R. Xu, V. Gramlich, H. Frauenrath, J. Am. Chem. Soc. 2006, 128, 5541;
47. i) A. Sun, J. W. Lauher, N. S. Goroff, Science 2006, 312, 1030;
48. j) L. Luo, C. Wilhelm, A. Sun, C. P. Grey, J. W. Lauher, N. S. Goroff, J. Am. Chem. Soc. 2008, 130, 7702;
49. k) J. W. Lauher, F. W. Fowler, N. S. Goroff, Acc. Chem. Res. 2008, 41, 1215;
50. l) R. Xu, B. Schweizer, H. Frauenrath, Chem. Eur. J. 2009, 15, 9105.
51. a) S. Iwatsuki, T. Itoh, Macromolecules 1980, 13, 983;
52. b) S. Iwatsuki, T. Itoh, I. Yokotani, Macromolecules 1983, 16, 1817;
53. c) S. Iwatsuki, T. Itoh, K. Horiuchi, Macromolecules 1978, 11, 497;
54. d) S. Iwatsuki, T. Itoh, I. Yokotani, Macromolecules 1979, 12, 208;
55. e) S. Iwatsuki, T. Itoh, Macromolecules 1982, 15, 347;
56. f) S. Iwatsuki, T. Itoh, Macromolecules 1983, 16, 1571;
57. g) T. Itoh, H. K. Hall, Jr., Macromolecules 1990, 23, 2836;
58. h) T. Itoh, Prog. Polym. Sci. 2001, 26, 1019.
59. int=0.279) reflections. The final R1 and wR2 values were 0.1377 [I>2.σs(I)] and 0.4058 (all data), respectively.
60. A. A. Bright, A. F. Garito, A. Heeger, Solid State Commun. 1973, 13, 943.
61. M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G. L. Cascarano, L. De Caro, C. Giacovazzo, G. Polidori, R. Spagna, J. Appl. Crystallogr. 2005, 38, 381.
62. CrystalStructure 3.8, Crystal Structure Analysis Package, Rigaku and Rigaku Americas (2000-2007): The Woodlands.
63. G. M. Sheldrick, SHELXL-97, Program for Crystal Structure Refinement, University of Göttingen (Germany), 1997.