Structural modification of silicon-bridged ladder stilbene oligomers and distyrylbenzenes

Macromolecular Chemistry and Physics

Volumn 210, Issue 11, 2009, Pages 904-916

  Yamada, Hiroshi ^a   Xu, Caihong ^b   Fukazawa, Aiko ^a   Wakamiya, Atsushi ^a   Yamaguchi, Shigehiro ^a  

^a NAGOYA UNIVERSITY   (Japan)

^b INSTITUTE OF CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL CHAIN; CRYSTALLINE STATE; FLUORESCENCE QUANTUM YIELD; INTENSE EMISSION; NEIGHBORING MOLECULES; PACKING STRUCTURE; PHOTOPHYSICAL PROPERTIES; POTENTIAL EFFECTS; STRUCTURAL MODIFICATIONS;

ALKYLATION; CRYSTALLINE MATERIALS; OLIGOMERS; ORGANIC POLYMERS; X RAY CRYSTALLOGRAPHY;

SILICON COMPOUNDS;

EID: 67649771767     PISSN: 10221352     EISSN: 15213935     Source Type: Journal    
DOI: 10.1002/macp.200900037     Document Type: Article

References (65)

1. U. Scherf, J. Mater. Chem. 1999, 9, 1853;
2. M. D. Watson, A. Fechtenkötter, K. Müllen, Chem. Rev. 2001, 101, 1267;
3. J. E. Anthony, Chem. Rev. 2006, 106, 5028;
4. J. E. Anthony, Angew. Chem. 2008, 120, 460; Angew. Chem. Int. Ed. 2008, 47, 452.
5. P. Leclé re, M. Surin, P. Viville, R. Lazzaroni, A. F. M. Kilbinger, O. Henze, W. J. Feast, M. Cavallini, F. Biscarini, A. P. H. J. Schenning, E. W. Meijer, Chem. Mater. 2004, 16, 4452;
6. P. Leclé re, M. Surin, P. Brocorens, M. Cavallini, F. Biscarini, R. Lazzaroni, Mater. Sci. Eng. R 2006, 55, 1.
7. V. C. Sundar, J. Zaumseil, V. Podzorov, E. Menard, R. L. Willett, T. Someya, M. E. Gershenson, J. A. Rogers, Science 2004, 303, 1644.
8. Z. Xie, B. Yang, F. Li, G. Cheng, L. Liu, G. Yang, H. Xu, L. Ye, M. Hanif, S. Liu, D. Ma, Y. Ma, J. Am. Chem. Soc. 2005, 127, 14152.
9. T. Agou, J. Kobayashi, T. Kawashima, Org. Lett. 2006, 8, 2241;
10. T. Agou, J. Kobayashi, T. Kawashima, Chem. Commun. 2007, 3204;
11. T. Agou, J. Kobayashi, T. Kawashima, Chem. Eur. J. 2007, 13, 8051.
12. T. Matsuda, S. Kadowaki, T. Goya, M. Murakami, Org. Lett. 2007, 9, 133;
13. L. Li, J. Xiang, C. Xu, Org. Lett. 2007, 9, 4877;
14. M. Shimizu, K. Mochida, T. Hiyama, Angew. Chem. 2008, 120, 9906; Angew. Chem. Int. Ed. 2008, 47, 9760.
15. P. Kaszynski, D. A. Dougherty, J. Org. Chem. 1993, 58, 5209;
16. S. A. Patil, U. Scherf, A. Kadashchuk, Adv. Funct. Mater. 2003, 13, 609;
17. S. Wakim, J. Bouchard, N. Blouin, A. Michaud, M. Leclerc, Org. Lett. 2004, 6, 3413;
18. K. Kawaguchi, K. Nakano, K. Nozaki, J. Org. Chem. 2007, 72, 5119.
19. Y. Makioka, T. Hayashi, M. Tanaka, Chem. Lett. 2004, 33, 44;
20. H.-C. Su, O. Fadhel, C.-J. Yang, T.-Y. Cho, C. Fave, M. Hissler, C.-C. Wu, R. Re'au, J. Am. Chem. Soc. 2006, 128, 983;
