Application of "transfer-free" suzuki coupling protocols toward the synthesis of "unambiguously linear" poly(p-phenylenes)

Macromolecules

Volumn 31, Issue 7, 1998, Pages 2047-2056

  Goodson, Felix E ^a,b   Wallow, Thomas I ^a,c   Novak, Bruce M ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b YALE UNIVERSITY   (United States)

^c IBM ALMADEN RESEARCH CENTER   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

CATALYSIS; CATALYSTS; DERIVATIVES; GEL PERMEATION CHROMATOGRAPHY; LIGHT SCATTERING; MOLECULAR WEIGHT; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PALLADIUM; SOLVENTS; SYNTHESIS (CHEMICAL); VISCOSITY MEASUREMENT;

POLYPHENYLENE; TRANSFER FREE SUZUKI COUPLING PROTOCOL;

ORGANIC POLYMERS;

EID: 0032492532     PISSN: 00249297     EISSN: None     Source Type: Journal    
DOI: 10.1021/ma9717294     Document Type: Article

References (198)

1. For reviews on PPP and derivatives, see: (a) Kovacic, P.; Jones, M. B. Chem. Rev. 1987, 87, 357. (b) Yamamoto, T. Prog. Polym. Sci. 1992, 17, 1153. (c) Schlüter, A.-D.; Wegner, G. Acta Polym. 1993, 44, 59. (d) Tour, J. M. Adv. Mater. 1994, 6, 190. (e) Percec, V.; Hill, D. H. ACS Symp. Ser. 1996, 624, 2. For recent examples, see: (f) Percec, V.; Zhao, M.; Bae, J.-Y.; Hill, D. H. Macromolecules 1996, 29, 3727. (g) Vanhee, S.; Rulkens, R.; Lehmann, U.; Rosenauer, C.; Schulze, M.; Köhler, W.; Wegner, G. Macromolecules 1996, 29, 5136. (h) Grob, M. C.; Feiring, A. E.; Auman, B. C.; Percec, V.; Zhao, M.; Hill, D. H. Macromolecules 1996, 29, 7284.
2. For reviews on PPP and derivatives, see: (a) Kovacic, P.; Jones, M. B. Chem. Rev. 1987, 87, 357. (b) Yamamoto, T. Prog. Polym. Sci. 1992, 17, 1153. (c) Schlüter, A.-D.; Wegner, G. Acta Polym. 1993, 44, 59. (d) Tour, J. M. Adv. Mater. 1994, 6, 190. (e) Percec, V.; Hill, D. H. ACS Symp. Ser. 1996, 624, 2. For recent examples, see: (f) Percec, V.; Zhao, M.; Bae, J.-Y.; Hill, D. H. Macromolecules 1996, 29, 3727. (g) Vanhee, S.; Rulkens, R.; Lehmann, U.; Rosenauer, C.; Schulze, M.; Köhler, W.; Wegner, G. Macromolecules 1996, 29, 5136. (h) Grob, M. C.; Feiring, A. E.; Auman, B. C.; Percec, V.; Zhao, M.; Hill, D. H. Macromolecules 1996, 29, 7284.
3. For reviews on PPP and derivatives, see: (a) Kovacic, P.; Jones, M. B. Chem. Rev. 1987, 87, 357. (b) Yamamoto, T. Prog. Polym. Sci. 1992, 17, 1153. (c) Schlüter, A.-D.; Wegner, G. Acta Polym. 1993, 44, 59. (d) Tour, J. M. Adv. Mater. 1994, 6, 190. (e) Percec, V.; Hill, D. H. ACS Symp. Ser. 1996, 624, 2. For recent examples, see: (f) Percec, V.; Zhao, M.; Bae, J.-Y.; Hill, D. H. Macromolecules 1996, 29, 3727. (g) Vanhee, S.; Rulkens, R.; Lehmann, U.; Rosenauer, C.; Schulze, M.; Köhler, W.; Wegner, G. Macromolecules 1996, 29, 5136. (h) Grob, M. C.; Feiring, A. E.; Auman, B. C.; Percec, V.; Zhao, M.; Hill, D. H. Macromolecules 1996, 29, 7284.
