Palladium-mediated soluble precursor route into poly(arylethynylenes) and poly(arylethylenes)

Macromolecules

Volumn 30, Issue 20, 1997, Pages 6047-6055

  Goodson, Felix E ^a,b   Novak, Bruce M ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b YALE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CHEMICAL BONDS; CONDENSATION; DECOMPOSITION; GAS CHROMATOGRAPHY; MASS SPECTROMETRY; PALLADIUM; PHASE TRANSITIONS; SYNTHESIS (CHEMICAL); THERMOANALYSIS; THERMOGRAVIMETRIC ANALYSIS;

CONCOMITANT DECOMPOSITION; POLYARYLETHYLENES; POLYARYLETHYNYLENES; RETRO-DIELS-ALDER REACTION; SOLUBLE PRECURSOR POLYMER;

AROMATIC POLYMERS;

EID: 0031556517     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma970323o     Document Type: Article

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19. For reviews see (c) Wegner, G. Angew. Chem., Int. Ed. Engl. 1981, 20, 361. (d) Baughman, R. H.; Brédas, J. L.; Chance, R. R.; Elsenbaumer, R. L.; Shacklette, L. W. Chem. Rev. 1982, 82, 209. (e) Yamamoto, T. Prog. Polym. Sci. 1992, 17, 1153. For recent examples, see (f) Smitzis, D.; Tzevelekis, A.; Stamboulis, A.; Hinrichsen, G. Acta Polym. 1993, 44, 294. (g) Meerholz, K.; Heinze, J. Synth. Met. 1993, 57, 5040. (h) Chaturvedi, V.; Tanaka, S.; Kaeriyama, K. Macromolecules 1993, 26, 2607. (i) Shi, G.; Xue, G.; Li, C.; Jin, S.; Yu, B. Macromolecules 1994, 27, 3679. (j) Kobayshi, K.; Yang, T. X.; Maruyama, K.; Shimomura, M.; Miyauchi, S. Synth. Met. 1995, 69, 475. (k) Kaeriyama, K.; Mehta, M. A.; Masuda, H. Synth. Met. 1995, 69, 507. (l) Moon, K.-J.; Lee, K.-S.; Shim, H.-K. Synth. Met. 1995, 71, 1719. (m) Ofer, D.; Swager, T. M.; Wrighton, M. S. Chem. Mater. 1995, 7, 418.
20. For reviews see (c) Wegner, G. Angew. Chem., Int. Ed. Engl. 1981, 20, 361. (d) Baughman, R. H.; Brédas, J. L.; Chance, R. R.; Elsenbaumer, R. L.; Shacklette, L. W. Chem. Rev. 1982, 82, 209. (e) Yamamoto, T. Prog. Polym. Sci. 1992, 17, 1153. For recent examples, see (f) Smitzis, D.; Tzevelekis, A.; Stamboulis, A.; Hinrichsen, G. Acta Polym. 1993, 44, 294. (g) Meerholz, K.; Heinze, J. Synth. Met. 1993, 57, 5040. (h) Chaturvedi, V.; Tanaka, S.; Kaeriyama, K. Macromolecules 1993, 26, 2607. (i) Shi, G.; Xue, G.; Li, C.; Jin, S.; Yu, B. Macromolecules 1994, 27, 3679. (j) Kobayshi, K.; Yang, T. X.; Maruyama, K.; Shimomura, M.; Miyauchi, S. Synth. Met. 1995, 69, 475. (k) Kaeriyama, K.; Mehta, M. A.; Masuda, H. Synth. Met. 1995, 69, 507. (l) Moon, K.-J.; Lee, K.-S.; Shim, H.-K. Synth. Met. 1995, 71, 1719. (m) Ofer, D.; Swager, T. M.; Wrighton, M. S. Chem. Mater. 1995, 7, 418.
