Thiol-Yne click polymerization: Regio- and stereoselective synthesis of sulfur-rich acetylenic polymers with controllable chain conformations and tunable optical properties

Macromolecules

Volumn 44, Issue 1, 2011, Pages 68-79

  Liu, Jianzhao ^a,c   Lam, Jacky W Y ^a,c   Jim, Cathy K W ^a,c   Ng, Jason C Y ^a   Shi, Jianbing ^a   Su, Huimin ^b   Yeung, Kwok Fai ^b   Hong, Yuning ^a,c   Faisal, Mahtab ^a,c   Yu, Yong ^a,c   Wong, Kam Sing ^b   Tang, Ben Zhong ^a,c,d  

^a HONG KONG UNIVERSITY OF SCIENCE AND TECHNOLOGY   (China)

^b Institute of Molecular Functional Materials   (Hong Kong)

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

^d ZHEJIANG UNIVERSITY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

ACETYLENE; IRRADIATION; LIGHT REFRACTION; ORGANIC SOLVENTS; POLYMERIZATION; REFRACTIVE INDEX; REFRACTOMETERS; RHODIUM; RHODIUM COMPOUNDS; STEREOSELECTIVITY; SULFUR;

CERAMIZATION; CHAIN CONFORMATIONS; DITHIOLS; E-CONTENT; ENGINEERING CONTROLS; ENHANCED EMISSION; FILM-FORMING; HIGH MOLECULAR WEIGHT; HIGH REFRACTIVE INDEX; HIGH YIELD; LIGHT IRRADIATIONS; OPTICAL DISPERSION; OPTICAL LIMITING; OPTICAL TRANSPARENCY; PHOTOPATTERNS; POLYMERIZATION PROCESS; REGIO-SELECTIVE; RHODIUM COMPLEXES; ROOM TEMPERATURE; SEMI-CONDUCTING NANOPARTICLES; SEQUENTIAL ADDITION; STEREOSELECTIVE SYNTHESIS; TELECOM; UV CURABLE; UV IRRADIATION;

POLYMERS;

EID: 78650864060     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma1023473     Document Type: Article

References (104)