21. T. Baumgartner, T. Neumann, B. Wirges, Angew. Chem. 2004, 116, 6323; Angew. Chem. Int. Ed. 2004, 43, 6197;
22. T. Baumgartner, W. Bergmans, T. Ka'rpa'ti, T. Neumann, M. Nieger, L. Nyula'szi, Chem. Eur. J. 2005, 11, 4687;
23. Y. Dienes, S. Durben, T. Ka'rpa'ti, T. Neumann, U. Englert, L. Nyula'szi, T. Baumgartner, Chem. Eur. J. 2007, 13, 7487.
24. A. Haryono, K. Miyatake, J. Natori, E. Tsuchida, Macromolecules 1999, 32, 3146;
25. H. Sirringhaus, R. H. Friend, C. Wang, J. Leuninger, K. Müllen, J. Mater. Chem. 1999, 9, 2095.
26. H. Sashida, S. Yasuike, J. Heterocycl. Chem. 1998, 35, 725;
27. K. Takimiya, Y. Kunugi, Y. Konda, H. Ebata, Y. Toyoshima, T. Otsubo, J. Am. Chem. Soc. 2006, 128, 3044;
28. K. Takimiya, H. Ebata, K. Sakamoto, T. Izawa, T. Otsubo, Y. Kunugi, J. Am. Chem. Soc. 2006, 128, 12604;
29. T. Yamamoto, K. Takimiya, J. Am. Chem. Soc. 2007, 129, 2224;
30. C.-H. Wang, R.-R. Hu, S. Liang, J.-H. Chen, Z. Yang, J. Pei, Tetrahedron Lett. 2005, 46, 4687;
31. K. T. Wong, T. C. Chao, L. C. Chi, Y. Y. Chu, A. Balaiah, S. F. Chiu, Y. H. Liu, Y. Wang, Org. Lett. 2006, 8, 5033.
32. S. Yamaguchi, C. Xu, T. Okamoto, Pure Appl. Chem. 2006, 78, 721.
33. S. Yamaguchi, C. Xu, K. Tamao, J. Am. Chem. Soc. 2003, 125, 13662;
34. C. Xu, H. Yamada, A. Wakamiya, S. Yamaguchi, K. Tamao, Macromolecules 2004, 37, 8978;
35. C. Xu, A. Wakamiya, S. Yamaguchi, J. Am. Chem. Soc. 2005, 127, 1638;
36. S. Yamaguchi, C. Xu, H. Yamada, A. Wakamiya, J. Organomet. Chem. 2005, 690, 5365.
37. A. Fukazawa, M. Hara, T. Okamoto, E.-C. Son, C. Xu, K. Tamao, S. Yamaguchi, Org. Lett. 2008, 10, 913.
38. A. Fukazawa, H. Yamada, S. Yamaguchi, Angew. Chem. 2008, 120, 5664; Angew. Chem. Int. Ed. 2008, 47, 5582.
39. K. Mouri, A. Wakamiya, H. Yamada, T. Kajiwara, S. Yamaguchi, Org. Lett. 2007, 9, 93.
40. K. Tamao, M. Uchida, T. Izumizawa, K. Furukawa, S. Yamaguchi, J. Am. Chem. Soc. 1996, 118, 11974;
41. M. Uchida, T. Izumizawa, T. Nakano, S. Yamaguchi, K. Tamao, K. Furukawa, Chem. Mater. 2001, 13, 2680.
42. C. Fave, T.-Y. Cho, M. Hissler, C.-W. Chen, T.-Y. Luh, C.-C. Wu, R. Re'au, J. Am. Chem. Soc. 2003, 125, 9254.
43. S. Destri, M. Pasini, C. Botta, W. Porzio, F. Bertini, L. Marchió , J. Mater. Chem. 2002, 12, 924;
44. M. Surin, P. Sonar, A. C. Grimsdale, K. Müllen, S. De Feyter, S. Habuchi, S. Sarzi, E. Braeken, A. V. Heyen, M. Van der Auweraer, F. C. De Schryver, M. Cavallini, J.-F. Moulin, F. Biscarini, C. Femoni, L. Roberto, P. Leclé re, J. Mater. Chem. 2007, 17, 728.