21. For reviews see (c) Wegner, G. Angew. Chem., Int. Ed. Engl. 1981, 20, 361. (d) Baughman, R. H.; Brédas, J. L.; Chance, R. R.; Elsenbaumer, R. L.; Shacklette, L. W. Chem. Rev. 1982, 82, 209. (e) Yamamoto, T. Prog. Polym. Sci. 1992, 17, 1153. For recent examples, see (f) Smitzis, D.; Tzevelekis, A.; Stamboulis, A.; Hinrichsen, G. Acta Polym. 1993, 44, 294. (g) Meerholz, K.; Heinze, J. Synth. Met. 1993, 57, 5040. (h) Chaturvedi, V.; Tanaka, S.; Kaeriyama, K. Macromolecules 1993, 26, 2607. (i) Shi, G.; Xue, G.; Li, C.; Jin, S.; Yu, B. Macromolecules 1994, 27, 3679. (j) Kobayshi, K.; Yang, T. X.; Maruyama, K.; Shimomura, M.; Miyauchi, S. Synth. Met. 1995, 69, 475. (k) Kaeriyama, K.; Mehta, M. A.; Masuda, H. Synth. Met. 1995, 69, 507. (l) Moon, K.-J.; Lee, K.-S.; Shim, H.-K. Synth. Met. 1995, 71, 1719. (m) Ofer, D.; Swager, T. M.; Wrighton, M. S. Chem. Mater. 1995, 7, 418.
22. For reviews see (c) Wegner, G. Angew. Chem., Int. Ed. Engl. 1981, 20, 361. (d) Baughman, R. H.; Brédas, J. L.; Chance, R. R.; Elsenbaumer, R. L.; Shacklette, L. W. Chem. Rev. 1982, 82, 209. (e) Yamamoto, T. Prog. Polym. Sci. 1992, 17, 1153. For recent examples, see (f) Smitzis, D.; Tzevelekis, A.; Stamboulis, A.; Hinrichsen, G. Acta Polym. 1993, 44, 294. (g) Meerholz, K.; Heinze, J. Synth. Met. 1993, 57, 5040. (h) Chaturvedi, V.; Tanaka, S.; Kaeriyama, K. Macromolecules 1993, 26, 2607. (i) Shi, G.; Xue, G.; Li, C.; Jin, S.; Yu, B. Macromolecules 1994, 27, 3679. (j) Kobayshi, K.; Yang, T. X.; Maruyama, K.; Shimomura, M.; Miyauchi, S. Synth. Met. 1995, 69, 475. (k) Kaeriyama, K.; Mehta, M. A.; Masuda, H. Synth. Met. 1995, 69, 507. (l) Moon, K.-J.; Lee, K.-S.; Shim, H.-K. Synth. Met. 1995, 71, 1719. (m) Ofer, D.; Swager, T. M.; Wrighton, M. S. Chem. Mater. 1995, 7, 418.
23. For reviews see (c) Wegner, G. Angew. Chem., Int. Ed. Engl. 1981, 20, 361. (d) Baughman, R. H.; Brédas, J. L.; Chance, R. R.; Elsenbaumer, R. L.; Shacklette, L. W. Chem. Rev. 1982, 82, 209. (e) Yamamoto, T. Prog. Polym. Sci. 1992, 17, 1153. For recent examples, see (f) Smitzis, D.; Tzevelekis, A.; Stamboulis, A.; Hinrichsen, G. Acta Polym. 1993, 44, 294. (g) Meerholz, K.; Heinze, J. Synth. Met. 1993, 57, 5040. (h) Chaturvedi, V.; Tanaka, S.; Kaeriyama, K. Macromolecules 1993, 26, 2607. (i) Shi, G.; Xue, G.; Li, C.; Jin, S.; Yu, B. Macromolecules 1994, 27, 3679. (j) Kobayshi, K.; Yang, T. X.; Maruyama, K.; Shimomura, M.; Miyauchi, S. Synth. Met. 1995, 69, 475. (k) Kaeriyama, K.; Mehta, M. A.; Masuda, H. Synth. Met. 1995, 69, 507. (l) Moon, K.-J.; Lee, K.-S.; Shim, H.-K. Synth. Met. 1995, 71, 1719. (m) Ofer, D.; Swager, T. M.; Wrighton, M. S. Chem. Mater. 1995, 7, 418.
