Crystal-lattice controlled photopolymerization of di(benzylammonium) (Z,Z)-muconates

Journal of the American Chemical Society

Volumn 121, Issue 48, 1999, Pages 11122-11129

  Matsumoto, Akikazu ^a   Odani, Toru ^a   Chikada, Masaaki ^b   Sada, Kazuki ^b   Miyata, Mikiji ^b  

^a Osaka Prefecture University   (Japan)

^b OSAKA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

AMMONIUM DERIVATIVE; MUCONIC ACID;

ARTICLE; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PHOTOCHEMISTRY; PHOTOREACTIVITY; POLYMERIZATION; REACTION ANALYSIS; X RAY ANALYSIS;

EID: 0033537025     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja992558g     Document Type: Article

References (57)

1. Schlüter, A.-Dieter, Ed. Synthesis of Polymers; Wiley-VCH: Weinheim, 1999.
2. (a) Otsu, T.; Matsumoto, A. Adv. Polym. Sci, 1998, 136, 75-137.
3. (b) Sawamoto, M.; Kamigaito, M. Synthesis of Polymers; Schlüter, A.-Dieter, Ed.; Wiley-VCH: Weinheim, 1999; pp 163-194.
4. (c) Matyjaszewski, K. ACS Symposium Series No. 685; American Chemical Society: Washington, DC, 1998.
5. (d) Moad, G.; Solomon, D. H. The Chemistry of Free Radical Polymerization; Pergamon: Oxford, 1995; pp 315-351.
6. (a) Paleos, M., Ed. Polymerization in Organized Media; Gordon and Breach: Philadelphia, 1992.
7. (b) Miyata, M. Comprehensive Supramolecular Chemistry; Reinhoudt, N. D., Ed.; Pergamon: Oxford, 1996; Vol. 10, pp 557-582.
8. (c) Stupp, S. I.; Osenar, P. Synthesis of Polymers; Schlüter, A.Dieter, Ed.; Wiley-VCH: Weinheim, 1999; pp 513-547.
9. (a) Okamoto, Y.; Nakano, T. Chem. Rev. 1994, 94, 349-372.
10. (b) Nakano, T.; Matsuda, A.; Okamoto, Y. Polym. J. 1996, 28, 556-558.
11. (c) Nakano, T.; Okamoto, Y. Macromolecules 1999, 32, 2391-2393.
12. Porter, N. A.; Allen, T. R.; Breyer, R. A. J. Am Chem. Soc. 1992, 114, 7676-7683.
13. (a) Miyata, M.; Kitahara, Y.; Takemoto, K. Polym. J. 1981, 13, 111-113.
14. (b) Farina, M.; Audisio, G.; Natta, G. J. Am. Chem. Soc. 1967, 89, 5071-5071.
15. (a) Schmidt, G. M. J. Pure Appl. Chem. 1971, 27, 647-678.
16. (b) Wegner, G. Pure Appl. Chem. 1977, 47, 443-454.
17. (c) Enkelmann, V. Adv. Polym. Sci. 1984, 63, 91-136.
18. (d) Hasegawa, M. Adv. Phys. Org. Chem. 1995, 30, 117-171.
19. (a) Matsumoto, A.; Matsumura, T.; Aoki, S. J. Chem. Soc., Chem. Commun. 1994, 1389-1390.
20. (b) Matsumoto, A.; Matsumura, T.; Aoki, S. Macromolecules 1996, 29, 423-432.
21. Matsumoto, A.; Yokoi, K.; Aoki, S.; Tashiro, K.; Kamae, T.; Kobayashi, M. Macromolecules 1998, 31, 2129-2136.
22. Tashiro, K.; Kamae, T.; Kobayashi, M.; Matsumoto, A.; Yokoi, K.; Aoki, S. Macromolecules 1999, 32, 2449-2454.
23. (a) Desiraju, G. R. Crystal Engineering: The Design of Organic Solids; Elsevier: Amsterdam, 1989.
24. (b) Zaworotko, M. J. Chem. Soc. Rev. 1994, 23, 283-288.
25. (c) Desiraju, G. R. Angew. Chem., Int. Ed. Engl. 1995, 34, 2311-2327.
26. (d) Lehn, J.-M. Supramolecular Chemistry; VCH: Weinheim, 1995.