45. R. E. Martin, F. Diederich, Angew. Chem. 1999, 111, 1440; Angew. Chem. Int. Ed. 1999, 38, 1350.
46. T. A. Blinka, B. J. Helmer, R. West, Adv. Organomet. Chem. 1985, 23, 193.
47. S. Yamaguchi, T. M. Swager, J. Am. Chem. Soc. 2001, 123, 12087.
48. G. M. Sheldrick, SHELX-97, Program for the Refinement of Crystal Structures, University of Gottingen, Gottingen, Germany 1997.
49. Y. Kondo, M. Shilai, M. Uchiyama, T. Sakamoto, J. Am. Chem. Soc. 1999, 121, 3539.
50. Crystal data for 1, 2, 15, and 22: CCDC 715710 (1), 715711 (2), 715712 (15), and 715713 (22) contain supplementary crystallographic data for this paper. These data can be obtained free of charge from The Cambridge Crystallographic Data via www.ccdc.cam.ac.uk/data-request/cif.
51. B. Aldridge, G. De Luca, M. Edgar, S. J. Edgar, J. W. Emsley, M. I. C. Furby, M. Webster, Liq. Cryst. 1998, 24, 569.
52. Dendritic substitution protection approach: [26a] T. Sato, D.-L. Jiang, T. Aida, J. Am. Chem. Soc. 1999, 121, 10658;
53. J. M. Lupton, L. R. Hemingway, I. D. W. Samuel, P. L. Burn, J. Mater. Chem. 2000, 10, 867;
54. L.-O. Pa°lsson, R. Beavington, M. J. Frampton, J. M. Lupton, S. W. Magennis, J. P. J. Markham, J. N. G. Pillow, P. L. Burn, I. D. W. Samuel, Macromolecules 2002, 35, 7891;
55. Y.-H. Tseng, F.-I. Wu, P.-I. Shih, C.-F. Shu, J. Polym. Sci., Part A: Polym. Chem. 2005, 43, 5147;
56. T. Sanji, T. Kanzawa, M. Tanaka, J. Organomet. Chem. 2007, 692, 5053;
57. J. Wan, Y. Zhao, C. Dou, H. Sun, P. Xu, K. Ye, J. Zhang, S. Jiang, F. Li, Y. Wang, J. Phys. Chem. B 2007, 111, 5082; aggregate-induced emission:
58. J. Luo, Z. Xie, J. W. Y. Lam, L. Cheng, H. Chen, C. Qiu, H. S. Kwok, X. Zhan, Y. Liu, D. Zhu, B. Z. Tang, Chem. Commun. 2001, 1740;
59. H. Tong, Y. Dong, M. Häubler, J. W. Y. Lam, H. H.-Y. Sung, I. D. Williams, J. Sung, B. Z. Tang, Chem. Commun. 2006, 1133;
60. H. Tong, Y. Hong, Y. Dong, M. Häubler, J. W. Y. Lam, Z. Li, Z. Guo, Z. Guo, B. Z. Tang, Chem. Commun. 2006, 3705;
61. Y. Li, F. Li, H. Zhang, Z. Xie, W. Xie, H. Xu, B. Li, F. Shen, L. Ye, M. Hanif, D. Ma, Y. Ma, Chem. Commun. 2007, 231;
62. H. Tong, Y. Hong, Y. Dong, Y. Ren, M. Häussler, J. W. Y. Lam, K. S. Wong, B. Z. Tang, J. Phys. Chem. B 2007, 111, 2000; enhanced intramolecular charge transfer transition:
63. C.-H. Zhao, A. Wakamiya, Y. Inukai, S. Yamaguchi, J. Am. Chem. Soc. 2006, 128,15934;
64. A. Wakamiya, K. Mori, S. Yamaguchi, Angew. Chem. 2007, 119, 4351; Angew. Chem. Int. Ed. 2007, 46, 4273; J-aggregate formation:
65. T. E. Kaiser, H. Wang, V. Stepanenko, F. Würthner, Angew. Chem. 2007, 119, 5637; Angew. Chem. Int. Ed. 2007, 46, 5541.