Construction of hyperbranched poly(alkenephenylene)s by diyne polycyclotrimerization: Single-component catalyst, glycogen-like macromolecular structure, facile thermal curing, and strong thermolysis resistance

Macromolecules

Volumn 37, Issue 14, 2004, Pages 5196-5210

  Zheng, Ronghua ^a   Dong, Hongchen ^a   Peng, Han ^a   Lam, Jacky W Y ^a   Tang, Ben Zhong ^a,b  

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

^b PEKING UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

CARBOHYDRATES; CATALYSTS; CHEMICAL REACTIONS; GLUCOSE; MOLECULAR WEIGHT; MONOMERS; OLEFINS; POLYMERS; STRUCTURAL ANALYSIS; TANTALUM COMPOUNDS; THERMAL EFFECTS; TOLUENE;

ALKENEPHENYLENES; BIPOLYMERS; GLYCOGENS; POLYCYCLOTRIMERIZATIONS;

MACROMOLECULES;

EID: 3242802928     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma049871+     Document Type: Article

References (115)

1. Biopolymers from Polysaccharides and Agroproteins; Gross, R. A., Scholz, C., Eds.; American Chemical Society: Washington, DC, 2001.
2. Small saccharides other than glucose can also form hyperbranched biopolymers. Galactose, for example, can be polymerized into galactogen, a polysaccharide with a branched molecular structure similar to that of glycogen.
3. Teusink, B.; Passarge, J.; Reijenga, C. A.; Esgalhado, E.; van der Weijden, C. C.; Schepper, M.; Walsh, M. C.; Bakker, B. M.; van Dam, K.; Westerhoff, H. V.; Snoep, J. L. Eur. J. Biochem. 2000, 267, 5313-5329.
4. (a) Saier, M. H. Mechanisms and Regulation of Carbohydrate Transport in Bacteria; Academic Press: Orlando, FL, 1985.
5. (b) Shimeno, S. Studies on Carbohydrate Metabolism in Fish; A.A. Balkema: Rotterdam, 1982.
6. Carbohydrate Reserves in Plants: Synthesis and Regulation; Gupta, A. K., Kaur, N., Eds.; Elsevier: New York, 2000.
7. 1,4
8. (a) Dendrimers V: Functional and Hyperbranched Building Blocks, Photophysical Properties, Applications in Materials and Life Sciences; Schalley, C. A., Vogtle, F., Eds.; Springer-Verlag: Berlin, 2003.
9. (b) Dendrimers and Other Dendritic Polymers; Frechet, J. M. J., Tomalia, D. A., Eds.; Wiley: New York, 2002.
10. (a) Zhao, D. H.; Moore, J. S. Chem. Commun. 2003, 807-818,
11. (b) Tomalia, D. A.; Frechet, J. M. J. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 2719-2728.
12. (c) Crooks, R. M. Chem. Phys. Chem. 2001, 2, 644-654.
13. (d) Watson, M. D.; Fechtenkotter, A.; Mullen, K. Chem. Rev. 2001, 101, 1267-1300.
14. (e) Jikei, M.; Kakimoto, M. Prog. Polym. Sci. 2001, 26, 1233-1285.
15. (f) Voit, B. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 2505-2525.
16. (g) Frey, H.; Schlenk, C. Top. Curr. Chem. 2000, 210, 69-129.
17. (h) Siemsen, P.; Livingston, R. C.; Diederich, F. Angew. Chem., Int. Ed. 2000, 39, 2633-2657.
18. (i) Bunz, U. H. F. Chem. Rev. 2000, 100, 1605-1644.
19. (j) Hult, A.; Johansson, M.; Malmstrom, E. Adv. Polym. Sci. 1999, 143, 1-34.
20. (k) Scherf, U. Top. Curr. Chem. 1999, 201, 163-222.
21. (l) Hawker, C. J. Curr. Opin. Colloid Interface Sci. 1999, 4, 117-121.
22. (m) Newkome, G. R.; He, E. F.; Moorefield, C. N. Chem. Rev. 1999, 99, 1689-1746.