4. For reviews on PPP and derivatives, see: (a) Kovacic, P.; Jones, M. B. Chem. Rev. 1987, 87, 357. (b) Yamamoto, T. Prog. Polym. Sci. 1992, 17, 1153. (c) Schlüter, A.-D.; Wegner, G. Acta Polym. 1993, 44, 59. (d) Tour, J. M. Adv. Mater. 1994, 6, 190. (e) Percec, V.; Hill, D. H. ACS Symp. Ser. 1996, 624, 2. For recent examples, see: (f) Percec, V.; Zhao, M.; Bae, J.-Y.; Hill, D. H. Macromolecules 1996, 29, 3727. (g) Vanhee, S.; Rulkens, R.; Lehmann, U.; Rosenauer, C.; Schulze, M.; Köhler, W.; Wegner, G. Macromolecules 1996, 29, 5136. (h) Grob, M. C.; Feiring, A. E.; Auman, B. C.; Percec, V.; Zhao, M.; Hill, D. H. Macromolecules 1996, 29, 7284.
5. For reviews on PPP and derivatives, see: (a) Kovacic, P.; Jones, M. B. Chem. Rev. 1987, 87, 357. (b) Yamamoto, T. Prog. Polym. Sci. 1992, 17, 1153. (c) Schlüter, A.-D.; Wegner, G. Acta Polym. 1993, 44, 59. (d) Tour, J. M. Adv. Mater. 1994, 6, 190. (e) Percec, V.; Hill, D. H. ACS Symp. Ser. 1996, 624, 2. For recent examples, see: (f) Percec, V.; Zhao, M.; Bae, J.-Y.; Hill, D. H. Macromolecules 1996, 29, 3727. (g) Vanhee, S.; Rulkens, R.; Lehmann, U.; Rosenauer, C.; Schulze, M.; Köhler, W.; Wegner, G. Macromolecules 1996, 29, 5136. (h) Grob, M. C.; Feiring, A. E.; Auman, B. C.; Percec, V.; Zhao, M.; Hill, D. H. Macromolecules 1996, 29, 7284.
6. For reviews on PPP and derivatives, see: (a) Kovacic, P.; Jones, M. B. Chem. Rev. 1987, 87, 357. (b) Yamamoto, T. Prog. Polym. Sci. 1992, 17, 1153. (c) Schlüter, A.-D.; Wegner, G. Acta Polym. 1993, 44, 59. (d) Tour, J. M. Adv. Mater. 1994, 6, 190. (e) Percec, V.; Hill, D. H. ACS Symp. Ser. 1996, 624, 2. For recent examples, see: (f) Percec, V.; Zhao, M.; Bae, J.-Y.; Hill, D. H. Macromolecules 1996, 29, 3727. (g) Vanhee, S.; Rulkens, R.; Lehmann, U.; Rosenauer, C.; Schulze, M.; Köhler, W.; Wegner, G. Macromolecules 1996, 29, 5136. (h) Grob, M. C.; Feiring, A. E.; Auman, B. C.; Percec, V.; Zhao, M.; Hill, D. H. Macromolecules 1996, 29, 7284.
7. For reviews on PPP and derivatives, see: (a) Kovacic, P.; Jones, M. B. Chem. Rev. 1987, 87, 357. (b) Yamamoto, T. Prog. Polym. Sci. 1992, 17, 1153. (c) Schlüter, A.-D.; Wegner, G. Acta Polym. 1993, 44, 59. (d) Tour, J. M. Adv. Mater. 1994, 6, 190. (e) Percec, V.; Hill, D. H. ACS Symp. Ser. 1996, 624, 2. For recent examples, see: (f) Percec, V.; Zhao, M.; Bae, J.-Y.; Hill, D. H. Macromolecules 1996, 29, 3727. (g) Vanhee, S.; Rulkens, R.; Lehmann, U.; Rosenauer, C.; Schulze, M.; Köhler, W.; Wegner, G. Macromolecules 1996, 29, 5136. (h) Grob, M. C.; Feiring, A. E.; Auman, B. C.; Percec, V.; Zhao, M.; Hill, D. H. Macromolecules 1996, 29, 7284.
