The Heck polycondensation for functional polymers

Synlett

Volumn , Issue 18, 2006, Pages 2879-2893

  Lee, Youngu ^a   Liang, Yongye ^a   Yu, Luping ^a  

^a UNIVERSITY OF CHICAGO   (United States)

Author keywords

Complexes; Conjugation; Heck reaction; Palladium; Polymers

Indexed keywords

METALLOPORPHYRIN; PALLADIUM COMPLEX; POLY (4 PHENYLENEVINYLENE) DERIVATIVE; POLYVINYL DERIVATIVE; RUTHENIUM COMPLEX; UNCLASSIFIED DRUG;

CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CHROMATOPHORE; COMPLEX FORMATION; CRYSTALLIZATION; HECK REACTION; INFRARED SPECTROSCOPY; LIGHT REFRACTION; LIQUID CRYSTAL; OPTICAL ROTATION; PHYSICAL CHEMISTRY; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; REVIEW; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 33751289179     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2006-951526     Document Type: Review

References (89)

1. (a) Handbook of Conductive Polymers; Skotheim, T. A., Ed.; Marcel Dekker, Inc.: Basel, 1989.
2. (b) Reynolds, J. R.; Pomerantz, M. In Electroresponsive Molecular and Polymeric Systems, Vol. 2; Skotheim, T. A., Ed.; Marcel Dekker Inc.: Basel, 1991, Chap. 4.
3. (c) Segura, J. L. Acta. Polym. 1998, 49, 319.
4. Kaino, T.; Kubodera, K. I.; Tomura, S.; Kurihara, T.; Saito, S.; Tsutsui, T.; Tokito, S. Electron Lett. 1987, 23, 1095.
5. (a) Burroughes, J. H.; Bradley, D. D.; Brown, A. R.; Marks, R. N.; Mackay, K.; Friend, R. H.; Burns, P. L.; Holmes, A. B. Nature (London) 1990, 347, 539.
6. (b) Greiner, A. Polym. Adv. Technol. 1998, 9, 371.
7. (c) Kraft, A.; Grimdale, A. C.; Holmes, A. B. Angew. Chem. Int. Ed. 1998, 37, 402.
8. (d) Dai, L.; Winkler, B.; Dong, L.; Tong, L.; Mau, A. M. H. Adv. Mater. 2001, 13, 915.
9. Mcdonald, R. N.; Campbell, T. N. J. Am. Chem. Soc. 1960, 82, 4669.
10. Rajaraman, L.; Balasubramanian, M.; Nanjan, M. J. Curr. Sci. 1980, 49, 101.
11. Gilch, H. G.; Wheelwright, W. L. J. Polym. Sci., Part A1 1966, 4, 1337.
12. (a) Issaris, A.; Vanderzande, D.; Adriaensens, P.; Gelan, J. Macromolecules 1998, 31, 4426.
13. (b) Issaris, A.; Vanderzande, D.; Gelan, J. Polymer 1997, 38, 2571.
14. Staring, E. G.; Braun, D.; Rikken, G. L. J. A.; Demandt, R. J. C. E.; Kessener, Y. A. R. R.; Bruwmans, M.; Broer, D. Synth Met. 1994, 67, 71.
15. Chang, W.-P.; Whang, W.-T.; Lin, P.-W. Polymer 1996, 37, 1513.
16. (a) Wessling, R. A. J. Polym. Sci. Polym. Symp. 1985, 72, 55.
17. (b) Cho, B. R. Prog. Polym. Sci. 2002, 27, 307.
18. Conticello, V. P.; Gin, D. L.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 9708.
19. (a) Murase, I.; Ohnish, T.; Noguchi, T.; Hirooka, M. Polym. Commun. 1984, 25, 293.
20. (b) Tokito, S.; Tsutsui, T.; Saito, S. Polym. Commun. 1986, 27, 333.
21. (a) Heck, R. F.; Nolley, J. P. Jr. J. Org. Chem. 1972, 37, 2320.