24. For reviews see (c) Wegner, G. Angew. Chem., Int. Ed. Engl. 1981, 20, 361. (d) Baughman, R. H.; Brédas, J. L.; Chance, R. R.; Elsenbaumer, R. L.; Shacklette, L. W. Chem. Rev. 1982, 82, 209. (e) Yamamoto, T. Prog. Polym. Sci. 1992, 17, 1153. For recent examples, see (f) Smitzis, D.; Tzevelekis, A.; Stamboulis, A.; Hinrichsen, G. Acta Polym. 1993, 44, 294. (g) Meerholz, K.; Heinze, J. Synth. Met. 1993, 57, 5040. (h) Chaturvedi, V.; Tanaka, S.; Kaeriyama, K. Macromolecules 1993, 26, 2607. (i) Shi, G.; Xue, G.; Li, C.; Jin, S.; Yu, B. Macromolecules 1994, 27, 3679. (j) Kobayshi, K.; Yang, T. X.; Maruyama, K.; Shimomura, M.; Miyauchi, S. Synth. Met. 1995, 69, 475. (k) Kaeriyama, K.; Mehta, M. A.; Masuda, H. Synth. Met. 1995, 69, 507. (l) Moon, K.-J.; Lee, K.-S.; Shim, H.-K. Synth. Met. 1995, 71, 1719. (m) Ofer, D.; Swager, T. M.; Wrighton, M. S. Chem. Mater. 1995, 7, 418.
25. For reviews see (c) Wegner, G. Angew. Chem., Int. Ed. Engl. 1981, 20, 361. (d) Baughman, R. H.; Brédas, J. L.; Chance, R. R.; Elsenbaumer, R. L.; Shacklette, L. W. Chem. Rev. 1982, 82, 209. (e) Yamamoto, T. Prog. Polym. Sci. 1992, 17, 1153. For recent examples, see (f) Smitzis, D.; Tzevelekis, A.; Stamboulis, A.; Hinrichsen, G. Acta Polym. 1993, 44, 294. (g) Meerholz, K.; Heinze, J. Synth. Met. 1993, 57, 5040. (h) Chaturvedi, V.; Tanaka, S.; Kaeriyama, K. Macromolecules 1993, 26, 2607. (i) Shi, G.; Xue, G.; Li, C.; Jin, S.; Yu, B. Macromolecules 1994, 27, 3679. (j) Kobayshi, K.; Yang, T. X.; Maruyama, K.; Shimomura, M.; Miyauchi, S. Synth. Met. 1995, 69, 475. (k) Kaeriyama, K.; Mehta, M. A.; Masuda, H. Synth. Met. 1995, 69, 507. (l) Moon, K.-J.; Lee, K.-S.; Shim, H.-K. Synth. Met. 1995, 71, 1719. (m) Ofer, D.; Swager, T. M.; Wrighton, M. S. Chem. Mater. 1995, 7, 418.
26. For reviews see (c) Wegner, G. Angew. Chem., Int. Ed. Engl. 1981, 20, 361. (d) Baughman, R. H.; Brédas, J. L.; Chance, R. R.; Elsenbaumer, R. L.; Shacklette, L. W. Chem. Rev. 1982, 82, 209. (e) Yamamoto, T. Prog. Polym. Sci. 1992, 17, 1153. For recent examples, see (f) Smitzis, D.; Tzevelekis, A.; Stamboulis, A.; Hinrichsen, G. Acta Polym. 1993, 44, 294. (g) Meerholz, K.; Heinze, J. Synth. Met. 1993, 57, 5040. (h) Chaturvedi, V.; Tanaka, S.; Kaeriyama, K. Macromolecules 1993, 26, 2607. (i) Shi, G.; Xue, G.; Li, C.; Jin, S.; Yu, B. Macromolecules 1994, 27, 3679. (j) Kobayshi, K.; Yang, T. X.; Maruyama, K.; Shimomura, M.; Miyauchi, S. Synth. Met. 1995, 69, 475. (k) Kaeriyama, K.; Mehta, M. A.; Masuda, H. Synth. Met. 1995, 69, 507. (l) Moon, K.-J.; Lee, K.-S.; Shim, H.-K. Synth. Met. 1995, 71, 1719. (m) Ofer, D.; Swager, T. M.; Wrighton, M. S. Chem. Mater. 1995, 7, 418.