8. For reviews on PPP and derivatives, see: (a) Kovacic, P.; Jones, M. B. Chem. Rev. 1987, 87, 357. (b) Yamamoto, T. Prog. Polym. Sci. 1992, 17, 1153. (c) Schlüter, A.-D.; Wegner, G. Acta Polym. 1993, 44, 59. (d) Tour, J. M. Adv. Mater. 1994, 6, 190. (e) Percec, V.; Hill, D. H. ACS Symp. Ser. 1996, 624, 2. For recent examples, see: (f) Percec, V.; Zhao, M.; Bae, J.-Y.; Hill, D. H. Macromolecules 1996, 29, 3727. (g) Vanhee, S.; Rulkens, R.; Lehmann, U.; Rosenauer, C.; Schulze, M.; Köhler, W.; Wegner, G. Macromolecules 1996, 29, 5136. (h) Grob, M. C.; Feiring, A. E.; Auman, B. C.; Percec, V.; Zhao, M.; Hill, D. H. Macromolecules 1996, 29, 7284.
9. For examples of PPV and derivatives, see: (a) McDonald, R. N.; Campbell, T. W. J. Am. Chem. Soc. 1960, 82, 4669. (b) Wessling, R. A.; Zimmerman, R. G. U.S. Patents 3, 401, 152, 1968; 3, 404,132, 1968; 3, 532,643, 1970; 3, 706,677, 1972. (c) Wessling, R. A. J. Polym. Sci., Polym. Symp. 1985, 72, 55. (d) Gagnon, D. R.; Capistran, J. D.; Karasz, F. E.; Lenz, R. W.; Antoun, S. Polymer 1987, 28, 567. (e) Heitz, W.; Brügging, W.; Freund, L.; Gailberger, M.; Greiner, A.; Jung, G.; Kampschulte, U.; Niessner, N.; Osan, F.; Schmidt, H.-W.; Wicker, M. Makromol. Chem. 1988, 189, 119. (f) Lenz, R. W.; Han, C.-C.; Stenger-Smith, J.; Karasz, F. E. J. Polym. Sci., Polym. Chem. Ed. 1988, 26, 3241. (g) Momii, T.; Tokito, S.; Tsutsui, T.; Saito, S. Chem. Lett. 1988, 1201. (h) Tokito, S.; Smith, P.; Heeger, A. J. Polymer 1991, 32, 464. (i) Burn, P. L.; Bradley, D. D. C.; Friend, R. H.; Halliday, D. A.; Holmes, A. B.; Jackson, R. W.; Kraft, A. J. Chem. Soc., Perkin Trans, 1 1992, 3225. (j) Conticello, V. P.; Gin, D. L.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 9708. (k) Hilberer, A.; Brouwer, H.-J.; van der Scheer, B.-J.; Wildeman, J.; Hadziioannou, G. Macromolecules 1995, 28, 4525.
10. For examples of PPV and derivatives, see: (a) McDonald, R. N.; Campbell, T. W. J. Am. Chem. Soc. 1960, 82, 4669. (b) Wessling, R. A.; Zimmerman, R. G. U.S. Patents 3, 401, 152, 1968; 3, 404,132, 1968; 3, 532,643, 1970; 3, 706,677, 1972. (c) Wessling, R. A. J. Polym. Sci., Polym. Symp. 1985, 72, 55. (d) Gagnon, D. R.; Capistran, J. D.; Karasz, F. E.; Lenz, R. W.; Antoun, S. Polymer 1987, 28, 567. (e) Heitz, W.; Brügging, W.; Freund, L.; Gailberger, M.; Greiner, A.; Jung, G.; Kampschulte, U.; Niessner, N.; Osan, F.; Schmidt, H.-W.; Wicker, M. Makromol. Chem. 1988, 189, 119. (f) Lenz, R. W.; Han, C.-C.; Stenger-Smith, J.; Karasz, F. E. J. Polym. Sci., Polym. Chem. Ed. 1988, 26, 3241. (g) Momii, T.; Tokito, S.; Tsutsui, T.; Saito, S. Chem. Lett. 1988, 1201. (h) Tokito, S.; Smith, P.; Heeger, A. J. Polymer 1991, 32, 464. (i) Burn, P. L.; Bradley, D. D. C.; Friend, R. H.; Halliday, D. A.; Holmes, A. B.; Jackson, R. W.; Kraft, A. J. Chem. Soc., Perkin Trans, 1 1992, 3225. (j) Conticello, V. P.; Gin, D. L.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 9708. (k) Hilberer, A.; Brouwer, H.-J.; van der Scheer, B.-J.; Wildeman, J.; Hadziioannou, G. Macromolecules 1995, 28, 4525.
