The study of chiral conjugated polymers

Acta Polymerica

Volumn 48, Issue 4, 1997, Pages 116-141

  Pu, L ^a,b  

^a NORTH DAKOTA STATE UNIVERSITY   (United States)

^b UNIVERSITY OF VIRGINIA   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

COMPOSITION EFFECTS; MOLECULAR STRUCTURE; OPTICAL PROPERTIES; PH EFFECTS; SOLVENTS; SYNTHESIS (CHEMICAL); THERMAL EFFECTS;

CHIRAL CONJUGATED POLYMERS; CHIRAL MAIN CHAIN; CHIRAL RECOGNITION PROPERTIES; CHIROPTICAL PROPERTIES;

AROMATIC POLYMERS;

EID: 0031117834     PISSN: 03237648     EISSN: None     Source Type: Journal    
DOI: 10.1002/actp.1997.010480402     Document Type: Article

References (146)

1. H. Shirakawa, E.J. Louis, A. G. MacDiarmid, C.K. Chiang, J. Heeger, J. Chem. Soc., Chem. Commun. 1977, 578.
2. Handbook oj'Conducting Polymers (Ed.: T. A. Skotheim), Marcel Dekker, New York 1986, Vols. 1 and 2.
3. J.L. Brédas, R. Silbey, Conjugated Polymers: The Novel Science and Technology of Highly Conducting and Nonlinear Optically Active Materials, Kluwer Academic, Boston 1991.
4. Conjugated Conducting Polymers (Ed.: H.G. Kiess), Springer, New York 1992.
5. M. Kanizidis, Chem. Eng. Ne\vs 1990, Dec, 36.
6. F. Ciardelli, E. Benedetti, O. Pieroni, Makromol. Chem. 1967, 103, 1.
7. F. Ciardelli, S. Lanzillo, O. Pieroni, Macromolecules 1974, 7,2.
8. T. Masuda, T. Higashimura, Adv. Polym. Sei. 1987, 81, 121.
9. C.I. Simionescu, V. Percée, Prog. Polym. Sei. 1982, 8 , 133.
10. T. Aoki, M. Kokai, K.-i. Shinohara, E. Oikawa, Chem. Lett. 1993, 2009.
11. T. Aoki, K.-I. Shinohara, T. Kaneko, E. Oikawa, Macromolecules 1996,29,4192.
12. E. Yashima, S. Huang, Y. Okamoto, J. Chem. Soc., Chem. Commun. 1994, 1811:
13. (a) E. Yashima, T. Matsushima, Y. Okamoto, J. Am. Chem. Soc. 1995,117,11596.
14. (b) E. Yoshima, T. Nimura, T. Matsushima, Y. Okamoto, J. Am. Chem. Soc. 1996,118, 9800.
15. Y. Kishimoto, M. Itou, T. Miyatake, T. Ikariya, R. Noyori, Macromolecules 1995,25, 6662.
16. M. Yamaguchi, K. Omata, M. Hirama, Chem. Lett. 1992,2261.
17. [ 16] T. Masuda, T. Hamano, K. Tsuchihara, T. Higashimura, Macromolecules 1990,23, 1374.
18. E.J. Ginsburg, C.B. German, S.R. Marder, R.H. Grubbs, J. Am. Chem. Soc. 1989,111,7621.
19. C.B. Gorman, E.J. Ginsburg, S.R. Marder, R.H. Grubbs, Ange\v. Chem. Adv. Mater. 1989,101, 1603.
20. J.S. Moore, C.B. Gorman, R.H. Grubbs, J. Am. Chem. Soc. 1991,113, 1704.
21. M. Lemaire, D. Delabouglise, R. Garreau, A. Guy, J. Roncali, J. Chem. Soc., Chem. Commun. 1988, 658.
22. (a) M. Lemaire, D. Delabouglise, R. Garreau, J. Roncali, J. Chim. Phys. 1989, 86, 193.
23. (b) M. Lemaire, R. Garreau, J. Roncali, D. Delabouglise, H.K.. Youssoufi, F. Gamier, Ne\v J. Chem. 1989,13, 863.
24. J. Roncali, R. Garreau, D. Delabouglise, F. Garnier, M. Lemaire, Makromol. Chem., Macromol. Symp. 1988,20/27,601.
25. D. Kotkar, V. Joshi, P.K. Ghosh, J. Chem. Soc., Chem. Commun. 1988, 917.