22. (b) Dieck, H. A.; Heck, R. F. J. Org. Chem. 1975, 40, 1083.
23. (c) Heck, R. F. Acc. Chem. Res. 1979, 12, 146.
24. (d) Tao, W.; Silverberg, L. J.; Rheingold, A. L.; Heck, R. F. Organometallics 1989, 8, 2550.
25. (a) Heitz, W.; Brugging, W.; Freund, L.; Gailberger, M.; Greiner, A.; Jung, H.; Kampschulte, U.; Niebner, N.; Osan, F.; Schmidt, H. W.; Wicker, M. Makromol. Chem. 1988, 189, 119.
26. (b) Greiner, A.; Heitz, W. Makromol. Chem. Rapid. Commun. 1988, 9, 581.
27. (c) Suzuki, M.; Lim, J. C.; Saegusa, T. Macromolecules 1990, 23, 1574.
28. (d) Weitzel, H. P.; Mullen, K. Makromol. Chem. 1990, 191, 2837.
29. (e) Martelock, H.; Greiner, A.; Heitz, W. Makromol. Chem. 1991, 192, 967.
30. (f) Greiner, A.; Martelock, H.; Heitz, W. Synth. Met. 1991, 41-43, 881.
31. Bao, Z.; Chan, W. K.; Yu, L. Chem. Mater. 1993, 5, 2.
32. Lenz, R. W.; Han, C. C.; Lux, M. Polymer 1989, 30, 1041.
33. Chan, W. K.; Yu, L. Macromolecules 1995, 28, 6410.
34. Pan, M.; Bao, Z.; Yu, L. Macromolecules 1995, 28, 5151.
35. The Porphyrin, Vol. 5; Dolphin, D., Ed.; Academic Press: New York, 1978.
36. (a) Bao, Z.; Chen, Y.; Yu, L. Macromolecules 1994, 27, 4629.
37. (b) Wang, Q.; Wang, L.; Yu, J.; Yu, L. Adv Mater. 2000, 12, 974.
38. (c) You, W.; Wang, L.; Wang, Q.; Yu, L. Macromolecules 2002, 35, 4636.
39. (a) Balzani, V.; Scandola, F. Supramolecular Photochemistry; Horwood: Chichester, 1991.
40. (b) Juris, A.; Balzani, V.; Brigelletti, F.; Campagna, S.; Belster, P.; Von Zelewaky, A. Coord Chem. Rev. 1988, 84, 85.
41. (a) Meyer, T. J. Acc. Chem. Res. 1989, 22, 163.
42. (b) Yamamoto, T.; Yoneda, Y.; Maruyama, T. J. Chem. Soc., Chem. Commun. 1992, 1652.
43. (c) Yu, S. Z.; Hou, S.; Chan, W. K. Macromolecules 2000, 33, 3259.
44. (d) Lee, J.-K.; Yoo, D.; Rubner, M. F. Chem. Mater. 1997, 9, 1710.
45. (e) Grigg, R.; Holmes, J. M.; Jones, S. K.; Norbert, W. D. J. Chem. Soc., Chem. Commun. 1994, 185.
46. (a) Peng, Z.; Yu, L. J. Am. Chem. Soc. 1996, 118, 3777.
47. (b) Peng, Z.; Gharavi, A. R.; Yu, L. J. Am. Chem. Soc. 1997, 119, 4622.
48. (c) Wang, Q.; Wang, L.; Yu, L. J. Am. Chem. Soc. 1998, 120, 12860.
49. (d) Wang, Q.; Yu, L. J. Am. Chem. Soc. 2000, 122, 11806.
50. (a) Block Copolymers; Aggarwal, S., Ed.; Plenum Press: New York, 1970.
51. (b) Bates, F. S.; Fredrickson, G. H. Annu. Rev. 1990, 42, 525.
52. (c) Zhang, L.; Eisenberg, A. Science 1995, 268, 1728.
53. (d) Ruokolainen, J.; Makinen, R.; Torkkeli, M.; MaKeIa, T.; Serimaa, R.; Brinke, G. T.; Ikkala, O. Science 1998, 280, 557.
54. (e) Cornelissen, J. J. L. M.; Fischer, M.; Sommerdijk, N. A. J. M.; Nolle, R. J. M. Science 1998, 280, 1427.
55. (f) Massey, J.; Power, N. K.; Manners, I.; Winnik, M. A. J. Am. Chem. Soc. 1998, 120, 9533.
56. (a) Henglein, A. Top. Curr. Chem. 1988, 143, 115.
57. (b) Steigerwald, M. L.; Brus, L. E. Annu. Rev. Mater. Sci. 1989, 19, 471.