11. For examples of PPV and derivatives, see: (a) McDonald, R. N.; Campbell, T. W. J. Am. Chem. Soc. 1960, 82, 4669. (b) Wessling, R. A.; Zimmerman, R. G. U.S. Patents 3, 401, 152, 1968; 3, 404,132, 1968; 3, 532,643, 1970; 3, 706,677, 1972. (c) Wessling, R. A. J. Polym. Sci., Polym. Symp. 1985, 72, 55. (d) Gagnon, D. R.; Capistran, J. D.; Karasz, F. E.; Lenz, R. W.; Antoun, S. Polymer 1987, 28, 567. (e) Heitz, W.; Brügging, W.; Freund, L.; Gailberger, M.; Greiner, A.; Jung, G.; Kampschulte, U.; Niessner, N.; Osan, F.; Schmidt, H.-W.; Wicker, M. Makromol. Chem. 1988, 189, 119. (f) Lenz, R. W.; Han, C.-C.; Stenger-Smith, J.; Karasz, F. E. J. Polym. Sci., Polym. Chem. Ed. 1988, 26, 3241. (g) Momii, T.; Tokito, S.; Tsutsui, T.; Saito, S. Chem. Lett. 1988, 1201. (h) Tokito, S.; Smith, P.; Heeger, A. J. Polymer 1991, 32, 464. (i) Burn, P. L.; Bradley, D. D. C.; Friend, R. H.; Halliday, D. A.; Holmes, A. B.; Jackson, R. W.; Kraft, A. J. Chem. Soc., Perkin Trans, 1 1992, 3225. (j) Conticello, V. P.; Gin, D. L.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 9708. (k) Hilberer, A.; Brouwer, H.-J.; van der Scheer, B.-J.; Wildeman, J.; Hadziioannou, G. Macromolecules 1995, 28, 4525.
12. For examples of PPV and derivatives, see: (a) McDonald, R. N.; Campbell, T. W. J. Am. Chem. Soc. 1960, 82, 4669. (b) Wessling, R. A.; Zimmerman, R. G. U.S. Patents 3, 401, 152, 1968; 3, 404,132, 1968; 3, 532,643, 1970; 3, 706,677, 1972. (c) Wessling, R. A. J. Polym. Sci., Polym. Symp. 1985, 72, 55. (d) Gagnon, D. R.; Capistran, J. D.; Karasz, F. E.; Lenz, R. W.; Antoun, S. Polymer 1987, 28, 567. (e) Heitz, W.; Brügging, W.; Freund, L.; Gailberger, M.; Greiner, A.; Jung, G.; Kampschulte, U.; Niessner, N.; Osan, F.; Schmidt, H.-W.; Wicker, M. Makromol. Chem. 1988, 189, 119. (f) Lenz, R. W.; Han, C.-C.; Stenger-Smith, J.; Karasz, F. E. J. Polym. Sci., Polym. Chem. Ed. 1988, 26, 3241. (g) Momii, T.; Tokito, S.; Tsutsui, T.; Saito, S. Chem. Lett. 1988, 1201. (h) Tokito, S.; Smith, P.; Heeger, A. J. Polymer 1991, 32, 464. (i) Burn, P. L.; Bradley, D. D. C.; Friend, R. H.; Halliday, D. A.; Holmes, A. B.; Jackson, R. W.; Kraft, A. J. Chem. Soc., Perkin Trans, 1 1992, 3225. (j) Conticello, V. P.; Gin, D. L.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 9708. (k) Hilberer, A.; Brouwer, H.-J.; van der Scheer, B.-J.; Wildeman, J.; Hadziioannou, G. Macromolecules 1995, 28, 4525.
