Functional polyacetylenes: Synthesis, thermal stability, liquid crystallinity, and light emission of polypropiolates

Macromolecules

Volumn 35, Issue 22, 2002, Pages 8288-8299

  Lam, Jacky W Y ^a   Luo, Jingdong ^a   Dong, Yuping ^a   Cheuk, Kevin K L ^a   Tang, Ben Zhong ^a  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Hong Kong)

Author keywords

[No Author keywords available]

Indexed keywords

QUANTUM YIELD;

CATALYSTS; DIFFERENTIAL SCANNING CALORIMETRY; ESTERIFICATION; GLASS TRANSITION; INFRARED SPECTROSCOPY; LIGHT EMISSION; LIQUID CRYSTAL POLYMERS; LUMINESCENCE; NUCLEAR MAGNETIC RESONANCE; POLYMERIZATION; SYNTHESIS (CHEMICAL); THERMODYNAMIC STABILITY; THERMOGRAVIMETRIC ANALYSIS; ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION;

POLYACETYLENES;

EID: 0037159263     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma021011a     Document Type: Article

References (130)

1. For recent reviews, see: (a) Shirakawa, H. Angew. Chem., Int. Ed. 2001, 40, 2575-2580.
2. (b) MacDiarmid, A.G. Angew. Chem., Int. Ed. 2001, 40, 2581-2590.
3. (c) Heeger, A.J. Angew. Chem., Int. Ed. 2001, 40, 2591-2611.
4. For selected reviews, see: (a) Masuda, T.; Higashimura, T. Adv. Polym. Sci. 1987, 81, 121.
5. (b) Gibson, H.W.; Pochan, J.M. In Concise Encyclopedia of Polymer Science and Engineering; Kroschwitz, J.I., Ed.; Wiley: New York, 1990; pp 7-9.
6. (c) Ginsburg, E.J.; Gorman, C.B.; Grubbs, R.H. In Modern Acetylene Chemistry; Stang, P.J., Diederich, F., Eds.; VCH: New York, 1995; Chapter 10, pp 353-383.
7. (d) Tabata, M.; Sone, T.; Sadahiro, Y. Macromol. Chem. Phys. 1999, 200, 265-282.
8. (e) Reddinger, J.L.; Reynolds, J.R. Adv. Polym. Sci. 1999, 145, 57-122.
9. (d) Volidal, J.; Sedlacek, J. In Chromatography of Polymers: Hyphenated and Multidimensional Techniques; Provder, T., Ed.; ACS Symposium Series 731; American Chemical Society: Washington, DC, 1999; Chapter 19, pp 263-287.
10. (a) Masuda, T.; Tang, B.Z.; Higashimura, T.; Yamaoka, H. Macromolecules 1985, 18, 2369-2373.
11. (b) Masuda, T.; Tang, B.Z.; Tanaka, T.; Higashimura, T. Macromolecules 1986, 19, 1459-1464.
12. (c) Seki, H.; Tang, B.Z.; Tanaka, A.; Masuda, T. Polymer 1994, 35, 3456-3462.
13. (d) Karim, S.M.; Nomura, R.; Masuda, T. J. Polym. Sci., Part A: Polym. Chem. 2001, 39, 3130-3136.
14. (a) Daranga, M.; Bulacovschi, V.; Mihailescu, C. Eur. Polym. J. 1990, 26, 117-120.
15. (b) Nishide, H.; Yoshioka, N.; Inagaki, K.; Kaku, T.; Tsuchida, E. Macromolecules 1992, 25, 569-575.
16. (c) Lee, H.J.; Shim, S.C. J. Chem. Soc., Chem. Commun. 1993, 1420-1422.