23. (n) Bosman, A. W.; Janssen, H. M.; Meijer, E. W. Chem. Rev. 1999, 99, 1655-1688.
24. (o) Kim, Y. H. J. Polym. Sci., Part A: Polym. Chem. 1998, 38, 1685-1698.
25. (a) Miller, T. M.; Neenan, T. X.; Zayas, R.; Bair, H. E. J. Am. Chem. Soc. 1992, 114, 1018-1025.
26. (b) Tour, J. M. Adv. Mater. 1994, 6, 190-198.
27. (c) Johnen, N. A.; Kim, H. K.; Ober, C. K. ACS Symp. Ser. 1994, 579, 298-315.
28. (d) Hecht, S.; Frechet, J. M. J. J. Am. Chem. Soc. 1999, 121, 4084-4085.
29. (e) Mitsutoshi, J.; Ken, F.; Yang, G.; Kakimoto, M. Macromolecules 2000, 33, 6228-6234.
30. (f) Cameron, C.; Fawcett, A. H.; Hetherington, C. R.; Mee, R. A. W.; McBride, F. V. Macromolecules 2000, 33, 6551-6568.
31. (g) Weil, T.; Wiesler, U.-M.; Herrmann, A.; Bauer, R.; Hofkens, J.; De Schryver, F. C.; Mullen, K. J. Am. Chem. Soc. 2001, 123, 8101-8108.
32. (h) Komber, H.; Ziemer, A.; Voit, B. Macromolecules 2002, 35, 3514-3519.
33. (i) Markoski, L. J.; Thompson, J. L.; Moore, J. S. Macromolecules 2002, 35, 1599-1603.
34. (a) Zheng, R.; Lam, J. W. Y.; Peng, H.; Häussler, M.; Tang, B. Z. Polym. Mater. Sci. Eng. 2003, 89, 442-443.
35. (b) Zheng, R.; Lam, J. W. Y.; Peng, H.; Häussler, M.; Law, C. C. W.; Tang, B. Z. Polym. Prepr. 2003, 44 (2), 770-771.
36. (a) Chen, J.; Peng, H.; Law, C. C. W.; Dong, Y.; Lam, J. W. Y.; Williams, I. D.; Tang, B. Z. Macromolecules 2003, 36, 4319-4327.
37. (b) Xu, K.; Peng, H.; Sun, Q.; Dong, Y.; Salhi, F.; Luo, J.; Chen, J.; Huang, Y.; Zhang, D.; Xu, Z.; Tang, B. Z. Macromolecules 2002, 35, 5821-5834.
38. (c) Peng, H.; Cheng, L.; Luo, J.; Xu, K.; Sun, Q.; Dong, Y.; Salhi, F.; Lee, P. P. S.; Chen, J.; Tang, B. Z. Macromolecules 2002, 35, 5349-5351.
39. (d) Peng, H.; Luo, J.; Cheng, L.; Lam, J. W. Y.; Xu, K.; Dong, Y.; Zhang, D.; Huang, Y.; Xu, Z.; Tang, B. Z. Opt. Mater. 2002, 21, 315-320.
40. (e) Xu, K.; Tang, B. Z. Chin. J. Polym. Sci. 1999, 17, 397-402.
41. (a) Mi, Y.; Tang, B. Z. Polym. News 2001, 26, 170-176.
42. (b) Lam, J. W. Y.; Luo, J.; Peng, H.; Xie, Z.; Xu, K.; Dong, Y.; Cheng, L.; Qiu, C.; Kwok, H. S.; Tang, B. Z. Chin. J. Polym. Sci. 2001, 19, 585-590.
43. (c) Lam, J. W. Y.; Chen, J.; Law, C. C. W.; Peng, H.; Xie, Z.; Cheuk, K. K. L.; Kwok, H. S.; Tang, B. Z. Macromol. Symp. 2003, 196, 289-300.
44. (d) Xie, Z.; Peng, H.; Lam, J. W. Y.; Chen, J.; Zheng, Y.; Qiu, C.; Kwok, H. S.; Tang, B. Z. Macromol. Symp. 2003, 195, 179-184.
45. (e) Häussler, M.; Lam, J. W. Y.; Zheng, R.; Peng, H.; Luo, J.; Chen, J.; Law, C. C. W.; Tang, B. Z. C. R. Chim. 2003, 6, 833-842.
46. Xu, K. Ph.D. Dissertation, Hong Kong University of Science &Technology, Dec 2000.
47. (a) Muchtar, Z.; Schappacher, M.; Deffieux, A. Macromolecules 2001, 34, 7595.
48. (b) Grayson, S. M.; Frechet, J. M. J. Macromolecules 2001, 34, 6542.
49. (c) Uhrich, K. E.; Hawker, C. J.; Frechet, J. M. J.; Turner, S. R. Macromolecules 1992, 25, 4583.
50. Zheng, R.; Peng, H.; Lam, J. W. Y.; Chen, J.; Häussler, M.; Tang, B. Z. Polym. Prepr. 2003, 44 (1), 956-957.
51. (a) Xu, K.; Peng, H.; Lam, J. W. Y.; Poon, 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.
52. (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.
