Synthesis, mesomorphism, isomerization, and aromatization of stereoregular poly{[4-({[6-({[4′-(heptyl) oxy-4-biphenylyl]carbonyl}oxy)-hexyl]oxy}carbonyl) phenyl]acetylene}

Macromolecules

Volumn 32, Issue 6, 1999, Pages 1722-1730

  Kong, Xiangxing ^a   Lam, Jacky Wing Yip ^a   Tang, Ben Zhong ^a  

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

Author keywords

[No Author keywords available]

Indexed keywords

AROMATIZATION; CONFORMATIONS; DIFFERENTIAL SCANNING CALORIMETRY; INFRARED SPECTROSCOPY; ISOMERIZATION; LIQUID CRYSTALS; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; SYNTHESIS (CHEMICAL); ULTRAVIOLET SPECTROSCOPY; X RAY DIFFRACTION ANALYSIS;

CHAIN SCISSION; INTRACHAIN CYCLIZATION; MESOMORPHISM;

ORGANIC POLYMERS;

EID: 13044311382     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma981370z     Document Type: Article

References (96)

1. For reviews, see: (a) Handbook of Conducting Polymers, 2nd ed.; Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998. (b) Ginsburg, E. J.; Gorman, C. B.; Grubbs, R. H. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: New York, 1995; p 353. (c) Shirakawa, H.; Masuda, T.; Takeda, K. In The Chemistry of Triple-Bonded Functional Groups, Supplement C2; Patai, S., Ed.; Wiley: New York, 1994; Chapter 17. (d) Schrock, R. R. Acc. Chem. Res. 1990, 23, 158. (e) Masuda, T.; Higashimura, T. Adv. Polym. Sci. 1987, 81, 121.
2. For reviews, see: (a) Handbook of Conducting Polymers, 2nd ed.; Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998. (b) Ginsburg, E. J.; Gorman, C. B.; Grubbs, R. H. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: New York, 1995; p 353. (c) Shirakawa, H.; Masuda, T.; Takeda, K. In The Chemistry of Triple-Bonded Functional Groups, Supplement C2; Patai, S., Ed.; Wiley: New York, 1994; Chapter 17. (d) Schrock, R. R. Acc. Chem. Res. 1990, 23, 158. (e) Masuda, T.; Higashimura, T. Adv. Polym. Sci. 1987, 81, 121.
3. For reviews, see: (a) Handbook of Conducting Polymers, 2nd ed.; Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998. (b) Ginsburg, E. J.; Gorman, C. B.; Grubbs, R. H. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: New York, 1995; p 353. (c) Shirakawa, H.; Masuda, T.; Takeda, K. In The Chemistry of Triple-Bonded Functional Groups, Supplement C2; Patai, S., Ed.; Wiley: New York, 1994; Chapter 17. (d) Schrock, R. R. Acc. Chem. Res. 1990, 23, 158. (e) Masuda, T.; Higashimura, T. Adv. Polym. Sci. 1987, 81, 121.
4. For reviews, see: (a) Handbook of Conducting Polymers, 2nd ed.; Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998. (b) Ginsburg, E. J.; Gorman, C. B.; Grubbs, R. H. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: New York, 1995; p 353. (c) Shirakawa, H.; Masuda, T.; Takeda, K. In The Chemistry of Triple-Bonded Functional Groups, Supplement C2; Patai, S., Ed.; Wiley: New York, 1994; Chapter 17. (d) Schrock, R. R. Acc. Chem. Res. 1990, 23, 158. (e) Masuda, T.; Higashimura, T. Adv. Polym. Sci. 1987, 81, 121.