17. (d) Gal, Y.-S. J. Macromol. Sci., Pure Appl. Chem. 1994, A31, 703-714.
18. (d) Gal, Y.-S. J. Macromol. Sci., Pure Appl. Chem. 1994, A32, 61-72.
19. Masuda, T.; Kawai, M.; Higashimura, T. Polymer 1982, 23, 744-747.
20. (a) Ho, T.H.; Katz, T.J. J. Mol. Catal. 1985, 28, 359-367.
21. (b) Rossitto, F.C.; Lahti, P.M. Macromolecules 1993, 26, 6308-6309.
22. (a) Nishida, M.; Fujii, S.; Aoki, T.; Hayakama, Y.; Muramatsu, H.; Morita, T. J. Fluorine Chem. 1990, 46, 445-459.
23. (b) Tabata, M.; Tanaka, Y.; Sadahiro, Y.; Sone, T.; Yokota, K.; Miura, I. Macromolecules 1997, 30, 5200-5204.
24. (a) Katz, T.J.; Lee, S.J. J. Am. Chem. Soc. 1980, 102, 422-424.
25. (b) Gal, Y.-S.; Jung, B.; Lee, W.-C.; Choi, S.-K. J. Polym. Sci., Part A: Polym. Chem. 1992, 30, 2657-2662.
26. Calini, C.; Chien, J.C.W. J. Polym. Sci., Polym. Chem. Ed. 1984, 22, 2749-2766.
27. Gai, Y.-S. J. Chem. Soc., Chem. Commun. 1994, 327-328.
28. (a) Tang, B.Z.; Lam, J.W.Y.; Luo, J.D.; Dong, Y.; Cheuk, K.K.L.; Xie, Z.; Kwok, H.-S. In Liquid Crystals V; Khoo, I, Ed.; SPIE: Bellingham, WA, 2001; pp 132-138.
29. (b) Tang, B.Z.; Lam, J.W.Y.; Kong, X.; Salhi, F.; Cheuk, K.K.L.; Kwok, H.S.; Huang, Y.M.; Ge, W. In Liquid Crystals IV; Khoo, I., Ed.; SPIE: Bellingham, WA, 2000; pp 24-30.
30. (c) Tang, B.Z.; Lam, J.W.Y.; Kong, X.; Lee, P.P.S.; Wan, X.; Kwok, H.S.; Huang, Y.M.; Ge, W.; Chen, H.; Xu, R.; Wang, M. In Liquid Crystals III; Khoo, I., Ed.; SPIE: Bellingham, WA, 1999; pp 62-71.
31. (a) Lam, J.W.Y.; Dong, Y.P.; Cheuk, K.K.L.; Luo, J.D.; Xie, Z.L.; Kwok, H.S.; Mo, Z.S.; Tang, B.Z. Macromolecules 2002, 35, 1229-1240.
32. (b) Huang, Y.M.; Ge, W.; Lam, J.W.Y.; Cheuk, K.K.L.; Tang, B.Z. Mater. Sci. Eng., B 2001, 85, 242-246.
33. (c) Lam, J.W.Y.; Kong, X.; Dong, Y.P.; Cheuk, K.K.L.; Xu, K.; Tang, B.Z. Macromolecules 2000, 33, 5027-5040.
34. (d) Huang, Y.M.; Lam, J.W.Y.; Cheuk, K.K.L.; Ge, W.; Tang, B.Z. Thin Solid Films 2000, 363, 146-148.
35. (e) Huang, Y.M.; Ge, W.; Lam, J.W.Y.; Tang, B.Z. Appl. Phys. Lett. 1999, 75, 4094-4096.
36. (f) Huang, Y.; Bu, L.; Zhang, D.; Su, C.; Xu, Z.; Lam, J.W.Y.; Tang, B.Z. J. Funct. Polym. 1999, 12, 376-380.
37. (g) Kong, X.; Wan, X.; Kwok, H.S.; Feng, X.-D.; Tang, B.Z. Chin. J. Polym. Sci. 1998, 16, 185-192.
38. (a) Huang, Y.M.; Ge, W.; Lam, J.W.Y.; Tang, B.Z. Appl. Phys. Lett. 2001, 78, 1652-1654.
39. (b) Huang, Y.M.; Ge, W.; Lam, J.W.Y.; Cheuk, K.K.L.; Tang, B.Z. Mater. Sci. Eng., B 2001, 85, 122-125.
40. (c) Huang, Y.M.; Ge, W.; Lam, J.W.Y.; Cheuk, K.K.L.; Tang, B.Z. Mater. Sci. Eng., B 2001, 85, 118-121.