53. (c) Tang, B. Z.; Poon, W. H.; Leung, S. M.; Leung, W. H.; Peng, H. Macromolecules 1997, 30, 2209-2212.
54. (d) Tang, B. Z.; Kotera, N. Macromolecules 1989, 22, 4388-4390.
55. Lam, J. W. Y.; Tang, B. Z. J. Polym. Sci., Part A: Polym. Chem. 2003, 41, 2607-2629.
56. (a) Preliminary results have been reported in ref 9b.
57. (b) Zheng, R.; Dong, H.; Lam, J. W. Y.; Tang, B. Z. Manuscript in preparation.
58. (a) Handbook of Metathesis; Grubbs, R. H., Ed.; Wiley-VCH: Weinheim, 2003.
59. (b) Choi, S. K.; Gal, Y. S.; Jin, S. H.; Kim, H. K. Chem. Rev. 2000, 100, 1645-1681.
60. (c) Metathesis Polymerization of Olefins and Polymerization of Alkynes; Imamoglu, Y., Ed.; Kluwer: Boston, 1998.
61. (d) Ivin, K. J.; Mol, J. C. Olefin Metathesis and Metathesis Polymerization; Academic Press: San Diego, 1997.
62. (e) Ginsburg, E. J.; Gorman, C. B.; Grubbs, R. H. In Modern Acetylene Chemistry; Stang, P. J., Diederich, F., Eds.; VCH: Weinheim, 1995; Chapter 10.
63. (f) 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.
64. (a) Lam, J. W. Y.; Dong, Y.; Cheuk, K. K. L.; Luo, J.; Xie, Z.; Kwok, H. S.; Mo, Z.; Tang, B. Z. Macromolecules 2002, 35, 1229-1240.
65. (b) Tang, B. Z.; Xu, H.; Lam, J. W. Y.; Lee, P. P. S.; Xu, K.; Sun, Q.; Cheuk, K. K. L. Chem. Mater. 2000, 12, 1446-1455.
66. (c) Huang, Y. M.; Lam, J. W. Y.; Cheuk, K. K. L.; Ge, W.; Tang, B. Z. Macromolecules 1999, 32, 5976-5978.
67. (d) Tang, B. Z.; Kong, X.; Wan, X.; Peng, H.; Lam, W. Y.; Feng, X.; Kwok, H. S. Macromolecules 1998, 31, 2419-2432.
68. (a) Silverstein, R. M.; Webster, F. X. Spectrometric Identification of Organic Compounds, 6th ed.; Wiley: New York, 1998.
69. (b) Pretsch, E.; Buhlmann, P.; Affolter, C. Structure Determination of Organic Compounds: Tables of Spectral Data, 3rd ed.; Springer: Berlin, 2000.
70. (c) Field, L. D.; Sternhell, S.; Kalman, J. R. Organic Structures from Spectra, 3rd ed.; Wiley: New York, 2002.
71. Masuda, T.; Tang, B. Z.; Higashimura, T.; Yamaoka, H. Macromolecules 1985, 18, 2369-2373.
72. Goosy, M. In Specialty Polymers; Dyson, R. W., Ed.; Blackie: London, 1987; Chapter 5, pp 83-109.
73. (a) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901-2915.
74. (b) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49-92.
75. (c) Schore, N. E. Chem. Rev. 1988, 88, 1081-1119.
76. (d) Vollhardt, K. P. C. Angew. Chem., Int. Ed. Engl. 1984, 23, 539-644.
77. (e) Maitlis, P. M. Acc. Chem. Res. 1976, 9, 93-99.
78. (a) Cotton, F. A.; Hall, W. T. J. Am. Chem. Soc. 1979, 101, 5094-5095.
79. (b) Bruck, M. A.; Copenhaver, A. S.; Wigley, D. E. J. Am. Chem. Soc. 1987, 109, 6525-6527.
80. (c) Strickler, J. R.; Wexler, P. A.; Wigley, D. E. Organometallics 1988, 7, 2067-2069.
81. (d) Bianchini, C.; Caulton, K. G.; Chardon, C.; Eisenstein, O.; Folting, K.; Johnson, T. J.; Meli, A.; Peruzzini, M.; Rauscher, D. J.; Streib, W. E.; Vizza, F. J. Am. Chem. Soc. 1991, 113, 5127-5129.
82. (e) Strickler, J. R.; Wexler, P. A.; Wigley, D. E. Organometallics 1991, 10, 118-127.
83. (f) Kwon, D.; Real, J.; Curtis, M. D.; Rheingold, A.; Haggerty, B. S. Organometallics 1991, 10, 143-148.
84. (g) Pope, R. M.; Vanorden, S. L.; Cooper, B. T.; Buckner, S. W. Organometallics 1992, 11, 2001-2003.
