Exploration of effective catalysts for diyne polycyclotrimerization, synthesis of an ester-functionalized hyperbranched polyphenylene, and demonstration of its utility as a molecular container with implication for controlled drug delivery

Macromolecules

Volumn 42, Issue 19, 2009, Pages 7367-7378

  Liu, Jianzhao ^a   Zhang, Li ^a   Lam, Jacky W Y ^a   Jim, Cathy K W ^a   Yue, Yanan ^b   Deng, Rui ^b   Hong, Yuning ^a   Qin, Anjun ^a,c   Sung, Herman H Y ^a   Williams, Ian D ^a   Jia, Guochen ^a   Tang, Ben Zhong ^a,c  

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

^b CHINESE UNIVERSITY OF HONG KONG   (Hong Kong)

^c ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ARYLENE; CYCLOPENTADIENYLS; DEGREE OF BRANCHING; DRUG CARRIER; FUNCTIONALIZED; GOOD YIELD; HIGH MOLECULAR WEIGHT; HIGH TRANSPARENCY; HYDROGEN-BOND INTERACTIONS; HYDROLYSIS REACTION; HYPERBRANCHED; HYPERBRANCHED POLYMERS; MOLECULAR CONTAINERS; POLYCYCLOTRIMERIZATION; POLYMERIZATION REACTION; POLYPHENYLENES; RUTHENIUM CATALYSTS; SMALL MOLECULES; TOPOLOGICAL STRUCTURE; VISIBLE SPECTRAL REGIONS;

CATALYSIS; CATALYSTS; DENDRIMERS; DRUG THERAPY; ESTERIFICATION; ESTERS; HYDROGEN; OLEFINS; POLYMERS; RUTHENIUM; RUTHENIUM COMPOUNDS; STRUCTURAL OPTIMIZATION;

CONTROLLED DRUG DELIVERY;

EID: 70350006776     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma901247q     Document Type: Article

References (73)