41. (d) Huang, Y.; Bu, L.J.; Bu, L.W.; Zhang, D.Z.; Su, C.W.; Xu, Z.D.; Lam, W.Y.; Tang, B.Z.; Mays, J.W. Polym. Bull. (Berlin) 2000, 44, 539-546.
42. (e) Huang, Y.M.; Lam, J.W.Y.; Cheuk, K.K.L.; Ge, W.; Tang, B.Z. Macromolecules 1999, 32, 5976-5978.
43. (f) Tang, B.Z.; Kong, X.; Feng, X.-D. Chin. J. Polym. Sci. 1999, 17, 289-294.
44. (g) Huang, M.Y.M.; Law, C.K.; Ge, W.; Lam, J.W.Y.; Tang, B.Z. J. Lamin. 2002, 99, 161-168.
45. (a) Tang, B.Z.; Chen, H.Z.; Xu, R.S.; Lam, J.W.Y.; Cheuk, K.K.L.; Wong, H.N.C.; Wang, M. Chem. Mater. 2000, 12, 213-221.
46. (b) Lee, P.P.S.; Geng, Y.H.; Kwok, H.S.; Tang, B.Z. Thin Solid Films 2000, 363, 149-151.
47. (c) Sun, J.Z.; Chen, H.Z.; Xu, R.S.; Wang, M.; Lam, J.W.Y.; Tang, B.Z. Chem. Commun. 2002, 1222-1223.
48. (a) Chen, H.Z.; Xu, R.S.; Sun, Q.H.; Lam, J.W.Y.; Wang, M.; Tang, B.Z. Polym. Adv. Technol. 2000, 11, 442-449.
49. (b) Tang, B.Z.; Poon, W.H.; Peng, H.; Wong, H.N.C.; Ye, X.; Monde, T. Chin. J. Polym. Sci. 1999, 17, 81-86.
50. (c) Yao, G.J.; Dong, Y.P.; Cae, T.B.; Yang, S.M.; Lam, J.W.Y.; Tang, B.Z. Chem. J. Chin. Univ. 2002, 23, 1202-1204.
51. (a) Tang, B.Z.; Kong, X.; Wan, X.; Feng, X.-D. Macromolecules 1998, 31, 7118.
52. (b) Tang, B.Z.; Kong, X.; Wan, X.; Feng, X.D. Macromolecules 1997, 30, 5620-5628.
53. (c) Kong, X.; Tang, B.Z. Chem. Mater. 1998, 10, 3352-3363.
54. (d) Tang, B.Z.; Kong, X.; Wan, X.; Peng, H.; Lam, W.Y.; Feng, X.; Kwok, H.S. Macromolecules 1998, 31, 2419-2432.
55. Xu, K.; Geng, Y.; Lee, P.P.S.; Tang, B.Z. Polym. Mater. Sci. Eng. 2000, 82, 103-104.
56. Xie, Z.; Lam, J.W.Y.; Luo, J.; Qiu, C.; Kwok, H.S.; Tang, B.Z. Polym. Prepr. 2001, 42 (2), 496-497.
57. (a) Xu, K.; Peng, H.; Lam, J.W.Y.; Peon, T.W.H.; Dong, Y.; Xu, H.; Sun, Q.; Cheuk, K.K.L.; Salhi, F.; Lee, P.P.S.; Tang, B.Z. Macromolecules 2000, 33, 6918-6924.
58. (b) Tang, B.Z.; Xu, K.; Sun, Q.; Lee, P.P.S.; Peng, H.; Salhi, F.; Dong, Y. ACS Symp. Ser. 2000, 760, 146-164.
59. (a) Mi, Y.; Tang, B.Z. Polym. News 2001, 26, 170-176.
60. (b) Lam, J.W.Y.; Luo, J.D.; Peng, H.; Xie, Z.L.; Xu, K.T.; Dong, Y.P.; Cheng, L.; Qiu, C.F.; Kwok, H.S.; Tang, B.Z. Chin. J. Polym. Sci. 2001, 19, 585-590.
61. (c) Tang, B.Z. Chem. Res. Chin. Univ. 2001, 17 (3), 59.
62. (a) Nakako, H.; Nomura, R.; Masuda, T. Macromolecules 2001, 34, 1496-1502.
63. (b) Maeda, K.; Goto, H.; Yashima, E. Macromolecules 2001, 34, 1160-1164.
64. (c) Nakako, H.; Mayahara, Y.; Nomura, R.; Tabata, M.; Masuda, T. Macromolecules 2000, 33, 3978-3982.
65. (d) Nomura, R.; Fukushima, Y.; Nakako, H.; Masida, T. J. Am. Chem. Soc. 2000, 122, 8830-8836.
