Silole-containing poly(silylenevinylene)s: Synthesis, characterization, aggregation-enhanced emission, and explosive detection

Journal of Polymer Science, Part A: Polymer Chemistry

Volumn 50, Issue 11, 2012, Pages 2265-2274

  Zhao, Zujin ^a   Jiang, Tao ^a,b   Guo, Yanju ^a   Ding, Liyuan ^a   He, Bairong ^a   Chang, Zhengfeng ^a   Lam, Jacky W Y ^b   Liu, Jianzhao ^b   Chan, Carrie Y K ^b   Lu, Ping ^c   Xu, Liwen ^a   Qiu, Huayu ^a   Tang, Ben Zhong ^b  

^a HANGZHOU NORMAL UNIVERSITY   (China)

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

^c Jilin University   (China)

Author keywords

aggregation enhanced emission; explosive detection; fluorescence; heteroatom containing polymers; synthesis

Indexed keywords

AGGREGATE STATE; AQUEOUS MIXTURES; CHEMO-SENSORS; DECOMPOSITION TEMPERATURE; E-CONTENT; EMISSION CHARACTERISTICS; EXPLOSIVE DETECTION; FILM STATE; HETEROATOM-CONTAINING POLYMERS; HIGH MOLECULAR WEIGHT; HIGH YIELD; OPTIMUM CONDITIONS; PICRIC ACID; POLYHYDROSILYLATION; PROCESSABLE; QUENCHING CONSTANT; STEREOREGULARITY; TETRA-HYDROFURAN; THERMALLY STABLE; WEIGHT LOSS;

ACETYLENE; AGGREGATES; BENZENE; EXPLOSIVES DETECTION; FLUORESCENCE; HYDROSILYLATION; RHODIUM; SYNTHESIS (CHEMICAL); THIOPHENE;

POLYMERS;

EID: 84860324045     PISSN: 0887624X     EISSN: 10990518     Source Type: Journal    
DOI: 10.1002/pola.26006     Document Type: Article

References (88)