1. Grimsdale, A. C.; Chan, K. L.; Martin, R. E.; Jokisz, P. G.; Holmes, A. B. Chem. Rev. 2009, 109, 897
2. Lo, S. C.; Burn, P. L. Chem. Rev. 2007, 107, 1097
3. 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 1999, 397, 121
4. Cheng, Y. J.; Yang, S. H.; Hsu, C. S. Chem. Rev. 2009, 109, 5868
5. Dennler, G.; Scharber, M. C.; Brabec, C. J. Adv. Mater. 2009, 21, 1323
6. Chen, L. M.; Hong, Z. R.; Li, G.; Yang, Y. Adv. Mater. 2009, 21, 1434
7. Gunes, S.; Neugebauer, H.; Sariciftci, N. S. Chem. Rev. 2007, 107, 1324
8. Thompson, B. C.; Frechét, J. M. J. Angew. Chem., Int. Ed. 2008, 47, 58
9. Allard, S.; Forster, M.; Souharce, B.; Thiem, H.; Scherf, U. Angew. Chem., Int. Ed. 2008, 47, 4070
10. Murphy, A. R.; Frechét, J. M. J. Chem. Rev. 2007, 107, 1066
11. Shirakara, H. Angew. Chem., Int. Ed. 2001, 40, 2575
12. MacDiarmid, A. G. Angew. Chem., Int. Ed. 2001, 40, 2581
13. Heeger, A. J. Angew. Chem., Int. Ed. 2001, 40, 2591
14. Liu, J.; Lam, J. W. Y.; Tang, B. Z. Chem. Rev. 2009, 109, 5799
15. Akagi, K. Chem. Rev. 2009, 109, 5354
16. Masuda, T. J. Polym. Sci., Part A: Polym. Chem. 2007, 45, 165
17. Lam, J. W. Y.; Tang, B. Z. Acc. Chem. Res. 2005, 38, 745
18. Simionescu, C. I.; Percec, V. Prog. Polym. Sci. 1982, 8, 133
19. Nielsen, M. B.; Diederich, F. Chem. Rev. 2005, 105, 1837
20. Diederich, F. Nature 1994, 369, 199
21. Diederich, F.; Kivala, M. Adv. Mater. 2010, 22, 803
22. Schmaltz, B.; Weil, T.; Mullen, K. Adv. Mater. 2009, 21, 1067
23. Wu, J.; Pisula, W.; Mullen, K. Chem. Rev. 2007, 107, 718
24. Cianga, I.; Yagci, Y. Prog. Polym. Sci. 2004, 29, 387
25. Scherf, U.; List, E. J. W. Adv. Mater. 2002, 14, 477
26. Bunz, H. F. Acc. Chem. Res. 2001, 34, 998
27. Thomas, S. W.; Joly, G. D.; Swager, T. Chem. Rev. 2007, 107, 1339
28. Morisaki, Y.; Chujo, Y. Prog. Polym. Sci. 2008, 33, 346
29. Ma, W.; Yang, C.; Gong, X.; Lee, K.; Heeger, A. J. Adv. Funct. Mater. 2005, 15, 1617
30. Li, G.; Shrotriya, V.; Huang, J.; Yao, Y.; Moriarty, T.; Emery, K.; Yang, Y. Nat. Mater. 2005, 4, 864
31. Kim, Y.; Cook, S.; Tuladhar, S. M.; Choulis, S. A.; Nelson, J.; Durrant, J. R.; Bradley, D. D. C.; Giles, M.; McCulloch, I.; Ha, C. S.; Ree, M. Nat. Mater. 2006, 5, 197
32. Park, S. H.; Roy, A.; Beaupre, S.; Cho, S.; Coates, N.; Moon, J. S.; Moses, D.; Leclerc, M.; Lee, K.; Heeger, A. J. Nature Photon 2009, 3, 297
33. Gies, A. P.; Geibel, J. F.; Hercules, D. M. Macromolecules 2010, 43, 943
34. Cebe, P. Polym Polym. Compos. 1995, 3, 239
35. Edmonds, J. T.; Hill, H. W. (Phillips Petroleum Co.). U.S. Patent 3,354,129, 1967.
36. Perng, L. H. Polym. Degrad. Stab. 2000, 69, 323
37. Piaggio, P.; Giribone, D.; Musso, G. F.; Cuniberti, C.; Dellepiane, G.; Borghesi, A. Synth. Met. 1991, 41, 1359
38. Truce, W. E.; Simms, J. A. J. Am. Chem. Soc. 1956, 12, 2756
39. Griesbaum, K. Angew. Chem., Int. Ed. 1970, 9, 273
40. Patai, S. In The Chemistry of the Thiol Group; Wiley: London, 1974; Vol. 2.