85. (h) Pelissier, H.; Rodriguez, J.; Vollhardt, K. P. C. Chem.-Eur. J. 1999, 5, 3549-3561.
86. 1H FT NMR Spectra; Aldrich Chemical Co., Ltd.: Milwaukee, WI, 1993.
87. (b) Feinstein, K. Guide to Spectroscopic Identification of Organic Compounds; CRC Press: Boca Raton, FL, 1995.
88. (a) Matsuzaki, K.; Uryu, T.; Asakura, T. NMR Spectroscopy and Stereoregularity of Polymers; Japan Scientific Societies Press: Tokyo, 1996.
89. (b) Bovey, F. A.; Mirau, P. A. NMR of Polymers; Academic Press: San Diego, CA, 1996.
90. (c) NMR Spectroscopy of Polymers in Solution and in the Solid State; Cheng, H. N., English, A. D., Eds.; American Chemical Society: Washington, DC, 2003.
91. (a) Carraher, C. E., Jr. Seymour/Carraher's Polymer Chemistry, 6th ed.; M. Dekker: New York, 2003.
92. (b) Stevens, M. P. Polymer Chemistry: an Introduction, 3rd ed.; Oxford University Press: New York, 1999.
93. (a) Markoski, L. J.; Thompson, J. L.; Moore, J. S. Macromolecules 2002, 35, 1599-1603.
94. (b) Hölter, D.; Burgath, A.; Frey, H. Acta Polym. 1997, 48, 30-35.
95. 10,12,20,25 (indeed, if L exhibited resonance peaks different from those of D, that would be very helpful because it would make the estimation of the LID molar ratio a straightforward, easy job.)
96. (a) Hawker, C. J.; Lee, R.; Fréchet, J. M. J. J. Am. Chem. Soc. 1991, 113, 4583-4588.
97. (b) Frey, H.; Hölter, D. Acta Polym. 1999, 50, 67-76.
98. (a) Wang, M.; Gan, D.; Wooley, K. L. Macromolecules 2001, 34, 3215-3223.
99. (b) Parker, D.; Feast, W. J. Macromolecules 2001, 34, 2048-2059.
100. (c) Thompson, D. S.; Markoski, L. J.; Moore, J. S.; Sendijarevic, I.; Lee, A.; McHugh, A. J. Macromolecules 2000, 33, 6412-6415.
101. (d) Radke, W.; Litvinenko, G.; Muller, A. H. E. Macromolecules 1998, 31, 239-248.
102. (e) Yan, D. Y.; Muller, A. H. E.; Matyjaszewski, K. Macromolecules 1997, 30, 7024-7033.
103. (f) Kim, Y. H.; Webster, O. W. Macromolecules 1992, 25, 5561-5572.
104. (a) Gherghel, L.; Kubel, C.; Lieser, G.; Rader, H. J.; Mullen, K. J. Am. Chem. Soc. 2002, 124, 13130-13138.
105. (b) Dai, L. M.; Patil, A.; Gong, X. Y.; Guo, Z. X.; Liu, L. Q.; Liu, Y.; Zhu, D. B. Chem. Phys. Chem. 2003, 4, 1150-1169.
106. (c) Park, C.; Yoon, J.; Thomas, E. L. Polymer 2003, 44, 6725-6760.
107. Tang, B. Z.; Xu, H. Macromolecules 1999, 32, 2569-2576.
108. (a) Simon, P. F. W.; Ulrich, R.; Spiess, H. W.; Wiesner, U. Chem. Mater. 2001, 13, 3464-3486.
109. (b) Corriu, R. J. P. Angew. Chem., Int. Ed. 2000, 39, 1376-1398.
110. (c) Interrante, L. V.; Liu, Q.; Rushkin, I.; Shen, Q. Appl. Organomet. Chem. 1996, 10, 1-10.
111. (d) Birot, M.; Pillot, J. P.; Dunogues, J. Chem. Rev. 1995, 95, 1443-1477.
112. (e) Seyferth, D. Adv. Chem. Ser. 1995, 245, 131-160.
113. (a) Sun, Q. H.; Xu, K. T.; Peng, H.; Zheng, R. H.; Haussler, M.; Tang, B. Z. Macromolecules 2003, 36, 2309-2320.
114. (b) Sun, Q.; Xu, K.; Lam, J. W. Y.; Cha, J. A. P.; Zhang, X.; Tang, B. Z. Mater. Sci. Eng., C 2001, 16, 107-112.
115. (c) Sun, Q.; Lam, J. W. Y.; Xu, K.; Xu, H.; Cha, J. A. P.; Wong, P. C. L.; Wen, G.; Zhang, X.; Jing, X.; Wang, F.; Tang, B. Z. Chem. Mater. 2000, 12, 2617-2624.