27. For reviews see (c) Wegner, G. Angew. Chem., Int. Ed. Engl. 1981, 20, 361. (d) Baughman, R. H.; Brédas, J. L.; Chance, R. R.; Elsenbaumer, R. L.; Shacklette, L. W. Chem. Rev. 1982, 82, 209. (e) Yamamoto, T. Prog. Polym. Sci. 1992, 17, 1153. For recent examples, see (f) Smitzis, D.; Tzevelekis, A.; Stamboulis, A.; Hinrichsen, G. Acta Polym. 1993, 44, 294. (g) Meerholz, K.; Heinze, J. Synth. Met. 1993, 57, 5040. (h) Chaturvedi, V.; Tanaka, S.; Kaeriyama, K. Macromolecules 1993, 26, 2607. (i) Shi, G.; Xue, G.; Li, C.; Jin, S.; Yu, B. Macromolecules 1994, 27, 3679. (j) Kobayshi, K.; Yang, T. X.; Maruyama, K.; Shimomura, M.; Miyauchi, S. Synth. Met. 1995, 69, 475. (k) Kaeriyama, K.; Mehta, M. A.; Masuda, H. Synth. Met. 1995, 69, 507. (l) Moon, K.-J.; Lee, K.-S.; Shim, H.-K. Synth. Met. 1995, 71, 1719. (m) Ofer, D.; Swager, T. M.; Wrighton, M. S. Chem. Mater. 1995, 7, 418.
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44. For early examples, see: (a) Edwards, G. A.; Goldfinger, G. J. Polym. Sci. 1955, 16, 589. (b) Kern, W.; Gehm. R.; Seibel, M. Makromol Chem. 1955, 15, 170. (c) McDonald, R. N.; Campbell, T. W. J. Am. Chem. Soc. 1960, 82, 4669. (d) Berlin, A. A.; Liogon'kii, V. I.; Parini, V. P. J. Polym. Sci. 1963, 55, 675. (e) Kovacic, P.; Kyriakis, A. J. Am. Chem. Soc. 1961, 85, 454. (f) Kovacic, P.; Oziomek, J. J. Org. Chem. 1963,29, 100. For a review, see (g) Kovacic, P.; Jones, M. B. Chem. Rev. 1987, 87, 357.
45. For early examples, see: (a) Edwards, G. A.; Goldfinger, G. J. Polym. Sci. 1955, 16, 589. (b) Kern, W.; Gehm. R.; Seibel, M. Makromol Chem. 1955, 15, 170. (c) McDonald, R. N.; Campbell, T. W. J. Am. Chem. Soc. 1960, 82, 4669. (d) Berlin, A. A.; Liogon'kii, V. I.; Parini, V. P. J. Polym. Sci. 1963, 55, 675. (e) Kovacic, P.; Kyriakis, A. J. Am. Chem. Soc. 1961, 85, 454. (f) Kovacic, P.; Oziomek, J. J. Org. Chem. 1963,29, 100. For a review, see (g) Kovacic, P.; Jones, M. B. Chem. Rev. 1987, 87, 357.
46. For early examples, see: (a) Edwards, G. A.; Goldfinger, G. J. Polym. Sci. 1955, 16, 589. (b) Kern, W.; Gehm. R.; Seibel, M. Makromol Chem. 1955, 15, 170. (c) McDonald, R. N.; Campbell, T. W. J. Am. Chem. Soc. 1960, 82, 4669. (d) Berlin, A. A.; Liogon'kii, V. I.; Parini, V. P. J. Polym. Sci. 1963, 55, 675. (e) Kovacic, P.; Kyriakis, A. J. Am. Chem. Soc. 1961, 85, 454. (f) Kovacic, P.; Oziomek, J. J. Org. Chem. 1963,29, 100. For a review, see (g) Kovacic, P.; Jones, M. B. Chem. Rev. 1987, 87, 357.