26. M. Andersson, P.O. Ekeblad, T. Hjertberg, O. Wennerström, O. Inganäs, Polym. Commun. 1991, 32, 546.
27. M.M. Bouman, E.W. Ueijer,Adv. Mater. 1995, 7, 385.
28. B.M.W. Langeveld-Voss, R.A.J. Janssen, M.P.T. Christiaans, S.C.J. Meskers, H.P.J.M. Dekkcrs, E.W. Meijer, J. Am. Cliem. Soc. 1996,7/5,4908.
29. R.L. Elsenbaumer, H. Eckhardt, Z. Iqbal, J. Toth, R.H. Baughman, Mol Cryst. Liq. Ctyst. 1985,118,111.
30. M. Salmon, G. Bidan, J. Electrochem. Soc. 1985,132,1897.
31. D. Delabouglise, F. Gamier, Syiith. Met. 1990,39, 117.
32. T. Kato, M. Gondaira, T. Amemiya, A. Fujishima, Chem. Lett. 1991,713.
33. C.J. Pickett, K.S. Ryder, J.-C. Moutet, J. Chem. Soc., Chem. Commun. 1992, 694.
34. C.J. Pickett, K.S. Ryder, J. Chem. Soc., Dalton Trans. 1994, 2181.
35. J.-C. Moutet, E. Saint-Aman, F. Tran-Van, P. Angibeaud, J.-P. Utille, Adv. Mater. 1992, 4, 511.
36. S. Li, W.C. Purdy, Chem. Rev. 1992, 92, 1457.
37. J.-C. Lepretre, E. Saint-Aman, J.-P. Utille, J. Electroanal. Chem. 1993, 347, 465.
38. G. Tourillon, F. Garnier,'J Electroanal. Chem. 1982,135, 173.
39. J. Bargon, S. Mohmand, R.J. Waltman, Mol. Cryst. Liq. Cryst. 1983, 93, 279.
40. S. Bruckenstein, J.W. Sharkey, J. Electroanal. Chem. 1988, 247,211.
41. P.A. Brass, U. Schöberl, J. Daub, Adv. Mater. 1991, 3, 198.
42. (a) Polydiacetylenes (Eds.: D. Bloor, R.R. Chance), Martinus Nijhoff, Dordrecht 1985.
43. (b) D. Bloor, in Developments in Crystalline Polymers (Ed.: D.C. Bassett), Applied Science, London 1982, p. 151.
44. (a) J. Zyss,.J. Mol. Electron. 1985, 7,25.
45. (b) K.C. Lim, M. Sinclair, S.A. Casalnuovo, C.R. Fincher, F. Wudl, A.J. Heeger, Mol. Cryst. Liq. Cryst. 1984, 705,329.
46. G. Wenz, M.A. Muller, M. Schmidt, G. Wegner, Macromolecules 1984,17, 837.
47. A.F. Drake, P. Udvarhelyi, D.J. Ando, D. Bloor, J.S. Obhi, S. Mann, Polymer 1989, 30, 1063.
48. E. Harlev, F. Wudl, "Synthesis and Optical Properties of Chiral Poly(2,5-bis(3,7-dimethyl-6-octenoxy)-l,4-phenylenevinylene)", in Conjugated Polymers and Related Materials, Tlie Interconnection of Chemical and Electronic Structure (Eds.: W.R. Salaneck, I. Lundström, B. Ranby),Proc. of the 81st Nobel Symp., Oxford University Press, Oxford 1993, p. 139.
49. Selected references on polyisocyanates: (a) A.J. Bur, L.J. Fetters, Chem. Rev. 1976, 76, 727.
50. (b) V.E. Shashoua, W. Sweeny, R.F. Tietz, J. Am. Chem. Soc. 1960, 82, 866.
51. For the synthesis of the first optically active polyisocyanate, see: M. Goodman, S.-C. Chen, Macromolecules 1970, 3, 398.
52. M.M. Green, R.A. Gross, C. Crosby III, R.C. Schilling, Macromolecules 1987, 20, 992.
53. (e) M.M. Green, R.A. Gross, R. Cook, R.C. Schilling, Macromolecules 1987, 20, 2638.
54. (f) M.M. Green, C. Andreola, B. Munoz, M.P. Reidy, K. Zero, J. Am. Chem. Soc. 1988, 770, 4063.
55. (g) M.M. Green, S. Lifson, A. Teramoto, Chirality 1991, 3, 285.
56. (h) M.M. Green, M.P. Reidy, R.J. Johnson, G. Darling, D.J. O'Leary, G. Willson, J. Am. Chem. Soc. 1989, 777, 6452.
