Poly(trimethylsilylcyclooctatetraene): A soluble conjugated polyacetylene via olefin metathesis

Journal of the American Chemical Society

Volumn 111, Issue 19, 1989, Pages 7621-7622

  Ginsburg, Eric J ^a   Gorman, Christopher B ^a   Grubbs, Robert H ^a   Marder, Seth R ^b  

^a CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

^b CALIFORNIA INSTITUTE OF TECHNOLOGY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000068914     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja00201a057     Document Type: Article

References (17)

1. See discussions in: (a) Handbook of Conducting Polymers', Skotheim, T. A., Ed.; Marcel Dekker: New York, 1986; two volumes. (b) Electroresponsive Molecular and Polymeric Systems; Skotheim, T. A., Ed.; Marcel Dekker: New York, 1988; Vol. 1.
2. See, for example: (a) Jen, K. Y.; Oboodi, R. L.; Elsenbaumer, R. L. Polym. Mat. Sci. Eng. 1985, 53, 79. (b) Hotta, S.; Rughooputh, S. D. D. V.; Heeger, A. J.; Wudl, F. Macromolecules 1987, 20, 212. (c) Rughooputh, S. D. D. V.; Nowak, M.; Hotta, S.; Heeger, A. J.; Wudl, F. Synthetic Metals 1987, 21, 41. (d) Askari, S. H.; Rughooputh, S. D.; Wudl, F.; Heeger, A. J. Polym. Prepr. 1989, 30, 157.
3. A number of polyacetylene graft copolymers have been made. See: (a) Armes, S. P.; Vincent, B.; White, J. W. J. Chem. Soc., Chem. Commun. 1986, 1525. (b) Dorsinville, R.; Tubino, R.; Krimchansky, S.; Alfano, R. R.; Birman, J. L.; Bolognesi, A.; Destri, S.; Catellani, M.; Porzio, W. Phys. Rev. B 1985, 32, 3377. (c) Tubino, R.; Dorsinville, R.; Lam, W.; Alfano, R. R.; Birman, J. L.; Bolognesi, A.; Destri, S.; Catellani, M.; Porzio, W. Phys. Rev. B 1984, 30, 6601. (d) Baker, G. L.; Bates, F. S. Macromolecules 1984, 17, 2619. (e) Stowell, J. A.; Amass, A. J.; Beevers, M. S.; Farren, T. R. Makromol. Chem. 1987, 188, 1635.
4. Nonconjugated polyacetylenes have been prepared: (a) Zeigler, J. M. U. S. Patent Appl. US 760 433 AO, November 21, 1986; Chem. Abstr. 1986, 20, 157042. (b) Zeigler, J. M. Polym. Prep. 1984, 25, 223. (c) Okano, Y.; Masuda, T.; Higashimura, T. J. Polym. Sci.: Polym. Chem. Ed. 1984, 22, 1603. (d) Masuda, T.; Higashimura, T. Adv. Polymer Science 1987, 81, 121.
5. (a) Grubbs, R. H. In Comprehensive Organometallic Chemistry; Wilkinson, G., Stone, F. G. A., Abel, E. W., Eds.; Pergamon: Oxford, 1982; Chapter 54. (b) Ivin, K. J. Olefin Metathesis; Academic: London, 1983. (c) Novak, B. M.; Grubbs, R. H. In Encyclopedia of Polymer Science and Engineering-, Kroschwitz, J. I., Ed.; John Wiley & Sons: New York, 1989, in press.
6. Lewis acidic metathesis catalysts have been used to polymerize cyclooctatetraene, resulting in a polymer containing many sp3defects: (a) Tlenkopachev, M. A.; Korshak, Y. V.; Orlov, A. V.; Korshak, V. V. Dokl. Akad. Nauk SSSR (Engl. Transl.) 1986, 291, 1036; Dokl. Akad. Nauk SSSR 1986, 291, 409. (b) Korshak, Y. V.; Korshak, V.; Kansichka, G.; Hocker, H. Makromol. Chem. Rapid Commun. 1985, 6, 685.
7. Klavetter, F. L.; Grubbs, R. H. J. Am. Chem. Soc. 1988, 110, 7807.
8. Gorman, C. B.; Ginsburg, E. J.; Marder, S. R.; Perry, J. W.; Grubbs, R. H., submitted.
9. 2was used. (a) For R = t-Bu, Ar = 2, 6-diisopropylphenyl, see: Schrock, R. R.; DePue, R. T.; Feldman, J.; Schaverien, C. J.; Dewan, J. C.; Liu, A. H. J. Am. Chem. Soc. 1988, 110, 1423. (b) Johnson, L. K.; Virgil, S. C.; Grubbs, R. H., manuscript in preparation.
10. Cooke, M.; Russ, C. R.; Stone, F. G. A. J. Chem. Soc., Dalton Trans. 1975, 256.
11. For a discussion of cis-trans photoisomerization, see: Turro, N. J. Modern Molecular Photochemistry; Benjamin/Cummings: Menlo Park, CA, 1978; Chapter 12.
12. Chien, J. C. W. Polyacetylene: Chemistry, Physics, and Material Science; Academic: Orlando, FL, 1984.
13. Sze, S. M. Physics of Semiconductor Devices; John Wiley & Sons: New York, 1981; p 30.
14. Schrock, R. R.; Krouse, S. A.; Knoll, K.; Feldman, J.; Murdzek, J. S.; Yang, D. C. J. Mol. Catal. 1988, 46, 243.
15. Petit, M. A.; Soum, A. H.; Leclerc, M.; Prud'homme, R. E. J. Polym. Sci.: Part B: Polym. Phys. 1987, 25, 423.
16. For discussions of third-order nonlinear optical properties in organic materials, see: Nonlinear Optical Properties of Organic Molecules and Crystals, Vol. 2; Chemla, D. S., Zyss, J., Eds.; Academic: Orlando, FL, 1987.
17. Sailor, M. J.; Lewis, N. S.; Ginsburg, E. J.; Gorman, C. B.; Marder, S. R.; Grubbs, R. H., manuscript in preparation.