1. (a), Khabashesku, V. N.,;, Balaji, V.,;, Boganov, S. E.,;, Nefedov, O. M.,;, Michl, J., J. Am. Chem. Soc. 1994, 116, 320-329
2. (b), Tamao, K.,;, Yamaguchi, S.,;, Ito, Y.,;, Matsuzaki, Y.,;, Yamabe, T.,;, Fukushima, M.,; Macromolecules 1995, 28, 8668-8675
3. (c), Tamao, K.,;, Ohno, S.,;, Yamaguchi, S., Chem. Commun. 1996, 1873-1874
4. (d), Yamaguchi, S.,;, Tamao, K., J. Chem. Soc., Dalton Trans. 1998, 3693-3702
5. (e), Chan, L. H.,;, Lee, R. H.,;, Hsieh, C. F.,;, Yeh, H. C.,;, Chen, C. T., J. Am. Soc. Chem. 2002, 124, 6469-6479
6. (f), Chan, L. H.,;, Yeh, H. C.,;, Chen, C. T., Adv. Mater. 2001, 13, 1637-1641
7. (g), Murata, H.,;, Malliaras, G. G.,;, Uchida, M.,;, Shen, Y.,;, Kafafi, Z. H., Chem. Phys. Lett. 2001, 339, 161-166
8. (h), Mäkinen, A. J.,;, Uchida, M.,;, Kafafi, Z. H., J. Appl. Phys. 2004, 95, 2832-2838.
9. (a), Luo, J.,;, Xie, Z.,;, Lam, J. W. Y.,;, Cheng, L.,;, Chen, H.,;, Qiu, C.,;, Kwok, H. S.,;, Zhan, X.,;, Liu, Y.,;, Zhu, D.,;, Tang, B. Z., Chem. Commun. 2001, 1740-1741
10. (b), Hong, Y.,;, Lam, J. W. Y.,;, Tang, B. Z., Chem. Commun. 2009, 4332-4353
11. (c), Liu, J.,;, Lam, J. W. Y.,;, Tang, B. Z., J. Inorg. Organomet. Polym. Mater. 2009, 19, 249-285
12. (d), Hong, Y.,;, Lam, J. W. Y.,;, Tang, B. Z., Chem. Soc. Rev. 2011, 40, 5361-5388
13. (e), Qin, A.,;, Lam, J. W. Y.,;, Tang, B. Z., Prog. Polym. Sci. 2012, 37, 182-209.
14. (a), Li, Z.,;, Dong, Y.,;, Mi, B.,;, Tang, Y.,;, Häussler, M.,;, Tong, H.,;, Dong, Y.,;, Lam, J. W. Y.,;, Ren, Y.,;, Sun, H. H. Y.,;, Wong, K. S.,;, Gao, P.,;, Williams, I. D.,;, Kwok, H. S.,;, Tang, B. Z., J. Phys. Chem. B 2005, 109, 10061-10066
15. (b), Dong, Y.,;, Lam, J. W. Y.,;, Li, Z.,;, Tong, H.,;, Dong, Y.,;, Feng, X. D.,;, Tang, B. Z., J. Inorg. Organomet. Polym. Mater. 2005, 15, 287-291
16. (c), 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, 7608-7611
17. (d), Yu, G.,;, Yin, S.,;, Liu, Y.,;, Chen, J.,;, Xu, X.,;, Sun, X.,;, Ma, D.,;, Zhan, X.,;, Peng, Q.,;, Shuai, Z.,;, Tang, B. Z.,;, Zhu, D.,;, Fang, W.,;, Luo, Y., J. Am. Chem. Soc. 2005, 127, 6335-6346.
18. (a), Tamao, K.,;, Uchida, M.,;, Izumizawa, T.,;, Fukukawa, K.,;, Yamaguchi, S., J. Am. Chem. Soc. 1996, 118, 11974-11975
19. (b), Uchida, M.,;, Izumizawa, T.,;, Nakano, T.,;, Yamaguchi, S.,;, Tamao, K.,;, Furukawa, K., Chem. Mater. 2001, 13, 2680-2683
20. (c), Murata, H.,;, Kafafi, Z. H.,;, Uchida, M., Appl. Phys. Lett. 2002, 80, 189-191
21. (d), Liu, Y.,;, Chen, Z.,;, Chen, J.,;, Wang, F.,;, Cao, Y., Polym. Bull. 2007, 59, 31-44
22. (e), Geramita, K.,;, McBee, J.,;, Shen, Y.,;, Radu, N.,;, Tilley, T. D., Chem. Mater. 2006, 18, 3261-3265
23. (f), Son, H.-J.,;, Han, W.-S.,;, Chun, J.-Y.,;, Lee, C.-J.,;, Han, J.-I.,;, Ko, J.,;, Kang, S. O., Organometallics 2007, 26, 519-526