57. S. Lifson, C.E. Felder, M.M. Green, Macromolecules 1992,25,4142.
58. (j) Y. Okamoto, M. Matsuda, T. Nakano, E. Yashima, Polym. J. 1993, 25, 391. (k) A photochemically induced M- and P-helical transition of a chiral polyisocyanate was reported: G. Maxein, R. Zentel, Macromolecules 1995, 28, 8438.
59. Selected references on polyisocyanides: (a) F. Millich, Chem. Rev. 1972, 72, 101.
60. (b) F. Millich, Adv. Polym. Sei. 1975, 19, 117.
61. F. Millich, Macromol. Rev. 1980, 75, 207.
62. R.J.M. Nolle, A.J.M. van Beijnen, W. Drenth, J. Am. Chem. Soc. 1974, 96, 5932.
63. (e) A.J.M. van Beijnen, R.J.M. Nolle, W. Drenth, A.M.F. Hezemans, Tetrahedron 1976,32,2017.
64. (f) P.C. Kamer, R.J.M. Nolle, W. DrcntM Am. Cliem. Soc. 1988,110, 6818.
65. (g) M.M. Green, R.A. Gross, EC. Schilling, K. Zero, C. Crosby 111, Macromolecules 1988,21,1839.
66. (h) C. Kollmar, R. Hoffmann, J. Am. Cliem. Soc. 1990, 112, 8230.
67. A preformed chiral oligomer template was observed to promote a screw-sense-selective polymerization of isocyanides: F. Takei, K. Yanai, K. Onitsuka, S. Takahashi, Ange\v. Client. Int. Ed. Engl. 1996, 55, 1554.
68. R.J.M. Nolle, Chem. Soc. Rev. 1994, 23, 11.
69. R.J.M. Nolle, W. Drenth, in Recent Advances in Mechanistic and Synthetic Aspects of Polymerization (Eds.: M. Fonlanille, A. Guyol), Reidel, Dordrecht 1987, p. 451.
70. T.J. Deming, B.M. Novak, J. Am. Chem. Soc. 1992, 114, 7926.
71. S. Lifson, C. Andreola, N.C. Peterson, M.M. Green, J. Am. Chem. Soc. 1989, 777, 8850.
72. M.M. Green, B.A. Garetz, B. Munoz, H.P. Chang, J. Am. Chem. Soc. 1995,777,4181.
73. M.M. Green, N.C. Peterson, T. Sato, A. Teramoto, R. Cook, S. Lifson, Science 1995,268, 1860.
74. M.M. Green, C. Andreola, B. Munoz, M.P. Reidy, K. Zero, J. Am. Chem. Soc. 1988, 770, 4063.
75. E. Ramos, J. Bosch, J.L. Serrano, T. Sierra, J. Veciana, J. Am. Chem. Soc. 1996,118, 4703.
76. R.D. Miller, J. MichI, Chem. Rev. 1989, 89, 1359.
77. H. Tachibana, M. Matsumoto, Y. Tokura, Y. Morilomo, A. Yamaguchi, S. Koshihara, R.D. Miller, S. Abe, Phys. Rev. B 1993,47,4363.
78. R. West, J. Maxka, in Inorganic and Organometallic Polymers (Eds.: M. Zeldin, K.J. Wynne, H.R. Allcock), ACS Symposium Series 360, American Chemical Society, Washington, DC 1988, Chap. 2.
79. (a) M. Fujiki,J.Am. Chem. Soc. 1994,770,6017.
80. (b) M. Fujiki, J. Am. Chem. Soc. 1994, 776, 11976.
81. H. Frey, M. Möller, K. Matyjaszewski, Macromolecules 1994, 27, 1814.
82. H. Frey, M. Möller, A. Turetskii, B. Lolz, K. Malyjaszewski, Macromolecules 1995, 28, 5498.
83. M.R. Majidi, L.A.P. Kane-Maguire, G.G. Wallace, Polymer 1994,35,3113.
84. (a) M.R. Majidi, L.A.P. Kane-Maguire, G.G. Wallace, Polymer 1995, 36, 3597.
85. (b) M.R. Majidi, L.A.P. Kane-Maguire, G.G. Wallace, Polymer 1996, 37, 359.
86. E.E. Havinga, M.M. Bouman, E.W. Meijer, A. Pomp, M.M.J. Simenon, Synth. Met. 1994, 66, 93.
