Disubstituted liquid crystalline polyacetylene derivatives that exhibit linearly polarized blue and green emissions

Macromolecules

Volumn 44, Issue 16, 2011, Pages 6288-6302

  San Jose, Benedict A ^a   Matsushita, Satoshi ^a   Moroishi, Yasuyuki ^b   Akagi, Kazuo ^a  

^a KYOTO UNIVERSITY   (Japan)

^b UNIVERSITY OF TSUKUBA   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALIGNED FILMS; ALIGNMENT DIRECTION; ALKYL SPACERS; AROMATIC MOIETIES; CAST FILM; DICHROIC RATIOS; EMISSION COLOR; EXTERNAL FORCE; GREEN EMISSIONS; LINEAR DICHROISM; LINEARLY POLARIZED; LIQUID-CRYSTALLINE; LUMINESCENT MATERIAL; LYOTROPICS; MAIN CHAINS; MOLECULAR MOIETIES; POLYMER LAYERS; RUBBING TECHNIQUE; SIDE-CHAINS; XRD MEASUREMENTS;

ACETYLENE; ALIGNMENT; CRYSTALLINE MATERIALS; DICHROISM; ELECTROLUMINESCENCE; PHOTOLUMINESCENCE;

POLYMERS;

EID: 80051750890     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma201229g     Document Type: Article

References (84)