66. (e) Nakako, H.; Nomura, R.; Tabata, M.; Masuda, T. Macromolecules 1999, 32, 2861-2864.
67. Tabata, M.; Inaba, Y.; Yokota, K.; Nozaki, Y. J. Macromol. Sci., Pure Appl. Chem. 1994, A31, 465-475.
68. For reviews, see: (a) Shirakawa, H.; Masuda, T.; Takeda, K. In The Chemistry of Triple-Bonded Functional Groups; Patai, S., Ed.; Wiley: New York, 1994; Suppl. C2, Chapter 17, pp 945-1016.
69. (b) Nakano, T.; Okamoto, Y. Chem. Rev. 2001, 101, 4013-4038.
70. (c) Yashima, E. Anal. Sci. 2002, 18, 3-6.
71. (a) Tang, B.Z. Polym. News 2001, 26, 262-272.
72. (b) Tang, B.Z.; Cheuk, K.K.L.; Salhi, F.; Li, B.S.; Lam, J.W.Y.; Cha, J.A.K.; Xiao, X.D. ACS Symp. Ser. 2001, 812, 133-148.
73. Kong, X.; Lam, J.W.Y.; Tang, B.Z. Macromolecules 1999, 32, 1722-1730.
74. (a) Imire, C.T.; Schleeh, T.; Karasz, F.E.; Attard, G.S. Macromolecules 1993, 26, 539.
75. (b) Imire, C.T.; Karasz, F.E.; Attard, G.S. Macromolecules 1993, 26, 545.
76. (a) Handbook of Liquid Crystal Research; Coilings, P.J., Patel, J.S., Eds.; Oxford University Press: New York, 1997.
77. (b) Cowie, J.M.G. Polymers: Chemistry & Physics of Modern Materials, 2nd ed.; Blackie: London, 1997; Chapter 16.
78. (c) McArdle, C.B. Side Chain Liquid Crystal Polymers; Blackie: London, 1989.
79. (a) Masuda, T.; Yoshimura, T.; Tamura, Y.; Higashimura, T. Macromolecules 1987, 20, 1734-1739.
80. (b) Masuda, T.; Yamagata, M.; Higashimura, T. Macromolecules 1984, 17, 126-129.
81. Tang, B.Z.; Kotera, N. Macromolecules 1989, 22, 4388-4390.
82. Silverstein, R.M.; Webster, F.X. Spectrometric Identification of Organic Compounds, 6th ed.; Wiley: New York, 1998.
83. Carey, F.A. Organic Chemistry, 3rd ed.; McGraw-Hill: New York, 1996; Chapter 10.
84. Lambert, J.B. Shurvell, H.F.; Lightner, D.A.; Cooks, R.G. Organic Structural Spectroscopy; Prentice Hall: Upper Saddle River, NJ, 1998; Chapter 3.
85. (a) Percec, V. Pugh, C. In Side Chain Liquid Crystal Polymers; McArdle, C.B., Ed.; Chapman & Hall: New York, 1989; Chapter 3, pp 30-105.
86. (b) Liquid Crystalline Polymer Systems; Isayev, A.I., Kyu, T., Cheng, S.Z.D., Eds.; American Chemical Society: Washington, DC, 1996.
87. (c) Pugh, C.; Kiste, A.L. Prog. Polym. Sci. 1997, 22, 601-691.
88. (d) Shiota, A.; Ober, C.K. Prog. Polym. Sci. 1997, 22, 975-1000.
89. Cowie, J.M.G. Polymers: Chemistry and Physics of Modern Materials, 2nd ed; Blackie: New York, 1991.
90. g. It is difficult, if not impossible, to separate these two transitions because the glass transitions are inherently associated with the melting transitions in our polyacetylene systems.