24. (g), Tang, B. Z.,;, Zhan, X.,;, Yu, G.,;, Lee, P. P. S.,;, Liu, Y.,;, Zhu, D., J. Mater. Chem. 2001, 11, 2974-2978
25. (h), Zhao, Z.,;, Chen, S.,;, Lam, J. W. Y.,;, Jim, C. K. W.,;, Chan, C. Y. K.,;, Wang, Z.,;, Lu, P.,;, Kwok, H. S.,;, Ma, Y.,;, Tang, B. Z., J. Phys. Chem. C 2010, 114, 7963-7972
26. (i), Du, X.,;, Wang, Z. Y., Chem. Commun. 2011, 47, 4276-4278.
27. (a), Mi, B.,;, Dong, Y.,;, Li, Z.,;, Lam, J. W. Y.,;, Häußler, M.,;, Sung, H. H. Y.,;, Kwok, H. S.,;, Dong, Y.,;, Williams, I. D.,;, Liu, Y.,;, Luo, Y.,;, Shuai, Z.,;, Zhu, D.,;, Tang, B. Z., Chem. Commun. 2005, 3583-3585
28. (b), Wang, F.,;, Luo, J.,;, Yang, K.,;, Chen, J.,;, Huang, F.,;, Cao, Y., Macromolecules 2005, 38, 2253-2260
29. (c), Chen, J.,;, Cao, Y., Macromol. Rapid Commun. 2007, 28, 1714-1742
30. (d), Hong, Y.-R.,;, Wong, H.-K.,;, Moh, L. C. H.,;, Tan, H.-S.,;, Chen, Z.-K., Chem. Commun. 2011, 47, 4920-4922
31. (e), Song, J.,;, Du. C.,;, Li, C.,;, Bo, Z., J. Polym. Sci. Part A: Polym. Chem. 2011, 49, 4267-4274.
32. (a), Yu, Y.,;, Feng, C.,;, Hong, Y.,;, Liu, J.,;, Chen, S.,;, Ng, K. M.,;, Luo, K. Q.,;, Tang, B. Z., Adv. Mater. 2011, 23, 3298-3302
33. (b), Yu, Y.,;, Hong, Y.,;, Feng, C.,;, Liu, J.,;, Lam, J. W. Y.,;, Faisal, M.,;, Ng, K. M.,;, Luo, K. Q.,;, Tang, B. Z., Sci. China Ser. B: Chem. 2009, 52, 15-19
34. (c), Faisal, M.,;, Yu, Y.,;, Lam, J. W. Y.,;, Liu, J.,;, Zhang, B.,;, Lu, P.,;, Zhang, X.,;, Tang, B. Z., Adv. Funct. Mater. 2011, 21, 1733-1740.
35. (a), Li, Z.,;, Dong, Y.,;, Lam, J. W. Y.,;, Sun, J.,;, Qin, A.,;, Häußler, M.,;, Dong, Y.,;, Sung, H. H. Y.,;, Williams, I. D.,;, Kwok, H. S.,;, Tang, B. Z., Adv. Funct. Mater. 2009, 19, 905-917
36. (b), Hatano, K.,;, Saeki, H.,;, Yokota, H.,;, Aizawa, H.,;, Koyama, T.,;, Matsuoka, K.,;, Terunuma, D., Tetrahedron Lett. 2009, 50, 5816-5819
37. (c), Toal, S. J.,;, Jones, K. A.,;, Magde, D.,;, Trogler, W. C., J. Am. Chem. Soc. 2005, 127, 11661-11665
38. (d), Dong, Y.,;, Lam, J. W. Y.,;, Qin, A.,;, Li, Z.,;, Liu, J.,;, Sun, J. Z.,;, Dong, Y.,;, Tang, B. Z., Chem. Phys. Lett. 2007, 446, 124-127
39. (e), Wang, M.,;, Zhang, D.,;, Zhang, G.,;, Tang, Y.,;, Wang, S.,;, Zhu, D., Anal. Chem. 2008, 80, 6443-6448
40. (f), Liu, Z.,;, Xue, W.,;, Cai, Z.,;, Zhang, G.,;, Zhang, D., J. Mater. Chem. 2011, 21, 14487-14491
41. (g), Liu, Y.,;, Tang, Y.,;, Barashkov, N. N.,;, Irgibaeva, I. S.,;, Lam, J. W. Y.,;, Hu, R.,;, Birimzhanova, D.,;, Yu, Y.,;, Tang, B. Z., J. Am. Chem. Soc. 2010, 132, 13951-13953
42. (h), Zhao, Z.,;, Liu, J.,;, Lam, J. W. Y.,;, Chan, C. Y. K.,;, Qiu, H.,;, Tang, B. Z., Dyes Pigments 2011, 91, 258-263.
43. (a), Steinfeld, J. I.,;, Wormhoudt, J., Annu. Rev. Phys. Chem. 1998, 49, 203-232