1. Naarrmann, H.; Theophilou, N. Synth. Met. 1987, 22, 1-8
2. Akagi, K.; Suezaki, M.; Shirakawa, H.; Kyotani, H.; Shimomura, M.; Tanabe, Y. Synth. Met. 1989, 28, D1-D10
3. Tsukamoto, J.; Takahashi, A.; Kawasaki, K. Jpn. J. Appl. Phys. 1990, 29, 125-130
4. Burroughes, J. H.; Bradley, D. C. C.; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend, R. H.; Burns, P. L.; Holmes, A. B. Nature 1990, 347, 539-541
5. Gustafsson, G.; Cao, Y.; Treacy, G. M.; Klavetter, F.; Colaneri, N.; Heeger, A. J. Nature 1992, 357, 477-479
6. Burn, P. L.; Holmes, A. B.; Kraft, A.; Bradley, D. C. C.; Brown, A. R.; Friend, R. H.; Gymer, R. W. Nature 1992, 356, 47-49
7. Grem, G.; Lditzky, G.; Ulrich, B.; Leising, G. Adv. Mater. 1992, 4, 36-37
8. Greenham, N. C.; Moratti, S. C.; Bradley, D. D. C.; Friend, R. H.; Holmes, A. B. Nature 1993, 365, 628-630
9. Kraft, A.; Grimsdale, A. C.; Holmes, A. B. Angew. Chem., Int. Ed. 1998, 37, 402-428
10. Katz, H. E.; Bao, Z.; Gilat, S. L. Acc. Chem. Res. 2001, 34, 359-369
11. Shacklette, L. W.; Eckhardt, H.; Chance, R. R.; Miller, G. G.; Ivory, D. M.; Baughman, R. H. J. Chem. Phys. 1980, 73, 4098-4102
12. McCullough, R. D.; Tristramnagle, S.; Williams, S. P.; Lowe, R. D.; Jayaraman, M. J. Am. Chem. Soc. 1993, 115, 4910-4911
13. Marks, R. N.; Halls, J. J. M.; Bradley, D. D. C.; Friend, R. H.; Holmes, A. B. J. Phys.: Condens. Matter 1994, 6, 1379-1394
14. Halls, J. J. M.; Walsh, C. A.; Greenham, N. C.; Marseglia, E. A.; Friend, R. H.; Moratti, S. C. Nature 1995, 376, 498-500
15. Tessler, N.; Denton, G. J.; Friend, R. H. Nature 1996, 382, 695-697
16. Sirringhaus, H.; Tessler, N.; Friend, R. H. Science 1998, 280, 1741-1744
17. Suga, T.; Konishi, H.; Nishide, H. Chem. Commun. 2007, 1730-1732
18. Sariciftci, N. S.; Braun, D.; Zhang, C.; Srdanov, V. I.; Heeger, A. J.; Stucky, G.; Wudl, F. Appl. Phys. Lett. 1993, 62, 585-587
19. Yu, G.; Heeger, A. J. Appl. Phys. 1995, 78, 4510-4515
20. Granstrom, M.; Petritsch, K.; Arias, A. C.; Lux, A.; Andersson, M. R.; Friend, R. H. Nature 1998, 395, 257-260
21. Daubler, T. K.; Glowacki, I.; Scherf, U.; Ulanski, J.; Horhold, H.-H.; Neher, D. J. Appl. Phys. 1999, 86, 6915-6923
22. Huynh, W. U.; Dittmer, J. J.; Alivisatos, A. P. Science 2002, 295, 2425-2427
23. Coakley, K. M.; McGehee, M. D. Chem. Mater. 2004, 16, 4533-4542
24. Trepka, W. J.; Sonnenfeld, R. J. J. Polym. Sci. 1970, 8, 2721-2724
25. Kern, R. J. J. Polym. Sci. 1969, 7, 621-631
26. Simionescu, C. I.; Percec, V. J. Polym. Sci., Polym. Symp. 1980, 67, 43-71
27. Oh, S. Y.; Akagi, K.; Shirakawa, H. Macromolecules 1993, 26, 6203-6206
28. Ting, C.-H.; Chen, J.-T.; Hsu, C.-S. Macromolecules 2002, 35, 1180-1189
29. Liu, K.-P.; Yu, Z.-Q.; Liu, J.-H.; Chen, E.-Q. Macromol. Chem. Phys. 2009, 210, 707-716
30. Koltzenburg, S.; Wolff, D.; Stelzer, F.; Springer, J.; Nuyken, O. Macromolecules 1998, 26, 9166-9173
31. Choi, S. K.; Gal, Y. S.; Jin, S. H.; Kim, H. K. Chem. Rev. 2000, 100, 1645-1682
32. Chen, Y.; Chen, L.; Zhou, W.; Zha, D.; Zhou, D.; Bai, F.; Wan, M. Synth. Met. 2009, 159, 1649-1656
33. Akagi, K.; Oguma, J.; Shirakawa, H. J. Photopolym. Sci. Technol. 1998, 11, 249-252
34. Akagi, K.; Oguma, J.; Shibata, S.; Toyoshima, R.; Osaka, I.; Shirakawa, H. Synth. Met. 1999, 102, 1287-1288
35. Oguma, J.; Kawamoto, R.; Goto, H.; Itoh, K.; Akagi, K. Synth. Met. 2001, 119, 537-538
36. Oguma, J.; Akagi, K.; Shirakawa, H. Synth. Met. 1999, 101, 86-87
37. Oguma, J.; Dai, X.-M.; Akagi, K. Mol. Cryst. Liq. Cryst. 2001, 365, 331-338
38. Suda, K.; Yoshida, J.; Nimori, S.; Akagi, K. Synth. Met. 2009, 159, 943-948
39. Akagi, K. Bull. Chem. Soc. Jpn. 2007, 80, 649-661
40. Akagi, K. Liquid Crystalline Conjugated Polymers Synthesis and Properties. In Thermotropic Liquid Crystals: Recent Advances; Ramamoorthy, A., Ed.; Springer: Dordrecht, The Netherlands, 2007; Chapter 9, pp 249-275.
41. Akagi, K.; Tanaka, H.; Toyoshima, R.; Shirakawa, H. Trans. Mater. Res. Soc. Jpn. 1994, 15A, 513
42. Toyoshima, R.; Narita, M.; Akagi, K.; Shirakawa, H. Synth. Met. 1995, 69, 289-290