13. For examples of PPV and derivatives, see: (a) McDonald, R. N.; Campbell, T. W. J. Am. Chem. Soc. 1960, 82, 4669. (b) Wessling, R. A.; Zimmerman, R. G. U.S. Patents 3, 401, 152, 1968; 3, 404,132, 1968; 3, 532,643, 1970; 3, 706,677, 1972. (c) Wessling, R. A. J. Polym. Sci., Polym. Symp. 1985, 72, 55. (d) Gagnon, D. R.; Capistran, J. D.; Karasz, F. E.; Lenz, R. W.; Antoun, S. Polymer 1987, 28, 567. (e) Heitz, W.; Brügging, W.; Freund, L.; Gailberger, M.; Greiner, A.; Jung, G.; Kampschulte, U.; Niessner, N.; Osan, F.; Schmidt, H.-W.; Wicker, M. Makromol. Chem. 1988, 189, 119. (f) Lenz, R. W.; Han, C.-C.; Stenger-Smith, J.; Karasz, F. E. J. Polym. Sci., Polym. Chem. Ed. 1988, 26, 3241. (g) Momii, T.; Tokito, S.; Tsutsui, T.; Saito, S. Chem. Lett. 1988, 1201. (h) Tokito, S.; Smith, P.; Heeger, A. J. Polymer 1991, 32, 464. (i) Burn, P. L.; Bradley, D. D. C.; Friend, R. H.; Halliday, D. A.; Holmes, A. B.; Jackson, R. W.; Kraft, A. J. Chem. Soc., Perkin Trans, 1 1992, 3225. (j) Conticello, V. P.; Gin, D. L.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 9708. (k) Hilberer, A.; Brouwer, H.-J.; van der Scheer, B.-J.; Wildeman, J.; Hadziioannou, G. Macromolecules 1995, 28, 4525.
14. For examples of PPV and derivatives, see: (a) McDonald, R. N.; Campbell, T. W. J. Am. Chem. Soc. 1960, 82, 4669. (b) Wessling, R. A.; Zimmerman, R. G. U.S. Patents 3, 401, 152, 1968; 3, 404,132, 1968; 3, 532,643, 1970; 3, 706,677, 1972. (c) Wessling, R. A. J. Polym. Sci., Polym. Symp. 1985, 72, 55. (d) Gagnon, D. R.; Capistran, J. D.; Karasz, F. E.; Lenz, R. W.; Antoun, S. Polymer 1987, 28, 567. (e) Heitz, W.; Brügging, W.; Freund, L.; Gailberger, M.; Greiner, A.; Jung, G.; Kampschulte, U.; Niessner, N.; Osan, F.; Schmidt, H.-W.; Wicker, M. Makromol. Chem. 1988, 189, 119. (f) Lenz, R. W.; Han, C.-C.; Stenger-Smith, J.; Karasz, F. E. J. Polym. Sci., Polym. Chem. Ed. 1988, 26, 3241. (g) Momii, T.; Tokito, S.; Tsutsui, T.; Saito, S. Chem. Lett. 1988, 1201. (h) Tokito, S.; Smith, P.; Heeger, A. J. Polymer 1991, 32, 464. (i) Burn, P. L.; Bradley, D. D. C.; Friend, R. H.; Halliday, D. A.; Holmes, A. B.; Jackson, R. W.; Kraft, A. J. Chem. Soc., Perkin Trans, 1 1992, 3225. (j) Conticello, V. P.; Gin, D. L.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 9708. (k) Hilberer, A.; Brouwer, H.-J.; van der Scheer, B.-J.; Wildeman, J.; Hadziioannou, G. Macromolecules 1995, 28, 4525.