5. For reviews, see: (a) Handbook of Conducting Polymers, 2nd ed.; Skotheim, T. A., Elsenbaumer, R. L., Reynolds, J. R., Eds.; Marcel Dekker: New York, 1998. (b) Ginsburg, E. J.; Gorman, C. B.; Grubbs, R. H. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: New York, 1995; p 353. (c) Shirakawa, H.; Masuda, T.; Takeda, K. In The Chemistry of Triple-Bonded Functional Groups, Supplement C2; Patai, S., Ed.; Wiley: New York, 1994; Chapter 17. (d) Schrock, R. R. Acc. Chem. Res. 1990, 23, 158. (e) Masuda, T.; Higashimura, T. Adv. Polym. Sci. 1987, 81, 121.
6. Tang, B. Z.; Kong, X.; Wan, X.; Feng, X.-D. Macromolecules 1997, 30, 5620.
7. (b) Tang, B. Z.; Kong, X.; Wan, X.; Feng, X.-D. Macromolecules 1998, 31, 7118.
8. (c) Kong, X.; Wan, X.; Kwok, H. S.; Feng, X.-D.; Tang, B. Z. Chin. J. Polym. Sci. 1998, 16, 185.
9. (d) Tang, B. Z.; Poon, W. H.; Leunng, S. M.; Leung, W. H.; Peng, H. Macromolecules 1997, 30, 2209.
10. (e) Kong, X.; Wan, X.; Feng, X.-D.; Tang, B. Z. Polym. Mater. Sci. Eng. 1997, 77, 517.
11. (f) Tang, B. Z.; Poon, W. H.; Leunng, S. M.; Leung, W. H.; Peng, H. Polym. Mater. Sci. Eng. 1997, 77, 513.
12. Tabata, M.; Tanaka, Y.; Sadahiro, Y.; Sone, T.; Yokota, K.; Miura, I. Macromolecules 1997, 30, 5200.
13. (b) Furlani, A.; Napoletano, C.; Russo, M. U.; Camus, A.; Margich, N. J. Polym. Sci., Polym. Chem. 1989, 27, 75.
14. (c) Furlani, A.; Licoccia, S.; Russo, M. V. J. Polym. Sci., Part A: Polym. Chem. 1986, 24, 991.
15. (d) Schrock, R. R.; Luo, S.; Lee, J. C.; Zanetti, N. C.; Davis, W. M. J. Am. Chem. Soc. 1996, 118, 3883.
16. (e) Schrock, R. R.; Luo, S.; Zanetti, N. C.; Fox, H. H. Organometallics 1994, 13, 3396.
17. (f) Rossitto, F. C.; Lahti, P. M. Macromolecules 1993, 26, 6308.
18. (g) Nishide, H.; Yoshioka, N.; Inagaki, K.; Kaku, T.; Tsuchida, E. Macromolecules 1992, 25, 569.
19. (h) Fujii, A.; Ishida, T.; Koga, N.; Iwamura, H. Macromolecules 1991, 24, 1077.
20. (i) Iwamura, H.; McKelvey, R. D. Macromolecules 1988, 21, 3386.
21. Mylnikov, V. Adv. Polym. Sci. 1994, 115, 1.
22. (b) Zhao, J.; Yang, M.; Shen, Z. Polym. J. 1991, 23, 963.
23. (c) Kang, E. T.; Neoh, K.; Masuda, T.; Higashimura, T.; Yamamoto, M. Polymer 1989, 30, 1328.
24. (d) Kang, E. T.; Ehrlich, P.; Bhatt, A. P.; Anderson, W. A. Macromolecules 1984, 17, 1020.
25. (e) The polymer reported in this paper has been found to show photoconductivity in the whole visible spectral region upon doping by crystal violet, with the best results obtained at 573 nm: Xu, R.; Chen, H.; Wang, M.; Feng, L.; Lam, J. W. L.; Tang, B. Z., manuscript in preparation.
26. Le Moigne, J.; Hiberer, A.; Strazielle, C. Macromolecules 1992, 25, 6705.
27. (b) Prasad, P. N.; Williams, D. J. In Indroduction to Nonlinear Optical Effects in Molecules and Polymers; Wiley: New York, 1991; Chapter 10.
28. (c) Prasad, P. N. Solid Thin Films 1987, 152, 275.
29. We have found that the cis content of a stereoregular poly-(phenylacetylene) dramatically changes its photoluminescence efficiency. See: (a) Wong, K. S.; Lee, C. W.; Tang, B. Z. Synth. Met., in press. (b) Lee, C. W.; Wong, K. S.; Lam, W. Y.; Tang, B. Z. Chem. Phys. Lett., submitted for publication.
30. We have found that the cis content of a stereoregular poly-(phenylacetylene) dramatically changes its photoluminescence efficiency. See: (a) Wong, K. S.; Lee, C. W.; Tang, B. Z. Synth. Met., in press. (b) Lee, C. W.; Wong, K. S.; Lam, W. Y.; Tang, B. Z. Chem. Phys. Lett., submitted for publication.
31. Tang, B. Z.; Masuda, T.; Higashimura, T.; Yamaoka, H. J. Polym. Sci., Polym. Phys. Ed. 1990, 28, 281.