1. For examples of general reviews on hyperbranched polymers, see.
2. (a) Gao, C.; Yan, D. Prog. Polym. Sci. 2004, 29, 183.
3. (b) Tomalia, D. A.; Frechet, J. M. J. Polym. Sci., Part A: Polym. Chem. 2002, 40, 2719.
4. (c) Jikei, M.; Kakimoto, M. Prog. Polym. Sci. 2001, 26, 1233.
5. (d) Voit, B. J. Polym. Sci., Part A: Polym. Chem. 2000, 38, 2505.
6. (e) Pattern, T. E.; Matyjaszewski, K. Adv. Mater. 1998,10, 901.
7. For examples of reviews about our research program on hyperbranched polymers, see: (a) Liu, J.; Lam, J. W. Y.; Tang, B. Z. Chem. Rev. 2009, 109, 10.1021/cr900149d.
8. (b) Haussler, M.; Tang, B. Z. Adv. Polym. Sci. 2007, 209, 1.
9. (c) Haussler, M.; Lam, J. W. Y.; Zheng, Y.; Peng, H.; Luo, J.; Chen, J.; Law, C. C. W.; Tang, B. Z. C. R. Chim. 2003,196, 289.
10. Liu, J.; Zheng, R.; Tang, Y.; Haussler, M.; Lam, J. W. Y.; Qin, A.; Ye, M.; Hong, Y.; Gao, P.; Tang, B. Z. Macromolecules 2007, 40, 7473.
11. (a) Irzhak, T. F.; Irzhak, V. I.; Malkov, G. V.; Estrin, Ya. I.; Badamshina, E. R. J. Polym. Sci., Ser. A 2008,50, 74.
12. (b) Irzhak, T. F.; Irzhak, V. I.; Malkov, G. V.; Estrin, Ya. I.; Badamshina, E. R. J. Polym. Sci., Ser. B 2009, 51, 183.
13. Zheng, R.; Haussler, M.; Dong, H.; Lam, J. W. Y.; Tang, B. Z. Macromolecules 2006, 39, 7973.
14. (a) Haussler, M.; Qin, A.; Tang, B. Z. Polymer 2007, 48, 6181.
15. (b) Zheng, R.; Dong, H. C.; Tang, B. Z. In Macromolecules Containing Metal- and Metal-like Elements; Abd-El-Aziz, A., Carraher, C., Pittman, C., Sheats, J., Zeldin, M., Eds.; Wiley: New York, 2005; Vol.4, Chapter 2, pp 7-36.
16. Haussler, M.; Liu, J. Z.; Zheng, R.; Tang, B. Z. Macromolecules 2007, 40, 1914.
17. (a) Saito, S.; Yamamoto, Y. Chem. Rev. 2000, 100, 2901.
18. (b) Yamamoto, Y. CuurrOjrgOhem. 2005, 9, 503.
19. (a) Kirchner, K.; Calhorda, M. J.; Schmid, R.; Veiros, L. F. J. Am. Chem. Soc. 2003,125, 11721.
20. (b) Cadierno, V.; Garcia-Garrido, S. E.; Gimeno, J. J. Am. Chem. Soc. 2006, 128, 15094.
21. Lindner, E.; Haustein, M.; Mayer, H. A.; Gierling, K.; Fawzi, R.; Steimann, M. Organometallics 1995, 14, 2246.
22. Bruce, M. I.; Hameister, C.; Swincer, A. G.; Wallis, R. C. Inorg. Synth. 1990, 28, 270.
23. Oshima, N.; Suzuki, H.; Moro-oka, Y. Chem. Lett. 1984, 1161.
24. Cox, D. N.; Roulet, R. Inorg. Chem. 1990, 29, 1360.
25. (a) Gemel, C.; LaPensee, A.; Mauthner, K.; Mereiter, K.; Schmid, R.; Kirchner, K. Monatsh. Chem. 1997,128, 1189-1199.
26. (b) Ernst, C.; Walter, O.; Dinjus, E. J. Prakt. Chem. 1999, 341, 801.
27. Albers, M. O.; de Waal, D. J. A.; Liles, D. C.; Robinson, D. J.; Singleton, E.; Wiege, M. B. J. Chem. Soc., Chem. Commun. 1986, 1680.
28. (a) Otsuka, E.; Kurumada, K.; Suzuki, A.; Matsuzawa, S.; Takeu- chi, K. J. Sol-Gel Sci. Technol. 2008,46,71.
29. (b) Chu, J. B.; Huang, S. M.; Zhu, H. B.; Xu, X. B.; Sun, Z.; Chen, Y. W.; Huang, F. Q. J. Non- Cryst. Solids 2008, 354, 5480.
30. Funke, W.; Okay, O.; Joos-Muller, B. Adv. Polym. Sci. 1998,136, 139.
31. (a) Hawker, C. J.; Malmstrom, E. E.; Curtis, W. F.; Kampf, J. P. J Am. Chem. Soc. 1997, 119, 9903.
32. (b) Harth, E. M.; Hecht, S.; Helms, B.; Malmstrom, E. E.; Frechet, J. M. J.; Hawker, C. J. J. Am. Chem. Soc. 2002, 124, 3926.
33. (a) Jansen, J.; de Brabander-van den Berg, E. M.; Meijer, E. W. Science 1994, 266, 1226.
34. (b) Gorman, C. B.; Smith, J. C. Acc. Chem. Res. 2001, 34, 60.
35. (c) Crooks, R. M.; Zhao, M.; Sun, L.; Chechik, V.; Yeung, L. K. Acc. Chem. Res. 2001, 34, 181.
36. (d) Vogtle, F.; Gester- mann, S.; Hesse, R.; Schwierz, H.; Windisch, B. Prog. Polym. Sci. 2000, 25, 987.
37. (e) Aulenta, F.; Hayes, W.; Rannard, S. Eur. Polym. J. 2003, 39, 1741.
38. (f) Stiriba, S.; Frey, H.; Haag, R. Angew. Chem.. Int. Ed. 2002, 41, 1329.