44. (b), Albert, K. J.,;, Lewis, N. S.,;, Schauer, C. L.,;, Sotzing, G. A.,;, Stitzel, S. E.,;, Vaid, T. P.,;, Walt, D. R., Chem. Rev. 2000, 100, 2595-2626
45. (c), Singh, S., J. Hazard. Mater. 2007, 144, 15-28
46. (d), Lee, Y. H.,;, Liu, H.,;, Lee, J. Y.,;, Kim, S. H.,;, Kim, S. K.,;, Sessler, J. L.,;, Kim, Y.,;, Kim, J. S., Chem. Eur. J. 2010, 16, 5895-5901
47. (e), Xu, B.,;, Wu, X.,;, Li, H.,;, Tong, H.,;, Wang, L., Macromolecules 2011, 44, 5089-5092
48. (f), Cavaye, H.,;, Shaw, P. E.,;, Wang, X.,;, Burn, P. L.,;, Lo, S.-C.,;, Meredith, P., Macromolecules 2010, 43, 10253-10261
49. (g), He, G.,;, Yan, N.,;, Yang, J.,;, Wang, H.,;, Ding, L.,;, Yin, S.,;, Fang, Y., Macromolecules, 2011, 44, 4759-4766
50. (h), Olley, D. A.,;, Wren, E. J.,;, Vamvounis, G.,;, Fernee, M. J.,;, Wang, X.,;, Burn, P. L.,;, Meredith, P.,;, Shaw, P. E., Chem. Mater. 2011, 23, 789-794
51. (i), Tang, G.,;, Chen, S. S. Y.,;, Shaw, P. E.,;, Hegedus, K.,;, Wang, X.,;, Burn, P. L.,;, Meredith, P., Polym. Chem. 2011, 2, 2360-2368.
52. (a), Thomas, S. W., III,;, Joly, G. D.,;, Swager, T. M., Chem. Rev. 2007, 107, 1339-1386
53. (b), Zahn, S.,;, Swager, T. M., Angew. Chem. Int. Ed. 2002, 41, 4225-4230
54. (c), Bunz, U. H. F., Chem. Rev. 2000, 100, 1605-1644.
55. (a), Qin, A.,;, Lam, J. W. Y.,;, Tang, B. Z., Macromolecules 2010, 43, 8693-8702
56. (b), Qin, A.,;, Lam, J. W. Y.,;, Tang, B. Z., Chem. Soc. Rev. 2010, 39, 2522-2544
57. (c), Liu, J.,;, Lam, J. W. Y.,;, Tang, B. Z., Chem. Rev. 2009, 109, 5799-5867
58. (d), Lam, J. W. Y.,;, Tang, B. Z., Acc. Chem. Res. 2005, 38, 745-754
59. (e), Häußler, M.,;, Tang, B. Z., Adv. Polym. Sci. 2007, 209, 1-58
60. (f), Lam, J. W. Y.,;, Tang, B. Z., J. Polym. Sci. Part A: Polym. Chem. 2003, 41, 2607-2629
61. (g), Liu, J.,;, Zhong, Y.,;, Lam, J. W. Y.,;, Lu, P.,;, Hong, Y.,;, Yu, Y.,;, Yue, Y.,;, Faisal, M.,;, Sung, H. H.-Y.,;, Williams, I.,;, Wong, K. S.,;, Tang, B. Z., Macromolecules 2010, 43, 4921-4936
62. (h), Wang, J.,;, Mei, J.,;, Yuan, W.,;, Lu, P.,;, Qin, A.,;, Sun, J.,;, Ma, Y.,;, Tang, B. Z., J. Mater. Chem. 2011, 21, 4056-4059
63. (i), Hu, R.,;, Maldonado, J. L.,;, Rodriguez, M.,;, Deng, C.,;, Jim, C. K. W.,;, Lam, J. W. Y.,;, Yuen, M. M. F.,;, Ramos-Ortiz, G.,;, Tang, B. Z., J. Mater. Chem. 2012, 22, 232-240.
64. (a), Liu, J.,;, Zhong, Y.,;, Lu, P.,;, Hong, Y.,;, Lam, J. W. Y.,;, Faisal, M.,;, Yu, Y.,;, Wong, K. S.,;, Tang, B. Z., Polym. Chem. 2010, 1, 426-429
65. (b), Lu, P.,;, Lam, J. W. Y.,;, Liu, J.,;, Jim, C. K. W.,;, Yuan, W.,;, Xie, N.,;, Zhong, Y.,;, Hu, Q.,;, Wong, K. S.,;, Cheuk, K. K. L.,;, Tang, B. Z., Macromol. Rapid Commun. 2010, 31, 834-839.