91. Note that the DSC thermogram of the polymer was measured during the first cooling scan. The thermal transitions here were thus for a sample that had already been partially isomerized during the first heating scan.
92. The sample was not heated to the isotropization point but not to the isomerization temperature.
93. 16b.
94. Liquid Crystalline Order in Polymers; Blumstein, A., Hsu, E.C., Eds.; Academic Press: New York, 1978.
95. Liu, Z.; Zhu, L.; Zhou, W.; Cheng, S.Z.D.; Percec, V.; Ungar, G. Chem. Mater. 2002, 14, 2384-2392 and references therein.
96. 1H NMR spectra (not shown).
97. (b) Molecular weights of substituted polyacetylenes had little effects on their absorption spectra: Dong, Y.; Lam, J.W.Y.; Cha, J.A.K.; Tang, B.Z. Polym. Mater. Sci. Eng. 2001, 84, 539-540.
98. -1, respectively. (a) Silverstein, R.M.; Bassler, G.C.; Morrill, T.C. Spectrometric Identification of Organic Compounds, 5th ed.; Wiley: New Youk, 1991; Chapter 7. (b) Pretsch, E.; Buhlmann, P.; Affolter, C. Structure Determination of Organic Compounds: Table of Spectral Data, 3rd ed.; Springer: Hong Kong, 2000; Chapter 8.
99. -1, respectively. (a) Silverstein, R.M.; Bassler, G.C.; Morrill, T.C. Spectrometric Identification of Organic Compounds, 5th ed.; Wiley: New Youk, 1991; Chapter 7. (b) Pretsch, E.; Buhlmann, P.; Affolter, C. Structure Determination of Organic Compounds: Table of Spectral Data, 3rd ed.; Springer: Hong Kong, 2000; Chapter 8.
100. (a) Luo, J.D.; Xie, Z.L.; Lam, J.W.Y.; Cheng, L.; Chen, H.Y.; Qiu, C.F.; Kwok, H.S.; Zhan, X.W.; Liu, Y.Q.; Zhu, D.B.; Tang, B.Z. Chem. Commun. 2001, 1740-1741.
101. (b) Tang, B.Z.; Zhan, X.; Yu, G.; Lee, P.P.S.; Liu, Y.Q.; Zhu, D.B.J. Mater. Chem. 2001, 11, 2874-2978.
102. (c) Freemantle, M. Chem. Eng. News 2001, 79 (1), 29.
103. (d) Chen, H.Y.; Lam, J.W.Y.; Luo, J.D.; Ho, Y.L.; Tang, B.Z.; Zhu, D.B.; Wong, M.; Kwok, H.S. Appl. Phys. Lett. 2002, 81, 574-576.
104. (a) Kim, J.; Swager, T.M. Nature (London) 2001, 411, 1030-1034.
105. (b) de Boer, B.; Stalmach, U.; van Hutten, P.F.; Melzer, C.; Krasnikov, V.V.; Hadziioannou, G. Polymer 2001, 42, 9097-9109.
106. (c) Wang, Y.Z.; Gebler, D.D.; Fu, D.K.; Swager, T.M.; MacDiarmid, A.G.; Epstein, A.J. Synth. Met. 1997, 85, 1179-1182.
107. (a) Hidayat, R.; Tatsuhara, S.; Kim, D.W.; Ozaki, M.; Yoshino, K.; Teraguchi, M.; Masuda, T. Phys. Rev. B 2000, 61, 10167.
108. (b) Frolov, S.V.; Fujii, A.; Chinn, D.; Hirohata, M.; Hidayat, R.; Taraguchi, M.; Masuda, T.; Yoshino, K.; Vardeny, Z.V. Adv. Mater. 1998, 10, 869.