47. For early examples, see: (a) Edwards, G. A.; Goldfinger, G. J. Polym. Sci. 1955, 16, 589. (b) Kern, W.; Gehm. R.; Seibel, M. Makromol Chem. 1955, 15, 170. (c) McDonald, R. N.; Campbell, T. W. J. Am. Chem. Soc. 1960, 82, 4669. (d) Berlin, A. A.; Liogon'kii, V. I.; Parini, V. P. J. Polym. Sci. 1963, 55, 675. (e) Kovacic, P.; Kyriakis, A. J. Am. Chem. Soc. 1961, 85, 454. (f) Kovacic, P.; Oziomek, J. J. Org. Chem. 1963,29, 100. For a review, see (g) Kovacic, P.; Jones, M. B. Chem. Rev. 1987, 87, 357.
48. For early examples, see: (a) Edwards, G. A.; Goldfinger, G. J. Polym. Sci. 1955, 16, 589. (b) Kern, W.; Gehm. R.; Seibel, M. Makromol Chem. 1955, 15, 170. (c) McDonald, R. N.; Campbell, T. W. J. Am. Chem. Soc. 1960, 82, 4669. (d) Berlin, A. A.; Liogon'kii, V. I.; Parini, V. P. J. Polym. Sci. 1963, 55, 675. (e) Kovacic, P.; Kyriakis, A. J. Am. Chem. Soc. 1961, 85, 454. (f) Kovacic, P.; Oziomek, J. J. Org. Chem. 1963,29, 100. For a review, see (g) Kovacic, P.; Jones, M. B. Chem. Rev. 1987, 87, 357.
49. For early examples, see: (a) Edwards, G. A.; Goldfinger, G. J. Polym. Sci. 1955, 16, 589. (b) Kern, W.; Gehm. R.; Seibel, M. Makromol Chem. 1955, 15, 170. (c) McDonald, R. N.; Campbell, T. W. J. Am. Chem. Soc. 1960, 82, 4669. (d) Berlin, A. A.; Liogon'kii, V. I.; Parini, V. P. J. Polym. Sci. 1963, 55, 675. (e) Kovacic, P.; Kyriakis, A. J. Am. Chem. Soc. 1961, 85, 454. (f) Kovacic, P.; Oziomek, J. J. Org. Chem. 1963,29, 100. For a review, see (g) Kovacic, P.; Jones, M. B. Chem. Rev. 1987, 87, 357.
50. For reviews on soluble PPP and derivatives, see: (a) Reference 2e. (b) Schlüter, A.-D.; Wegner, G. Acta Polym. 1993, 44, 59. (c) Tour, J. M. Adv. Mater. 1994, 6, 190. (d) Percec, V.; Hill, D. H. ACS Symp. Ser. 1996, 624, 2. For recent examples, see (e) Percec, V.; Zhao, M.; Bae, J.-Y.; Hill, D. H. Macromolecules 1996, 29, 3727. (f) Vanhee, S.; Rulkens, R.; Lehmann, U.; Rosenauer, C.; Schulze, M.; Köhler, W.; Wegner, G. Macromolecules 1996, 29, 5136. For recent examples of soluble PPE and derivatives, see (g) Moroni, M.; Le Moigne, J.; Luzzati, S. Macromolecules 1994, 27, 562. (h) Yamamoto, T.; Yamada, W.; Takagi, M.; Kizu, K.; Maruyama, T.; Ooba, N.; Tomaru, S.; Kurihara, T.; Kaino, T.; Kubota, K. Macromolecules 1994, 27, 6620. (i) Reference 2m. (j) Reference 4j. (k) Weiss, K.; Michel, A.; Auth, E.-M.; Bunz, U. H. F.; Mangel, T.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 506.