32. (b) Tang, B. Z.; Masuda, T.; Higashimura, T.; Yamaoka, H. J. Polym. Sci., Polym. Chem. Ed. 1989, 27, 1197.
33. (c) Higashimura, T.; Tang, B. Z.; Masuda, T.; Yamaoka, H.; Matsuyama, T. Polym. J. 1985, 17, 393.
34. Tang, B. Z.; Masuda, T.; Higashimura, T. J. Polym. Sci., Part B: Polym. Phys. 1989, 27, 1261.
35. (b) Masuda, T.; Tang, B. Z.; Higashimura, T. Polym. J. 1986, 18, 565.
36. (c) Masuda, T.; Iguchi, Y.; Tang, B. Z.; Higashimura, T. Polymer 1988, 29, 2041.
37. (d) Masuda, T.; Takatsuka, M.; Tang, B. Z.; Higashimura, T. J. Membr. Sci. 1990, 49, 69.
38. Yashima, E.; Maeda, Y.; Okamoto, Y. J. Am. Chem. Soc. 1998, 120, 8895.
39. (b) Yashima, E.; Matsushima, T.; Okamoto, Y. J. Am. Chem. Soc. 1997, 119, 6345.
40. (c) Kishimoto, Y.; Itou, M.; Miyatake, T.; Ikariya, T.; Noyori, H. Macromolecules 1995, 28, 6662.
41. (d) Yashima, E.; Huang, S.; Okamoto, Y. Chem. Commun. 1994, 1811.
42. (e) Aoki, T.; Kokai, M.; Shinohara, K.; Oikawa, E. Chem. Lett. 1993, 2009.
43. (f) Yamaguchi, M.; Omata, K.; Hirama, M. Chem. Lett. 1992, 2261.
44. (g) Tang, B. Z.; Kotera, N. Japanese Patent H2-258807, 1990.
45. (h) Tang, B. Z. Adv. Mater. 1990, 2, 107.
46. (i) Tang, B. Z.; Kotera, N. Macromolecules 1989, 22, 4388.
47. Stevens, M. P. Polymer Chemistry: an Introduction, 3rd ed.; Oxford University Press: Oxford, 1999.
48. (b) Carraher, C. E., Jr. Polymer Chemistry, 4th ed.; Marcel Dekker; New York, 1996.
49. Goosey, M. In Specialty Polymers; Dyson, R. W., Ed.; Blackie: London, 1987; Chapter 5.
50. (b) Cowie, J. M. G. Polymers: Chemistry & Physics of Modern Materials, 2nd ed.; Blakie: London, 1991.
51. (c) Allenmark, S. Chromatographic Enantioseparation: Methods and Applications, 2nd ed.; Horwood: New York, 1991.
52. (d) Tang, B. Z.; Wan, X.; Kwok, H. S. Eur. Polym. J. 1998, 34, 341.
53. Kishimoto, Y.; Eckerle, P.; Miyatake, T.; Noyori, R. Macromolecules 1996, 29, 5054.
54. (b) Kishimoto, Y.; Eckerle, P.; Miyatake, T.; Ikariya, T.; Noyori, R. J. Am. Chem. Soc. 1994, 116, 12131.
55. Hirao, K.; Ishii, Y.; Terao, T.; Kishimoto, Y.; Miyatake, T.; Ikariya, T.; Noyori, R. Macromolecules 1998, 31, 3405.
56. Iino, K.; Goto, H.; Akagi, K.; Shirakawa, H.; Kawaguchi, A. Synth. Met. 1997, 84, 967.
57. Tonelli, A. E. NMR Spectroscopy and Polymer Microstructure; VCH: New York, 1989.
58. (b) High-Resolution NMR Spectroscopy of Synthetic Polymers in Bulk; Komoroski, R. A., Ed.; VCH: Deerfield Beach, FL, 1986.
59. (c) Katz, T. J.; Hacker, S. M.; Kendrick, R. D.; Yannoni, C. S. J. Am. Chem. Soc. 1985, 107, 2182.
60. (d) Clarke, T. C.; Yannoni, C. S.; Katz, T. J. J. Am. Chem. Soc. 1983, 105, 7787.
61. Silverstein, R. M.; Bassler, G. C.; Morrill, T. C. Spectrometric Identification of Orgainc Compounds, 5th ed.; Wiley: New York, 1991.
62. (b) Williams, D. H.; Fleming, I. Spectroscopic Methods in Organic Chemistry, 4th ed.; McGraw-Hill Book: London, 1989.
63. Simionescu, C. I.; Percec, V.; Dumitrescu, S. J. Polym. Sci., Polym. Chem. Ed. 1977, 15, 2497.
64. (b) Simionescu, C. I.; Percec, V. J. Polym. Sci., Polym. Symp. 1980, 67, 43.
65. The activation energy for the disrotatory ring closure is as low as <30 kcal/mol (data taken from ref 19).
66. Houk, K. N.; Li, Y.; Evanseck, J. D. Angew. Chem., Int. Ed. Engl. 1992, 31, 682.