15. For examples of PPV and derivatives, see: (a) McDonald, R. N.; Campbell, T. W. J. Am. Chem. Soc. 1960, 82, 4669. (b) Wessling, R. A.; Zimmerman, R. G. U.S. Patents 3, 401, 152, 1968; 3, 404,132, 1968; 3, 532,643, 1970; 3, 706,677, 1972. (c) Wessling, R. A. J. Polym. Sci., Polym. Symp. 1985, 72, 55. (d) Gagnon, D. R.; Capistran, J. D.; Karasz, F. E.; Lenz, R. W.; Antoun, S. Polymer 1987, 28, 567. (e) Heitz, W.; Brügging, W.; Freund, L.; Gailberger, M.; Greiner, A.; Jung, G.; Kampschulte, U.; Niessner, N.; Osan, F.; Schmidt, H.-W.; Wicker, M. Makromol. Chem. 1988, 189, 119. (f) Lenz, R. W.; Han, C.-C.; Stenger-Smith, J.; Karasz, F. E. J. Polym. Sci., Polym. Chem. Ed. 1988, 26, 3241. (g) Momii, T.; Tokito, S.; Tsutsui, T.; Saito, S. Chem. Lett. 1988, 1201. (h) Tokito, S.; Smith, P.; Heeger, A. J. Polymer 1991, 32, 464. (i) Burn, P. L.; Bradley, D. D. C.; Friend, R. H.; Halliday, D. A.; Holmes, A. B.; Jackson, R. W.; Kraft, A. J. Chem. Soc., Perkin Trans, 1 1992, 3225. (j) Conticello, V. P.; Gin, D. L.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 9708. (k) Hilberer, A.; Brouwer, H.-J.; van der Scheer, B.-J.; Wildeman, J.; Hadziioannou, G. Macromolecules 1995, 28, 4525.
16. For examples of PPV and derivatives, see: (a) McDonald, R. N.; Campbell, T. W. J. Am. Chem. Soc. 1960, 82, 4669. (b) Wessling, R. A.; Zimmerman, R. G. U.S. Patents 3, 401, 152, 1968; 3, 404,132, 1968; 3, 532,643, 1970; 3, 706,677, 1972. (c) Wessling, R. A. J. Polym. Sci., Polym. Symp. 1985, 72, 55. (d) Gagnon, D. R.; Capistran, J. D.; Karasz, F. E.; Lenz, R. W.; Antoun, S. Polymer 1987, 28, 567. (e) Heitz, W.; Brügging, W.; Freund, L.; Gailberger, M.; Greiner, A.; Jung, G.; Kampschulte, U.; Niessner, N.; Osan, F.; Schmidt, H.-W.; Wicker, M. Makromol. Chem. 1988, 189, 119. (f) Lenz, R. W.; Han, C.-C.; Stenger-Smith, J.; Karasz, F. E. J. Polym. Sci., Polym. Chem. Ed. 1988, 26, 3241. (g) Momii, T.; Tokito, S.; Tsutsui, T.; Saito, S. Chem. Lett. 1988, 1201. (h) Tokito, S.; Smith, P.; Heeger, A. J. Polymer 1991, 32, 464. (i) Burn, P. L.; Bradley, D. D. C.; Friend, R. H.; Halliday, D. A.; Holmes, A. B.; Jackson, R. W.; Kraft, A. J. Chem. Soc., Perkin Trans, 1 1992, 3225. (j) Conticello, V. P.; Gin, D. L.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 9708. (k) Hilberer, A.; Brouwer, H.-J.; van der Scheer, B.-J.; Wildeman, J.; Hadziioannou, G. Macromolecules 1995, 28, 4525.
17. For examples of PPV and derivatives, see: (a) McDonald, R. N.; Campbell, T. W. J. Am. Chem. Soc. 1960, 82, 4669. (b) Wessling, R. A.; Zimmerman, R. G. U.S. Patents 3, 401, 152, 1968; 3, 404,132, 1968; 3, 532,643, 1970; 3, 706,677, 1972. (c) Wessling, R. A. J. Polym. Sci., Polym. Symp. 1985, 72, 55. (d) Gagnon, D. R.; Capistran, J. D.; Karasz, F. E.; Lenz, R. W.; Antoun, S. Polymer 1987, 28, 567. (e) Heitz, W.; Brügging, W.; Freund, L.; Gailberger, M.; Greiner, A.; Jung, G.; Kampschulte, U.; Niessner, N.; Osan, F.; Schmidt, H.-W.; Wicker, M. Makromol. Chem. 1988, 189, 119. (f) Lenz, R. W.; Han, C.-C.; Stenger-Smith, J.; Karasz, F. E. J. Polym. Sci., Polym. Chem. Ed. 1988, 26, 3241. (g) Momii, T.; Tokito, S.; Tsutsui, T.; Saito, S. Chem. Lett. 1988, 1201. (h) Tokito, S.; Smith, P.; Heeger, A. J. Polymer 1991, 32, 464. (i) Burn, P. L.; Bradley, D. D. C.; Friend, R. H.; Halliday, D. A.; Holmes, A. B.; Jackson, R. W.; Kraft, A. J. Chem. Soc., Perkin Trans, 1 1992, 3225. (j) Conticello, V. P.; Gin, D. L.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 9708. (k) Hilberer, A.; Brouwer, H.-J.; van der Scheer, B.-J.; Wildeman, J.; Hadziioannou, G. Macromolecules 1995, 28, 4525.