58. (c) Wang, Y.; Herron, N. J. Phys. Chem. 1991, 95, 525.
59. Maddux, T. M.; Li, W.; Yu, L. J. Am. Chem. Soc. 1997, 119, 844.
60. (a) Issberner, J.; Moors, R.; Vögtle, F. Angew. Chem., Int. Ed. Engl. 1994, 33, 2413.
61. (b) Tomalia, D. A. Adv. Mater. 1994, 6, 529.
62. Lansky, A.; Reiser, O.; De Meijere, A. Synlett 1990, 405.
63. Deb, S. K.; Maddux, T. M.; Yu, L. J. Am. Chem. Soc. 1997, 119, 9079.
64. (a) Li, W.; Wang, H.; Yu, L.; Morkved, T. L.; Jaeger, H. M. Macromolecules 1999, 32, 3034.
65. (b) Wang, H.; Wang, H. H.; Urban, V. S.; Littrell, K. C.; Thiyagarajan, P.; Yu, L. J. Am. Chem. Soc. 2000, 122, 6855.
66. (c) Wang, H.; Ng, M.-K.; Wang, L.; Yu, L.; Lin, B.; Meron, M.; Xiao, Y. Chem. Eur. J. 2002, 8, 3246.
67. (a) Ulman, A. An Introduction to Ultrathin Organic Films: From Langmuir-Blodgett to Self-Assembly; Academic Press: Boston, 1991.
68. (b) Decher, G.; Schlenoff, J. B. Multilayer Thin Films; VCH: Weinheim, 2003.
69. (a) Gaines, G. L. Insoluble Monolayers at Liquid-Gas Interfaces; Interscience: New York, 1966.
70. (b) Esker, A. R.; Mengel, C.; Wegner, G. Science 1998, 280, 892.
71. (c) Vierheller, T. R.; Foster, M. D.; Schmidt, A.; Mathauer, K.; Knoll, W.; Wegner, G.; Satija, S.; Majkrzak, C. F. Macromolecules 1994, 27, 6893.
72. (d) Hickel, W.; Duda, G.; Jurich, M.; Krohl, T.; Rochford, K.; Stegeman, G. I.; Swalen, J. D.; Wegner, G.; Knoll, W. Langmuir 1990, 6, 1403.
73. (a) Stockton, W. B.; Rubner, M. F. Macromolecules 1997, 30, 2717.
74. (b) Sukhishvili, S.; Granick, S. J. Am. Chem. Soc. 2000, 122, 9550.
75. (c) Fu, Y.; Chen, H.; Qiu, D.; Wang, Z.; Zhang, X. Langmuir 2002, 18, 4989.
76. (d) Cho, J.; Caruso, F. Macromolecules 2003, 36, 2845.
77. (a) Lehn, J.-M. In Supramolecular Chemistry; VCH: Weinheim, 1995.
78. (b) Decher, G. Science 1997, 277, 1232.
79. (c) Ho, P. K. H.; Kim, J.-S.; Burroughes, J. H.; Becker, H.; Li, S. F. Y.; Brown, T. M.; Cacialli, F.; Friend, R. H. Nature (London) 2000, 404, 481.
80. (d) Yang, S. Y.; Rubner, M. F. J. Am. Chem. Soc. 2002, 124, 2100.
81. (a) Schnolzer, M.; Kent, S. B. H. Science 1992, 256, 221.
82. (b) Dawson, P. E.; Muir, T. W.; Clark-Lewis, I.; Kent, S. B. H. Science 1994, 266, 776.
83. (c) Zhang, L.; Tam, J. P. J. Am. Chem. Soc. 1997, 119, 2363.
84. (d) Lemieux, G. A.; Bertozzi, C. R. Trends Biotechnol. 1998, 16, 506.
85. (e) Ni, Q.; Yu, L. J. Am. Chem. Soc. 1998, 120, 1645.
86. (a) Shiratori, S. S.; Rubner, M. F. Macromolecules 2000, 33, 4213.
87. (b) Park, S. Y.; Barrett, C. J.; Rubner, M. F.; Mayes, A. M. Macromolecules 2001, 34, 3384.
88. (a) Chan, E. W.; Lee, D.-C.; Ng, M.-K.; Wu, G.; Lee, K. Y. C.; Yu, L. J. Am. Chem. Soc. 2002, 124, 12238.
89. (b) Lee, D.-C.; Chang, B.-J.; Morales, G. M.; Jang, Y.-A.; Ng, M.-K.; Heller, S. T.; Yu, L. Macromolecules 2004, 37, 1849.