67. (b) Desimoni, G.; Tacconi, G.; Barco, A.; Pollini, G. P. Natural Products Synthesis through Pericyclic Reactions; American Chemical Society: Washington, DC, 1983.
68. GPC analysis shows that the molecular weight of the polymer decreases; that is, the polymer chain must have been cleaved. We have considered different kinds of chain scission modes, but the one proposed in Scheme 1 seems most likely to occur due to the steric and electronic effects: (i) the chain scission can relieve the steric crowdedness of 7, and (ii) the radicals thus generated can be stabilized by the aromatic ring (R) in 8 and by the phenyl and vinyl groups in 9.
69. Walling, C. Fifty Years of Free Radicals; American Chemical Society: Washington, DC, 1995.
70. (b) Substituent Effects in Radical Chemistry; Viehe, H. G., Janousek, Z., Mereny, R., Eds.; D. Reidel: Dordrecht, Holland, 1986.
71. (c) Thermochemistry and Its Applications to Chemical and Biochemical Systems: the Thermochemistry of Molecules, Ionic Species, and Free Radicals in Relation to the Understanding of Chemical and Biochemical Systems; Riberio da Silva, M. A. V, Ed.; D. Reidel: Dordrecht, Holland, 1984.
72. Tang, B. Z.; Kong, X.; Wan, X.; Peng, H.; Lam, W. Y.; Feng, X.-D.; Kwok, H. S. Macromolecules 1998, 31, 2419.
73. Kong, X.; Tang, B. Z. Chem. Mater. 1998, 10, 3352.
74. (b) Tang, B. Z.; Lam, J. W. Y.; Kong, X.; Kwok, H. S. U.S. Patent pending.
75. (c) Kong, X.; Wan, X.; Feng, X.-D.; Tang, B. Z. Polym. Prepr. 1998, 39 (1), 369.
76. (d) Kong, X.; Wan, X.; Kwok, H. S.; Feng, X.-D.; Tang, B. Z. Chin. J. Polym. Sci. 1998, 16, 185.
77. (e) Tang, B. Z. Prepr. IUPAC World Polym. Congr. 1998, 772.
78. (f) Tang, B. Z. Proc. Int. Symp. Appl. Chem. 1998, 32.
79. (g) Lam, J. W. Y. MPhil Thesis, Hong Kong University of Science & Technology, Aug 1998.
80. (h) Lam, J. W. Y.; Lee, P. S.; Tang, B. Z. Symp. Front. Chem. 1997, 465.
81. (i) Kong, X.; Wan, X. Feng, X.-D.; Tang, B. Z. Symp. Front. Chem. 1997, 463.
82. (j) Kong, X.; Wan, X. Feng, X.-D.; Tang, B. Z. Symp. Front. Chem. 1997, 461.
83. 3, 1.45 (data taken from ref 25).
84. Carey, F. A.; Sundberg, R. J. Advanced Organic Chemistry, 3rd ed.; Plenum: New York, 1990.
85. (b) CRC Handbook of Chemistry and Physics, 75th ed.; Lide, D. R., Ed.; CRC Press: Boca Raton, FL, 1994.
86. Zassinovich, G.; Mestroni, G.; Camus, A. J. Organomet. Chem. 1975, 91, 379.
87. (b) Kolle, U.; Gorissen, R.; Wagner, T. Chem. Ber. 1995, 128, 911.
88. (c) Dictionary of Organometallic Compounds, 2nd ed.; Chapman & Hall: London, 1995.
89. Hesse, M.; Meizer, H.; Zeeh, B. Spectroscopic Method in Organic Chemistry; Thieme: New York. 1997.
90. Percec, V.; Rinalki, P. L. Polym. Bull. 1983, 9, 548.
91. Furlani, A.; Napoletano, C.; Russo, M. V.; Feast, W. J. Polym. Bull. 1986, 16, 311.
92. Abe, Y.; Masuda, T.; Higashimura, T. J. Polym. Sci., Part A: Polym. Chem. 1989, 27, 4267.
93. (b) Masuda, T.; Hamano, T.; Tsuchida, K.; Higashimura, T. Macromolecules 1990, 23, 1374.
94. Yashima, E.; Huang, S.; Matsushima, T.; Okamoto, Y. Macromolecules 1995, 28, 4184.
95. Matsunami, S.; Kakuchi, T.; Ishii, F. Macromolecules 1997, 30, 1074.
96. Cianciusi, A. M.; Furlani, A.; La Ginestra, A.; Russo, M. V.; Palyi, G.; Vizi-Orosz, A. Polymer 1990, 31, 1568.