43. Koide, N.; Iida, H. Mol. Cryst. Liq. Cryst. 1995, 261, 427-436
44. Toyoshima, R.; Akagi, K.; Shirakawa, H. Synth. Met. 1997, 84, 431-432
45. Akagi, K.; Narita, M.; Toyoshima, R.; Shirakawa, H. Mol. Cryst. Liq. Cryst. 1998, 318, 157-178
46. Akagi, K. Liquid Crystalline and Electroresponsive Polythiophenes. In Handbook of Thiophene-Based Materials: Applications in Organic Electronics and Photonics; Perepichka, I. F.; Perepichka, D. F., Eds.; John Wiley Sons: New York, 2009; Chapter 12, pp 497-515.
47. Vicentini, F.; Barrouillet, J.; Laversanne, R.; Mauzac, M.; Bibonne, F.; Parneix, J. P. Liq. Cryst. 1995, 19, 235-240
48. Ibison, P.; Foot, P. J. S.; Brown, W. Synth. Met. 1996, 76, 297-300
49. Osaka, I.; Shibata, S.; Toyoshima, R.; Akagi, K.; Shirakawa, H. Synth. Met. 1999, 102, 1437-1438
50. Osaka, I.; Goto, H.; Itoh, K.; Akagi, K. Synth. Met. 2001, 119, 541-542
51. Osaka, I.; Goto, H.; Itoh, K.; Akagi, K. Mol. Cryst. Liq. Cryst. 2001, 365, 339-346
52. Goto, H.; Itoh, K.; Akagi, K. Synth. Met. 2001, 119, 351-352
53. Goto, H.; Akagi, K. Macromolecules 2002, 35, 2545-2551
54. Shukla, A.; Mazumdar, S. Phys. Rev. Lett. 1999, 19, 3944-3947
55. Hidayat, R.; Fujii, A.; Ozaki, M.; Teraguchi, M.; Masuda, T.; Yoshino, K. Synth. Met. 2001, 119, 597-598
56. Shukla, A.; Ghosh, H.; Mazumdar, S. Synth. Met. 2001, 116, 87-90
57. Ghosh, H.; Shukla, A.; Mazumdar, S. Phys. Rev. B 2000, 19, 12763-12774
58. Vardeny, Z. V.; Korovyanko, O. In Handbook of Conducting Polymers, Conjugated Polymers, 3 rd ed.; Skotheim, T. A.; Reynolds, J. R., Eds.; CRC Press: New York, 2007; pp 22-1-22-74.
59. Lam, J. W. Y.; Tang, B. Z. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 2607
60. Liu, J.; Lam, J. W. Y.; Tang, B. Z. Chem. Rev. 2009, 109, 5799-5867
61. Yang, S.-H.; Huang, C.-H.; Chen, C.-H.; Hsu, C.-S. Macromol. Chem. Phys. 2009, 210, 37-47
62. Peng, H.; Chen, Y.; Chen, L.; He, X.; Li, F. J. Polym. Sci., Part A: Polym. Chem. 2010, 48, 5679-5692
63. Kwak, G.; Minakuchi, M.; Sakaguchi, T.; Masuda, T.; Fujiki, M. Chem. Mater. 2007, 19, 3654-3661
64. Kwak, G.; Fukao, S.; Fujiki, M.; Sakaguchi, T.; Masuda, T. Chem. Mater. 2006, 18, 5537-5542
65. Kwak, G.; Minakuchi, M.; Sakaguchi, T.; Masuda, T.; Fujiki, M. Macromolecules 2008, 41, 2743-2746
66. Lee, W-.E.; Kim, J-.W.; Oh, C-.J.; Sakaguchi, T.; Fujiki, M.; Kwak, G. Angew. Chem., Int. Ed. 2010, 49, 1406-1409
67. Iida, H.; Nakamura, A.; Inoue, Y.; Akagi, K. Synth. Met. 2003, 135, 91-92
68. Suda, K.; Akagi, K. J. Polym. Sci., Part A: Polym. Chem. 2008, 46, 3591-3610
69. Hayasaka, H.; Tamura, K.; Akagi, K. Macromolecules 2008, 41, 2341-2346
70. Hayasaka, H.; Miyashita, T.; Tamura, K.; Akagi, K. Adv. Funct. Mater. 2010, 20, 1243-1250
71. Akagi, K. J. Polym. Sci., Part A: Polym. Chem. 2009, 47, 2463-2485
72. Williamson, A. W. J. Chem. Soc. 1852, 4, 229-239
73. Sonogashira, K.; Tohda, Y.; Hagihara, N. Tetrahedron Lett. 1975, 16, 4467-4470
74. Sonogashira, K. J. Organomet. Chem. 2002, 653, 46-49
75. Miyaura, N.; Suzuki, A. J. Chem. Soc., Chem. Commun. 1979, 866-867
76. Miyaura, N.; Yamada, K.; Suzuki, A. Tetrahedron Lett. 1979, 20, 3437-40
77. Mitsunobu, O.; Yamada, M. Bull. Chem. Soc. Jpn. 1967, 40, 2380-2382
78. Liquid Crystalline and Mesomorphic Polymers; Shibaev, V. P.; Lam, L., Eds.; Springer-Verlag: New York, 1994.
79. Chien, J. C. W. Polymerization. In Polyacetylene: Chemistry, Physics, and Material Science; Academic Press: London, 1984; Chapter 2, pp 24-83.
80. Khotimsky, V. S.; Tchirkova, M. V.; Litvinova, E. G.; Rebrov, A. I.; Bordarenko, N. G. J. Polym. Sci., Polym. Chem. 2003, 41, 2133-2155
81. Masuda, T. J. Polym. Sci., Polym. Chem. 2007, 45, 165-180
82. Shibaev, V. P.; Plate, N. A. In Advances in Polymer Science; Gordon, M.; Plate, N. M., Eds.; Springer-Verlag: New York, 1984; Vol. 60, p 173.
83. Liquid Crystals: Experimental Study of Physical Properties and Phase Transitions; Kumar, S., Ed.; Cambridge University Press: Cambridge, 2001; pp 65-94.
84. Cheng, Y. J.; Luh, T. Y. Chem.-Eur. J. 2004, 10, 5361-5368