87. E.P. Kyba, G.W. Gokel, F. de Jong, K. Koga, L.R. Sousa, M.G. Siegel, L. Kaplan, G.D.Y. Sogah, D.J. Cram, J. Org. Chem. 1977, 42, 4173.
88. (a) C. Rosini, L. Franzini, A. Raffaelli, P. Salvadorl, Synthesis 1992, 503. (b) J.K. Whilesell, Chem. Rev. 1989, 89, 1581.
89. G. Bringmann, R. Waller, R. Weirich, Ange\v. Chem. Int. Ed. Engl. 1990,29,977.
90. K. Narasaka, Synthesis 1991, 1.
91. Q.-S. Hu, D. Vitharana, L. Pu, Tetrahedron: Asymmetry 1995, 6, 2123.
92. Q.-S. Hu, D. Vitharana, G. Liu, V Jain, M.W. Wagaman, L. Zhang, T.R. Lee, L. Pu, Macromolecules 1996, 29, 1082.
93. Q.-S. Hu, D. Vitharana, L. Pu, m Electrical, Optical, and Magnetic Properties of Organic Solid State Materials HI (Eds.: A.K.-Y. Jen, C.Y.-C. Lee, L.R. Dalton, M.F. Rubner, G.E. Wnek, L.Y. Chiang), MRS, Pittsburgh 1996, p. 621.
94. J.Z. Zhang, M.A. Kreger, Q.-S. Hu, D. Vitharana, L. Pu, P.J. Brock, J.C. Scott, J. Chem. Phys. 1997, 706, 3710.
95. Q.-S. Hu, D. Vitharana, G. Liu, V Jain, L. Pu, Macromolecules 1996 29. 5075.
96. L. Ma, Q.-S. Hu, K. Musick, D. Vitharana, C. Wu, C.M.S. Kwan, L. Pu, Macromolecules 1996, 29, 5083.
97. L. Ma, Q.-S. Hu, L. Pu, Tetrahedron: Asymmetry 1996, 7, 3103.
98. H. Cheng, L. Ma, Q.-S. Hu, X.-F. Zheng, J. Anderson, L. Pu, Tetrahedron: Asymmetry 1996, 7, 3083.
99. G. Zotti, Synth. Met. 1992,51, 373.
100. (a) M.J. Marsella, P.J. Carroll, T.M. Swager, J. Am. Chem. Soc. 1995, 117, 9832.
101. (b) M.J. Marsella, R.J. Newland, P.J. Carroll, T.M. Swager, J. Ain. Chem. Soc. 1995,117, 9842.
102. M.J. Marsella, T.M. Swager, J. Ain. Chem. Soc. 1993, 115, 12214.
103. H.K. Youssoufi, A. Yassar, S. Baïteche, M. Hmyene, F. Garnier, Synth. Met. 1994, 67, 251.
104. Q. Zhou, T.M. Swager, J. Am. Chem. Soc. 1995, 777, 7017.
105. D.J. Cram, R.C. Helgeson, K. Koga, E.P. Kyba, K. Madan, L.R. Sousa, M. Siegel, P. Moreau, G. W. Gokel, J.M. Timko, G.D.Y. Sogah, J. Org. Chem. 1978, 43, 2758.
106. L. Pu et al., results to be published.
107. B.S. Kang, M.-L. Seo, Y.S. Jun, C.K. Lee, S.C. Shin, J. Chem. Soc., Chem. Commun. 1996, 1167.
108. G.G. Malliaras, J.K. Herrema, J. Wildeman, R.H. Wieringa, R.E. Gill, S.S. Lampoura, G. Hadziioannou, Adv. Mater. 1993,5,721.
109. R.E. Gill, G.G. Malliaras, J. Wildeman, G. Hadziioannou, Adv. Mater. 1994, 6, 132.
110. H.E. Katz, L. Torsi, A. Dodabalapur, Chem. Mater. 1995, 7, 2235.
111. M.R. Andersson, M. Berggren, O. Inganäs, G. Gustafsson, J.C. Gustafsson-Carlberg, D. Seise, T. Hjertberg, O. Wennerström, Macromolecules 1995, 28, 7525.
112. L. Ma, Q.-S. Hu, D. Vitharana, L. Pu, Polym. Prepr. 1996, 37(2), 462.
113. L. Ma, Q.-S. Hu, D. Vitharana, C. Wu, C.M.S. Kwan, L. Pu, Macromolecules 1997, 30, 204.
114. S.F. Mason, Molecular Optical Activity and the Chiral Discriminations, Cambridge University Press, New York 1982, p. 72.
115. J. Zyss, J. Chem. Phys. 1993, 98, 6583.
116. (a) J. Zyss, C. Dhenaut, T. Chauvan, I. Ledoux, Chem. Phys. Lett. 1993, 206, 409.