27. (e) Comprehensive Supramolecular Chemistry; MacNicol, D. D., Toda, R, Bishop, R., Eds.; Pergamon: Oxford, 1996; Vol. 6.
28. (f) Hosseini, M. W.; DeCian, A. Chem. Commun. 1998, 727-733.
29. (g) Desiraju, G. R. Chem. Commun. 1997, 1475-1482.
30. (h) Nangia, A.; Desiraju, G. R. Top. Cur. Chem. 1998, 198, 57-95.
31. (a) Etter, M. C. Acc. Chem. Res. 1990, 23, 120-126.
32. (b) Aakeröy, C. B.; Seddon, K. R. Chem. Soc. Rev. 1993, 22, 397-407.
33. (c) MacDonald, J. C.; Whitesides, G. M. Chem. Rev. 1994, 94, 2383-2420.
34. (d) Meléndez, R. E.; Hamilton, A. D. Top. Cur. Chem. 1998, 198, 97-129.
35. (a) Aakeröy, C. B.; Hitchcock, P. B.; Seddon, K. R. J. Chem. Soc., Chem. Commun. 1992, 553-555.
36. (b) Aakeröy, C. B.; Nieuwenhuyzen, M. J. Am. Chem. Soc. 1994, 116, 10983-10991.
37. (a) Russell, V. A.; Etter, M. C.; Ward, M. D. J. Am. Chem. Soc. 1994, 116, 1941-1952.
38. (b) Russell, V. A.; Etter, M. C.; Ward, M. D. Chem. Mater. 1994, 6, 1206-1217.
39. (c) Russell, V. A.; Ward, M. D. Acta Crystallogr. 1996, B52, 209-214.
40. (d) Russell, V. A.; Ward, M. D. J. Mater. Chem. 1997, 7, 1123-1133.
41. (e) Russell, V. A.; Evans, C. C.; Li, W.; Ward, M. D. Science 1997, 276, 575-579.
42. (f) Swift, J. A.; Russell, V. A.; Ward, M. D. Adv. Mater. 1997, 9, 1183-1186.
43. (g) Swift, J. A.; Pivovar, A. M.; Reynolds, A. M.; Ward, M. D. J. Am. Chem. Soc. 1998, 120, 5887-5894.
44. (a) Melendez, R. E.; Sharma, C. V. K.; Zaworotko, M. J.; Bauer, C.; Rogers, R. D. Angew. Chem., Int. Ed. Engl. 1996, 35, 2213-2215.
45. (b) Sharma, C. V. K.; Bauer, C.; Rogers, R. D.; Zaworotko, M. J. Chem. Commun. 1997, 1559-1560.
46. (c) Biradha, K.; Dennis, D.; MacKinnon, V. A.; Zaworotko, M. J. J. Am. Chem. Soc. 1998, 120, 11894-11903.
47. (a) Sada, K.; Yoshikawa, K.; Miyata, M. Chem. Commun. 1998, 1763-1764.
48. (b) Sada, K.; Shiomi, N.; Miyata, M. J. Ain. Chem. Soc. 1998, 120, 10543-10544.
49. (a) Kinbara, K.; Hashimoto, Y.; Sukegawa, M.; Nohira, H.; Saigo, K. J. Am. Chem. Soc. 1996, 118, 3441-3449.
50. (b) Kinbara, K.; Sakai, K.; Hashimoto, Y.; Nohira, H.; Saigo, K. J. Chem. Soc., Perkin Trans. 2 1996, 2615-2622.
51. (c) Kinbara, K.; Kobayashi, Y.; Saiso, K. J. Chem. Soc., Perkin Trans. 2 1998, 1767-1775.
52. For example, see: Jacques, J.; Collet, A.; Wilen, S. H. Enantiomer, Racemates, and Resolutions: Krieger Publishing Co.: Malabar, FL, 1994.
53. For example: (a) Ito, Y.; Borecka, B.; Trotter, J.; Scheffer, J. R. Tetrahedron Lett. 1995, 36, 6083-6086.
54. (b) Ito, Y.; Borecka, B.; Olovsson, G.; Trotter, J.; Scheffer, J. R. Tetrahedron Lett. 1995, 36, 6087-6090.
55. (c) Kinbara, K.; Kai, A.; Maekawa, Y.; Hashimoto, Y.; Nanise, S.; Hasegawa, M.; Saigo, K. J. Chem. Soc., Perkin Trans. 2 1996, 247-253.
56. (d) Chenug, E.; Netherton, M. R.; Scheffer, J. R.; Trotter, J. J. Am. Chem. Soc. 1999, 121, 2919-2920.
57. Preliminary results for the polymerization of 1: Matsumoto, A.; Odani, T.; Aoki, S. Polym. J. 1998, 30, 358-360.