18. For examples of PPV and derivatives, see: (a) McDonald, R. N.; Campbell, T. W. J. Am. Chem. Soc. 1960, 82, 4669. (b) Wessling, R. A.; Zimmerman, R. G. U.S. Patents 3, 401, 152, 1968; 3, 404,132, 1968; 3, 532,643, 1970; 3, 706,677, 1972. (c) Wessling, R. A. J. Polym. Sci., Polym. Symp. 1985, 72, 55. (d) Gagnon, D. R.; Capistran, J. D.; Karasz, F. E.; Lenz, R. W.; Antoun, S. Polymer 1987, 28, 567. (e) Heitz, W.; Brügging, W.; Freund, L.; Gailberger, M.; Greiner, A.; Jung, G.; Kampschulte, U.; Niessner, N.; Osan, F.; Schmidt, H.-W.; Wicker, M. Makromol. Chem. 1988, 189, 119. (f) Lenz, R. W.; Han, C.-C.; Stenger-Smith, J.; Karasz, F. E. J. Polym. Sci., Polym. Chem. Ed. 1988, 26, 3241. (g) Momii, T.; Tokito, S.; Tsutsui, T.; Saito, S. Chem. Lett. 1988, 1201. (h) Tokito, S.; Smith, P.; Heeger, A. J. Polymer 1991, 32, 464. (i) Burn, P. L.; Bradley, D. D. C.; Friend, R. H.; Halliday, D. A.; Holmes, A. B.; Jackson, R. W.; Kraft, A. J. Chem. Soc., Perkin Trans, 1 1992, 3225. (j) Conticello, V. P.; Gin, D. L.; Grubbs, R. H. J. Am. Chem. Soc. 1992, 114, 9708. (k) Hilberer, A.; Brouwer, H.-J.; van der Scheer, B.-J.; Wildeman, J.; Hadziioannou, G. Macromolecules 1995, 28, 4525.
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21. For examples of PPE and derivatives, see: (a) Sanechika, K.; Yamamoto, T.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1984, 57, 752. (b) Trumbo, D. L.; Marvel, C. S. J. Polym. Sci., Polym. Chem., Ed. 1986, 24, 2311. (c) Tateishi, M.; Nishihara, H.; Aramaki, K. Chem. Lett. 1987, 1727. (d) Giesa, R.; Schulz, R. C. Makromol. Chem. 1990, 191, 857. (e) Moroni, M.; Le Moigne, J.; Luzzati, S. Macromolecules 1994, 27, 562. (f) Solomin, V. A.; Heitz, W. Macromol. Chem. Phys. 1994, 195, 303. (g) Yamamoto, T.; Yamada, W.; Takagi, M.; Kizu, K.; Maruyama, T.; Ooba, N.; Tomaru, S.; Kurihara, T.; Kaino, T.; Kubota, K. Macromolecules 1994, 27, 6620. (h) Ofer, D.; Swager, T. M.; Wrighton, M. S. Chem. Mater. 1995, 7, 418.