117. (b) I. Ledoux, J. Zyss, J.S. Siegel, J. Brienne, J.-M. Lehn, Chem. Phys. Lett. 1990, 772,440.
118. J. Zyss, I. Ledoux, Chem. Rev. 1994, 94, 77.
119. C. Dhenaut, I. Ledoux, I.D.W. Samuel, J. Zyss, M. Bourgault, H.L. Bozec, Nature 1995, 374, 339.
120. L. Ma, L. Pu, submitted.
121. Certain dipolar chromophores attached to the helical main chain of poly(isocyanide)s have shown enhanced secondorder NLO property: M. Kauranen, T. Verbiest, C. Boutton, M.N. Teerenstra, K. Clays, AJ. Scheuten, RJ.M. Nolle, A. Persoons, Science 1995, 270, 966.
122. Q.-S. Hu, X.-F. Zheng, L. Pu, J. Org. Chem. 1996, 61, 5200.
123. Q.-S. Hu, D. Vitharana, X.-F. Zheng, C. Wu, C.M.S. Kwan, L. Pu, J. Org. Chem. 1996, 61, 8370.
124. D. Vitharana, Q.-S. Hu, L. Pu, Polym. Prcpr. 1996, 37(1), 855.
125. B.C. Blossey, W.T. Ford, "Polymeric Reagents", in Comprehensive Polymer Science. The Synthesis, Characterization, Reactions and Applications of Polymers (Eds.: G. Allen, J. Bevington), Pergamon Press, New York 1989, Vol. 6, p. 81.
126. C.UJr. Pittman, "Polymer Supported Catalysts", in Comprehensive Organometallic Chemistry (Eds.:_G. Wilkinson, F.G.A. Stone, E.W. Abel), Pergamon Press, Oxford 1983, Vol. 8, p. 553.
127. W.-S. Huang, Q.-S. Hu, X.-S. Cheng, J. Andersen, L. Pu, J. Am. Client. Soc. 1997, in press.
128. 2Zn catalyzed by chiral arnino alcohols, see: K. Soai, S. Niwa, Client. Rev. 1992, 92, 833.
129. V.R.C. Schulz, R.H. Jung, Makromol. Ghent. 1968,116, 190.
130. (a) C.G. Overberger, T. Yoshimura, A. Ohnishi, A.S. Gomes, J. Polym. Sei. Polym. Client. Ed. A 1970, 8, 2275.
131. (b) C.G. Overberger, A. Ohnishi, A.S. Gomes, J. Polym. Sei. Polym. Chem. Ed. A 1971, 9, 1139.
132. Y. Tamai, Y. Matsuzaka, S. Ôi, S. Miyano, Bull. Cltem. Soc. Jpn. 1991, 64, 2260.
133. Q. Mi, L. Gao, M. Ding, Macmmoleailes 1996,29, 5758.
134. P.V. Bedworth, J.M. Tour, Macromolecules 1994, 27, 622.
135. (a) S. Anderson, U. Neidlein, V Grämlich, F. Diederich, Ange\v. Chem. Int. Ed. Engl. 1995, 34, 1596.
136. (b) U. Neidlein, F. Diederich, Chem. Soc., Client. Commun. 1996, 1493.
137. M.-K. Ng, H.-F. Chow, T.-L. Chan, T.C.VV. Mak, Tetrahedron Lett. 1996,37, 2979.
138. H.-F. Chow, M.-K. Ng, Tetrahedron: Asymmetry 1996, 7, 2251.
139. (a) Y. Ito, E. Ihara, M. Murakami, Angm: Client. Int. Ed. Engl. 1992, 31, 1509.
140. (b) Y. Ito, E. Ihara, M. Murakami, M. Sisido, Macromolecules 1993, 25, 6810.
141. P. Magnus, W. Danikiewicz, T. Katoh, J. C. Huffman, K. Foiling, J. Am. Chem. Soc. 1990,112, 2465.
142. J. Huber, R. Fiesel, U. Scherf, Polym. Prepr. 1996, 37,440.
143. R. Fiesel, J. Huber, U. Scherf, Angew: Chem. Int. Ed. Engl. 1996,55,2111.
144. Y. Dai, T.J. Katz, D.A. Nichols, Angew. Chem. Int. Ed. Engl. 1996,35,2109.
145. (a) A. Sudhakar, T.J. Katz, B.-W. Yang, J. Am. Chem. Soc. 1986, 108, 2790.
146. (b) T.J. Katz, A. Sudhakar, M.F. Teasley, A.M. Gilbert, W.E. Geiger, M.P. Robben, M. Wuensch, M.D. Ward, J. Am. Chem. Soc. 1993, 7/5, 3182.