51. For reviews on soluble PPP and derivatives, see: (a) Reference 2e. (b) Schlüter, A.-D.; Wegner, G. Acta Polym. 1993, 44, 59. (c) Tour, J. M. Adv. Mater. 1994, 6, 190. (d) Percec, V.; Hill, D. H. ACS Symp. Ser. 1996, 624, 2. For recent examples, see (e) Percec, V.; Zhao, M.; Bae, J.-Y.; Hill, D. H. Macromolecules 1996, 29, 3727. (f) Vanhee, S.; Rulkens, R.; Lehmann, U.; Rosenauer, C.; Schulze, M.; Köhler, W.; Wegner, G. Macromolecules 1996, 29, 5136. For recent examples of soluble PPE and derivatives, see (g) Moroni, M.; Le Moigne, J.; Luzzati, S. Macromolecules 1994, 27, 562. (h) Yamamoto, T.; Yamada, W.; Takagi, M.; Kizu, K.; Maruyama, T.; Ooba, N.; Tomaru, S.; Kurihara, T.; Kaino, T.; Kubota, K. Macromolecules 1994, 27, 6620. (i) Reference 2m. (j) Reference 4j. (k) Weiss, K.; Michel, A.; Auth, E.-M.; Bunz, U. H. F.; Mangel, T.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 506.
52. For reviews on soluble PPP and derivatives, see: (a) Reference 2e. (b) Schlüter, A.-D.; Wegner, G. Acta Polym. 1993, 44, 59. (c) Tour, J. M. Adv. Mater. 1994, 6, 190. (d) Percec, V.; Hill, D. H. ACS Symp. Ser. 1996, 624, 2. For recent examples, see (e) Percec, V.; Zhao, M.; Bae, J.-Y.; Hill, D. H. Macromolecules 1996, 29, 3727. (f) Vanhee, S.; Rulkens, R.; Lehmann, U.; Rosenauer, C.; Schulze, M.; Köhler, W.; Wegner, G. Macromolecules 1996, 29, 5136. For recent examples of soluble PPE and derivatives, see (g) Moroni, M.; Le Moigne, J.; Luzzati, S. Macromolecules 1994, 27, 562. (h) Yamamoto, T.; Yamada, W.; Takagi, M.; Kizu, K.; Maruyama, T.; Ooba, N.; Tomaru, S.; Kurihara, T.; Kaino, T.; Kubota, K. Macromolecules 1994, 27, 6620. (i) Reference 2m. (j) Reference 4j. (k) Weiss, K.; Michel, A.; Auth, E.-M.; Bunz, U. H. F.; Mangel, T.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 506.
53. For reviews on soluble PPP and derivatives, see: (a) Reference 2e. (b) Schlüter, A.-D.; Wegner, G. Acta Polym. 1993, 44, 59. (c) Tour, J. M. Adv. Mater. 1994, 6, 190. (d) Percec, V.; Hill, D. H. ACS Symp. Ser. 1996, 624, 2. For recent examples, see (e) Percec, V.; Zhao, M.; Bae, J.-Y.; Hill, D. H. Macromolecules 1996, 29, 3727. (f) Vanhee, S.; Rulkens, R.; Lehmann, U.; Rosenauer, C.; Schulze, M.; Köhler, W.; Wegner, G. Macromolecules 1996, 29, 5136. For recent examples of soluble PPE and derivatives, see (g) Moroni, M.; Le Moigne, J.; Luzzati, S. Macromolecules 1994, 27, 562. (h) Yamamoto, T.; Yamada, W.; Takagi, M.; Kizu, K.; Maruyama, T.; Ooba, N.; Tomaru, S.; Kurihara, T.; Kaino, T.; Kubota, K. Macromolecules 1994, 27, 6620. (i) Reference 2m. (j) Reference 4j. (k) Weiss, K.; Michel, A.; Auth, E.-M.; Bunz, U. H. F.; Mangel, T.; Müllen, K. Angew. Chem., Int. Ed. Engl. 1997, 36, 506.
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