109. (a) Sun, R.G. Zheng, Q.B.; Zhang, X.M.; Masuda, T.; Kobayashi, T. Jpn. J. Appl. Phys. 1999, 38, 2017.
110. (b) Sun, R.G.; Masuda, T.; Kobayashi, T. Synth. Met. 1997, 91, 301.
111. (a) Friend, R.H.; Gymer, R.W.; Holmes, A.B.; Burroughes, J.H.; Marks, R.N.; Taliani, C.; Bradley, D.D.C.; Dos Santos, D.A.; Bredas, J.L.; Logdlund, M.; Salaneck, W.R. Nature (London) 1999, 397, 121-128.
112. (b) Li, X.-C.; Moratti, S.C. In Photonic Polymer Systems: Fundamentals, Methods, and Applications; Wise, D.L., Wnek, G.E., Trantolo, D.J., Cooper, T.M., Gresser, J.D., Eds.; Marcel Dekker: Hong Kong, 1998; Chapter 10, pp 335-371.
113. (c) Heeger, A.J.; Diaz-Garcia, M.A. Curr. Opin. Solid State Mater. Sci. 1998, 3, 16-22.
114. Son, S.; Dodabalapur, A.; Lovinger, A.J.; Galvin, M.E. Science 1995, 269, 376-378.
115. (a) Xie, Z.L.; Lam, J.W.Y.; Chen, J.W.; Dong, Y.P.; Qiu, C.F.; Wong, M.; Kwok, H.S.; Tang, B.Z. Polym. Prepr. 2002, 43 (1), 411-412.
116. (b) Xie, Z.L.; Lam, J.W.Y.; Chen, J.W.; Dong, Y.P.; Qiu, C.F.; Wong, M.; Kwok, H.S.; Tang, B.Z. Polym. Prepr. 2002, 43 (1), 551-552.
117. (c) Xie, Z.L.; Lam, J.W.Y.; Chert, J.W.; Dong, Y.P.; Qiu, C.F.; Kwok, H.S.; Tang, B.Z. Polym. Mater. Sci. Eng. 2002, 86, 185-186.
118. (d) Lam, J.W.Y.; Xie, Z.L.; Chen, J.W.; Dong, Y.P.; Qiu, C.F.; Kwok, H.S.; Tang, B.Z. Polym. Mater. Sci. Eng. 2002, 86, 231-232.
119. (a) Xie, Z.L.; Lam, J.W.Y.; Qiu, C.F.; Luo, J.D.; Tang, B.Z.; Kwok, H.S. Asia Display/IDW 2001, 1451-1453.
120. (b) Xie, Z.; Lam, J.W.Y.; Luo, J.; Qiu, C.; Kwok, H.S.; Tang, B.Z. Polym. Prepr. 2001, 42 (2), 496-497.
121. (c) Dong, Y.; Lam, J.W.Y.; Lee, P.P.S.; Tang, B.Z. Polym. Mater. Sci. Eng. 2001, 84, 639-640.
122. (d) Dong, Y.P.; Lam, J.W.Y.; Tang, B.Z. Polym. Mater. Sci. Eng. 2001, 84, 616-617.
123. (e) Dong, Y.P.; Lam, J.W.Y.; Cha, J.A.K.; Tang, B.Z. Polym. Mater. Sci. Eng. 2001, 84, 539-540.
124. Zhou, Q.F.; Wan, X.H.; Zhang, D.; Feng, X.D. ACS Symp. Ser. 1996, 632, 344-357.
125. E.g.: (a) Schenning, A.P.H.J.; Fransen, M.; Meijer, E.W. Macromol. Rapid Commun. 2002, 23, 266-270.
126. (b) Ting, C.H.; Chen, J.T.; Hsu, C.S. Macromolecules 2002, 35, 1180-1189.
127. (c) Kuroda, H.; Goto, H.; Akagi, K.; Kawaguchi, A. Macromolecules 2002, 35, 1307-1313.
128. (d) Stagnaro, P.; Cavazza, B.; Trefiletti, V.; Costa, G.; Gallot, B.; Valenti, B. Macromol. Chem. Phys. 2001, 202, 2065-2073.
129. (e) Koltzenburg, S.; Wolff, D.; Stelzer, F.; Springer, J.; Nuyken, O. Macromolecules 1998, 31, 9166-9173.
130. Tang, B.Z.; Poon, W.H.; Leung, S.M.; Leung, W.H.; Peng, H. Macromolecules 1997, 30, 2209-2212.