41. Ananikov, V. P.; Malyshev, D. A.; Beletskaya, I. P.; Aleksandrov, G. G.; Eremenko, I. L. Adv. Synth. Catal. 2005, 347, 1993
42. Ichinose, Y.; Wakamatsu, K.; Nozaki, K.; Birbaum, J. L.; Oshima, K.; Utimata, K. Chem. Lett. 1987, 1671
43. MaDonald, J. W.; Corbin, J. L.; Newton, W. E. Inorg. Chem. 1976, 15, 9
44. Kuniyasu, H.; Ogawa, A.; Sato, K. I.; Ryu, I.; Kambe, N.; Sonoda, N. J. Am. Chem. Soc. 1992, 114, 5902
45. Bäckvall, J. E.; Ericcson, A. J. Org. Chem. 1994, 59, 5850
46. Han, L. B.; Zhang, C.; Yazawa, H.; Shimada, S. J. Am. Chem. Soc. 2004, 126, 5080
47. Ogawa, A.; Ikeda, T.; Kimura, K.; Hirao, T. J. Am. Chem. Soc. 1999, 121, 5108
48. Burling, S.; Field, L. D.; Messerle, B. A.; Vuong, K. Q.; Turner, P. J. Chem. Soc., Dalton Trans. 2003, 4181
49. Munro-Leighton, C.; Delp, S. A.; Alsop, N. M.; Blue, E. D.; Gunnoe, T. B. Chem. Commun. 2008, 111
50. Cao, C.; Fraser, L. R.; Love, J. A. J. Am. Chem. Soc. 2005, 127, 17614
51. Kondoh, A.; Yorimitsu, H.; Oshima, K. Org. Lett. 2008, 9, 1383
52. Malyshev, D. A.; Scott, N. M.; Marion, N.; Stevens, E. D.; Ananikov, V. P.; Beleskaya, I. P.; Nolan, S. P. Organometallics 2006, 25, 5562
53. Sabarre, A.; Love, J. A. Org. Lett. 2008, 10, 3941
54. Cao, C.; Wang, T.; Patrick, B. O.; Love, J. A. Organometallic 2006, 25, 1321
55. Ananikov, V. P.; Gayduk, K. A.; Orlov, N. V.; Beletskaya, I. P.; Khrustalev, V. N.; Antipin, M. Y. Chem.-Eur. J. 2010, 16, 2063
56. Häuller, M.; Tang, B. Z. Adv. Polym. Sci. 2007, 209, 1
57. Häuller, M.; Qin, A.; Tang, B. Z. Polymer 2007, 48, 6181
58. Qin, A.; Lam, J. W. Y.; Tang, B. Z. Chem. Soc. Rev. 2010, 39, 2522
59. Qin, A.; Lam, J. W. Y.; Tang, B. Z. Macromolecules 2010, 43, 8693
60. Iha, R. K.; Wooley, K. L.; Nystrom, A. M.; Burke, D. J.; Kade, M. J.; Hawker, C. J. Chem. Rev. 2009, 109, 5620
61. Hoyle, C. E.; Bowman, C. N. Angew. Chem., Int. Ed. 2010, 49, 1540
62. Lower, A. B. Polym. Chem. 2010, 1, 17
63. Sumerlin, B. S.; Vogt, A. P. Macromolecules 2010, 43, 1
64. Rim, C.; Son, D. Y. Tetrahedron Lett. 2009, 50, 4161
65. Lowe, A. B.; Hoyle, C. E.; Bowman, C. N. J. Mater. Chem. 2010, 20, 4745
66. Hoogenboom, R. Angew. Chem., Int. Ed. 2010, 49, 3415
67. Fairbanks, B. D.; Scott, T. F.; Kloxin, C. J.; Anseth, K. S.; Bowman, C. N. Macromolecules 2009, 42, 211
68. Chen, G.; Kumar, J.; Gregory, A.; Stenzel, M. H. Chem. Commun. 2009, 6291
69. Konkolewicz, D.; Gray-Weale, A.; Perrier, S. J. Am. Chem. Soc. 2009, 131, 18075
70. Chan, J. W.; Hoyle, C. E.; Lowe, A. B. J. Am. Chem. Soc. 2009, 131, 5751
71. Hensarling, R. M.; Doughty., V. A.; Chan, J. W.; Patton, D. L. J. Am. Chem. Soc. 2009, 131, 14673
72. Liu, J.; Zheng, R.; Tang, Y.; Häussler, M.; Lam, J. W. Y.; Qin, A.; Ye, M.; Hong, Y.; Gao, P.; Tang, B. Z. Macromolecules 2007, 40, 7473
73. Liu, J.; Zhang, L.; Lam, J. W. Y.; Jim, C. K. W.; Yue, Y.; Deng, R.; Hong, Y.; Qin, A.; Sung, H. H. Y.; Williams, I. D.; Jia, G. C.; Tang, B. Z. Macromolecules 2009, 42, 7367