39. (a) Fu, Y.; VanOosterwijck, C.; Vandendriessche, A.; Kowalczuk- Bleja, A.; Zhang, X.; Dworak, A.; Dehaen, W.; Smet, M. Macromolecules 2008, 41, 2388.
40. (b) Shu, C. F.; Leu, C. M. Macromolecules 1999,32,100.
41. (c) Sunder, A.; Kramer, M.; Hanselmann, R.; Miilhaupt, R.; Frey, H. Angew. Chem., Int. Ed. 1999, 38, 3552.
42. For examples of recent reviews, see: (a) Hong, Y. N.; Lam, J. W. Y.; Tang, B. Z. Chem. Commun. 2009,4332.
43. (b) Liu, J.; J. W., Y.; Tang, B. Z. J. Inorg. Organomet. Polym. Mater. 2009,19,249.
44. (c) Qian, L.; Zhi, J.; Tong, B.; Yang, F.; Zhao, W.; Dong, Y. Prog. Chem. 2008, 20,673.
45. (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.
46. (b) Chen, J.; Law, C. W.; Lam, J. W. Y.; Dong, Y.; Lo, S. M. F.; Williams, I. D.; Zhu, D.; Tang, B. Z. Chem. Mater. 2003,15,1535.
47. (c) Hong, Y. N.; Haussler, M.; Lam, J. W. Y.; Li, Z.; Sin, K. K.; Dong, Y. Q.; Tong, H.; Liu, J. Z.; Qin, A. J.; Renneberg, R.; Tang, B. Z. Chem.-Eur. J. 2008,14,6428.
48. (d) Li, Z.; Dong, Y. Q.; Lam, J. W. Y.; Sun, J. X.; Qin, A. J.; Haussler, M.; Dong, Y. P.; Sung, H. H. Y.; Williams, I. D.; Kwok, H. S.; Tang, B. Z. Adv. Funct. Mater. 2009, 19, 905.
49. (e) Zhao, Z.; Wang, Z.; Lu, P.; Chan, C. Y. K.; Liu, D.; Lam, J. W. Y.; Sung, H. H. Y.; Williams, I. D.; Ma, Y.; Tang, B. Z. Angew. Chem., Int. Ed. 2009, 48, 10.1002/anie.200903698.
50. (a) An, B.-K.; Kwon, S.-K.; Jung, S.-D.; Park, S. Y. J. Am. Chem. Soc. 2002, 124, 14410.
51. (b) Yeh, H. C.; Yeh, S. J.; Chen, C. T. Chem. Commun. 2003, 2632.
52. (c) Chen, J.; Xu, B.; Ouyang, X.; Tang, B. Z.; Cao, Y. J. Phys. Chem. A 2004,108,7522.
53. (d) Toal, S. J.; Jones, K. A.; Magde, D.; Trogler, W. C. J. Am. Chem. Soc. 2005, 127, 11661.
54. (e) Wang, Z.; Shao, H.; Ye, J.; Tang, L.; Lu, P. J. Phys. Chem. B 2005, 109,19627.
55. (f) Yu, G.; Yin, S.; Liu, Y. Q.; Chen, J.; Xu, X.; Sun, X.; Ma, D.; Zhan, X.; Peng, Q.; Shuai, Z. G.; Tang, B. Z.; Zhu, D. B.; Fang, W.; Luo, Y. J. Am. Chem. Soc. 2005,127, 6335.
56. (g) Itami, K.; Yoshida, J. Bull. Chem. Soc. Jpn. 2006, 79,811-824.
57. (h) Han, M. R.; Hirayama, Y.; Hara, M. Chem. Mater. 2006,18,2784.
58. (i) Bhongale, C. J.; Hsu, C.- S. Angew. Chem.. Int. Ed. 2006,45, 1404.
59. (j) Kim, S.; Zheng, Q.; He, G. S.; Bharali, D. J.; Pudavar, H. E.; Baev, A.; Prasad, P. N. Adv. Funct. Mater. 2006,16,2317.
60. (k) Peng, Q.; Yi, Y.; Shuai, Z.; Shao, J. J. Chem. Phys. 2007,126, 114302.
61. (l) Li, Y.; Li, F.; Zhang, H.; Xie, Z.; Xie, W.; Xu, H.; Li, B.; Shen, F.; Ye, L.; Hanif, M.; Ma, D.; Ma, Y. Chem. Commun. 2007,231.
62. (m) Liu, Y.; Tao,X.; Wang, F.; Shi, J.; Sun, J.; Yu, W.; Ren, Y.; Zou, D.; Jiang, M. J. Phys. Chem. C 2007, 111, 6544.
63. (n) Qian, Y.; Li, S.; Zhang, G.; Wang, Q.; Wang, S.;Xu, H.; Li, C.; Li, Y.; Yang, G. J. Phys. Chem. B 2007,111, 5861.
64. (o) Li, C.; Liu, X.; Yuan, M.; Li, J.; Guo, Y.; Xu, J.; Zhu, M.; Lv, J.; Liu, H.; Li, Y. Langmuir 2007,23,6754.
65. (p) Shiraishi, K.; Kashiwabara, T.; Sanji, T.; Tanaka, M. New J. Chem. 2009, 33, 1680.
66. (q) Zheng, Y.; Hu, Y. J. Org. Chem. 2009, 74, 5660.
67. (r) Yang, Z.; Chi, Z.; Yu, T.; Zhang, X.; Chen, M.; Xu, B.; Liu, S.;Zhang, Y.; Xu, J. J. Mater. Chem. 2009,19,5541.
68. (s) He, J.; Xu, B.; Chen, F.; Xia, H.; Li, K.; Ye, L.; Tian, W. J. Phys. Chem. C 2009, 113, 9892.
69. (t) Wang, M.; Zhang, D.; Zhang, G.; Zhu, D. Chem. Phys. Lett. 2009,475,1.
70. (u) Iida, A.; Yamaguchi, S. Chem. Commun. 2009, 3002.
71. (v) Shimizu, M.; Takeda, Y.; Higashi, M.; Hiyama, T. Angew. Chem.. Int. Ed. 2009, 48, 3653.
72. Xing, C. M.; Hong, Y. N.; Dong, Y. Q.; Lam, J. W. Y.; Qin, A. J.; Haussler, M.; Tang, B. Z. Polym. Prepr. 2007, 48, 466.
73. Lam, J. W. Y.; Luo, J.; Dong, Y.; Cheuk, K. K. L.; Tang, B. Z. Macromolecules 2002, 35, 8288.