66. (a), Ojima, I., In The Chemistry Organic Silicone Compounds;, Patai, S., Rapoport, Z., Eds.; John Wiley: Chichester, UK, 1989; p 1479
67. (b), Marciniec, B., Comprehensive Handbook on Hydrosilylation; Pergamon Press: New York, 1992; pp 130-137
68. (c), Mori, A.,;, Takahisa, E.,;, Yaamamura, Y.,;, Kato, T.,;, Mudalige, A. P.,;, Kajiro, H.,;, Hirabayashi, K.,;, Nishihara, Y.,;, Hiyama, T., Organometallics 2004, 23, 1755-1765
69. (d), Perry, R. J.,;, Karageorgis, M.,;, Hensler, J., Macromolecules 2007, 40, 3929-3938.
70. (a), Ohshita, J.,;, Kunai, A., Acta Polym. 1998, 49, 379-403
71. (b), Kunai, A.,;, Toyoda, E.,;, Nagamoto, I.,;, Horio, T.,;, Ishikawa, M., Organometallics 1996, 15, 75-83
72. (c), Ohshita, J.,;, Kanaya, D.,;, Watanabe, T.,;, Ishikawa, M., J. Organomet. Chem. 1995, 489, 165-173
73. (d), Ohshita, J.,;, Matsuguchi, A.,;, Furumori, K.,;, Hong, R.-F.,;, Ishikawa, M., Macromolecules 1992, 25, 2134-2140
74. (e), Corriu, R. J. P.,;, Gerbler, P.,;, Guérin, C.,;, Henner, B. J. L.,;, Jean, A.,;, Mutin, P. H., Organometallics 1992, 11, 2507-2513
75. (f), Wu, H. J.,;, Interrante, L. V., Macromolecules 1992, 25, 1840-1841.
76. (a), Sohn, H.,;, Sailor, M. J.,;, Magde, D.,;, Trogler, W. C., J. Am. Chem. Soc. 2003, 125, 3821-3830
77. (b), Sanchez, J. C.,;, Trogler, W. C., Macromol. Chem. Phys. 2008, 209, 1527-1540
78. (c), Sanchez, J. C.,;, Trogler, W. C., J. Mater. Chem. 2008, 18, 3143-3156
79. (d), Sohn, H.,;, Calhoun, R. M.,;, Sailor, M. J.,;, Trogler, W. C., Angew. Chem. Int. Ed. 2001, 40, 2104-2105
80. (e), Sanchez, J. C.,;, DiPasquale, A. G.,;, Rheingold, A. L.,;, Trogler, W. C., Chem. Mater. 2007, 19, 6459-6470.
81. Osborn, J. A.,;, Jardine, F. H.,;, Young, J. F.,;, Wilkinson, G., J. Chem. Soc. A 1966, 1711-1732.
82. Lee, I.-S.,;, Kwak, Y.-W.,;, Kim, D.-H.,;, Cho, Y.,;, Ohshita, J., J. Organomet. Chem. 2008, 693, 3233-3239.
83. Lu, P.,;, Lam, J. W. Y.,;, Liu, J.,;, Jim, C. K. W.,;, Yuan, W.,;, Chan, C. Y. K.,;, Xie, N.,;, Hu, Q.,;, Cheuk, K. K. L.,;, Tang, B. Z., Macromolecules 2011, 44, 5977-5986.
84. Berlman, I. B., Handbook of Fluorescence Spectra of Aromatic Molecules; Academic Press: New York and London, 1971.
85. (a), Zhao, Z.,;, Lu, P.,;, Lam, J. W. Y.,;, Wang, Z.,;, Chan, C. Y. K.,;, Sung, H. H. Y.,;, Williams, I. D.,;, Ma, Y.,;, Tang, B. Z., Chem. Sci. 2011, 2, 672-675
86. (b), Zhao, Z.,;, Chen, S.,;, Deng, C.,;, Lam, J. W. Y.,;, Chan, C. Y. K.,;, Lu, P.,;, Wang, Z.,;, Hu, B.,;, Chen, X.,;, Lu, P.,;, Kwok, H. S.,;, Ma, Y.,;, Qiu, H.,;, Tang, B. Z., J. Mater. Chem. 2011, 21, 10949-10956.
87. (a), Akhavan, J., The Chemistry of Explosives; Royal Society of Chemistry: Cambridge, 2004
88. (b), Peng, Y.,;, Zhang, A.-J.,;, Dong, M.,;, Wang, Y.-W., Chem. Commun. 2011, 47, 4505-4507.