74. Liu, J.; Zhong, Y.; Lam, J. W. Y.; Lu, P.; Hong, Y.; Yu, Y.; Yue, Y.; Faisal, M.; Sung, H. H. Y.; Williams, I. D.; Wong, K. S.; Tang, B. Z. Macromolecules 2010, 43, 4921
75. Shi, J. B.; Tong, B.; Li, Z.; Shen, J. B.; Zhao, W.; Fu, H. H.; Zhi, J.; Dong, Y. P.; Häussler, M.; Lam, J. W. Y.; Tang, B. Z. Macromolecules 2007, 40, 8195
76. Waldeck, D. H. Chem. Rev. 1991, 91, 415
77. Jiang, C.; Xie, R.; Li, F.; Allen, R. E. Chem. Phys. Lett. 2009, 474, 263
78. Sudesh Kumar, G.; Neckers, D. C. Chem. Rev. 1989, 89, 1915
79. Xie, S.; Natansohn, A.; Rochon, P. Chem. Mater. 1993, 5, 403
80. Häussler, M.; Liu, J.; Zheng, R.; Lam, J. W. Y.; Qin, A.; Tang, B. Z. Macromolecules 2007, 40, 1914
81. Peng, H.; Cheng, L.; Luo, J. D.; Xu, K. T.; Sun, Q. H.; Dong, Y. P.; Salhi, F.; Lee, P. P. S.; Chen, J. W.; Tang, B. Z. Macromolecules 2002, 35, 5349
82. Tang, B. Z.; Xu, H. Macromolecules 1999, 32, 2569
83. Yuan, W.; Sun, J. Z.; Liu, J. Z.; Dong, Y.; Li, Z.; Xu, H.; Qin, A.; Häussler, M.; Jin, J.; Zheng, Q.; Tang, B. Z. J. Phys. Chem. B. 2008, 112, 8896
84. Tutt, L. W.; Kost, A. Nature 1992, 356, 225
85. Hong, Y.; Lam, J. W. Y.; Tang, B. Z. Chem. Commun. 2009, 4332
86. Liu, J.; Lam, J. W. Y.; Tang, B. Z. J. Inorg. Organomet. Polym. Mater. 2009, 19, 249
87. Campbell, L.; Sharp, D. N.; Harrison, M. T.; Denning, R. G.; Turberfield, A. J. Nature 2000, 404, 53
88. Kim, J. M. Macromol. Rapid Commun. 2007, 28, 1191
89. Liu, J.; Ueda, M. J. Mater. Chem. 2009, 19, 8907 and references therein.
90. You, N.; Chueh, C.; Liu, C.; Ueda, M.; Chen, W. C. Macromolecules 2009, 42, 4456
91. Seferis, J. C. In Polymer Handbook, 3 rd ed.; Brandrup, J.; Immergut, E. H., Eds.; Wiley: New York, 1989; pp VI/451- VI/461.
92. Moshrefzadeh, R. S.; Misemer, D. K.; Radcliffe, M. D.; Francis, C. V.; Mohapatra, S. K. Appl. Phys. Lett. 1993, 62, 16
93. Tanio, N.; Irie, M. Jpn. J. Appl. Phys. 1994, 33, 3942
94. Irie, M.; Sakemura, K.; Okinaka, M.; Uchida, K. J. Org. Chem. 1995, 60, 8305
95. Hanazawa, M.; Sumiya, R.; Horika, Y.; Irie, M. J. Chem. Soc. Chem. Commun. 1992, 206
96. Griesser, T.; Hofler, T.; Jakopic, G.; Belzik, M.; Kern, W.; Trimmel, G. J. Mater. Chem. 2009, 19, 4557
97. Hecht, E. Optics, 4 th ed.; Addison Wesley: San Francisco, CA, 2002.
98. Yang, C. J.; Jenekhe, S. A. Chem. Mater. 1994, 6, 196
99. Kim, D. Y.; Sundheimer, M.; Otomo, A.; Stegman, G. I.; Winfried, H. G. H.; Mohlhaupt, G. R. Appl. Phys. Lett. 1993, 63, 290
100. Dislich, H. Angew. Chem., Int. Ed. 1979, 18, 49
101. Osborn, J. A.; Jardine, F. H.; Young, J. F.; Wilkinson, G. J. Chem. Soc. A 1966, 1711
102. Tang, B. Z.; Poon, W. H.; Leung, S. M.; Leung, W. H.; Peng, H. Macromolecules 1997, 30, 2209 and references therein.
103. Schrock, R. R.; Osborn, J. A. J. Am. Chem. Soc. 1976, 98, 2134
104. Yin, S.; Xu, H.; Su, X.; Li, G.; Song, Y.; Lam, J. W. Y.; Tang, B. Z. J. Polym. Sci., Part A: Polym. Chem. 2006, 44, 2346