22. For examples of PPE and derivatives, see: (a) Sanechika, K.; Yamamoto, T.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1984, 57, 752. (b) Trumbo, D. L.; Marvel, C. S. J. Polym. Sci., Polym. Chem., Ed. 1986, 24, 2311. (c) Tateishi, M.; Nishihara, H.; Aramaki, K. Chem. Lett. 1987, 1727. (d) Giesa, R.; Schulz, R. C. Makromol. Chem. 1990, 191, 857. (e) Moroni, M.; Le Moigne, J.; Luzzati, S. Macromolecules 1994, 27, 562. (f) Solomin, V. A.; Heitz, W. Macromol. Chem. Phys. 1994, 195, 303. (g) Yamamoto, T.; Yamada, W.; Takagi, M.; Kizu, K.; Maruyama, T.; Ooba, N.; Tomaru, S.; Kurihara, T.; Kaino, T.; Kubota, K. Macromolecules 1994, 27, 6620. (h) Ofer, D.; Swager, T. M.; Wrighton, M. S. Chem. Mater. 1995, 7, 418.
23. For examples of PPE and derivatives, see: (a) Sanechika, K.; Yamamoto, T.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1984, 57, 752. (b) Trumbo, D. L.; Marvel, C. S. J. Polym. Sci., Polym. Chem., Ed. 1986, 24, 2311. (c) Tateishi, M.; Nishihara, H.; Aramaki, K. Chem. Lett. 1987, 1727. (d) Giesa, R.; Schulz, R. C. Makromol. Chem. 1990, 191, 857. (e) Moroni, M.; Le Moigne, J.; Luzzati, S. Macromolecules 1994, 27, 562. (f) Solomin, V. A.; Heitz, W. Macromol. Chem. Phys. 1994, 195, 303. (g) Yamamoto, T.; Yamada, W.; Takagi, M.; Kizu, K.; Maruyama, T.; Ooba, N.; Tomaru, S.; Kurihara, T.; Kaino, T.; Kubota, K. Macromolecules 1994, 27, 6620. (h) Ofer, D.; Swager, T. M.; Wrighton, M. S. Chem. Mater. 1995, 7, 418.
24. For examples of PPE and derivatives, see: (a) Sanechika, K.; Yamamoto, T.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1984, 57, 752. (b) Trumbo, D. L.; Marvel, C. S. J. Polym. Sci., Polym. Chem., Ed. 1986, 24, 2311. (c) Tateishi, M.; Nishihara, H.; Aramaki, K. Chem. Lett. 1987, 1727. (d) Giesa, R.; Schulz, R. C. Makromol. Chem. 1990, 191, 857. (e) Moroni, M.; Le Moigne, J.; Luzzati, S. Macromolecules 1994, 27, 562. (f) Solomin, V. A.; Heitz, W. Macromol. Chem. Phys. 1994, 195, 303. (g) Yamamoto, T.; Yamada, W.; Takagi, M.; Kizu, K.; Maruyama, T.; Ooba, N.; Tomaru, S.; Kurihara, T.; Kaino, T.; Kubota, K. Macromolecules 1994, 27, 6620. (h) Ofer, D.; Swager, T. M.; Wrighton, M. S. Chem. Mater. 1995, 7, 418.
25. For examples of PPE and derivatives, see: (a) Sanechika, K.; Yamamoto, T.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1984, 57, 752. (b) Trumbo, D. L.; Marvel, C. S. J. Polym. Sci., Polym. Chem., Ed. 1986, 24, 2311. (c) Tateishi, M.; Nishihara, H.; Aramaki, K. Chem. Lett. 1987, 1727. (d) Giesa, R.; Schulz, R. C. Makromol. Chem. 1990, 191, 857. (e) Moroni, M.; Le Moigne, J.; Luzzati, S. Macromolecules 1994, 27, 562. (f) Solomin, V. A.; Heitz, W. Macromol. Chem. Phys. 1994, 195, 303. (g) Yamamoto, T.; Yamada, W.; Takagi, M.; Kizu, K.; Maruyama, T.; Ooba, N.; Tomaru, S.; Kurihara, T.; Kaino, T.; Kubota, K. Macromolecules 1994, 27, 6620. (h) Ofer, D.; Swager, T. M.; Wrighton, M. S. Chem. Mater. 1995, 7, 418.
26. For examples of PPE and derivatives, see: (a) Sanechika, K.; Yamamoto, T.; Yamamoto, A. Bull. Chem. Soc. Jpn. 1984, 57, 752. (b) Trumbo, D. L.; Marvel, C. S. J. Polym. Sci., Polym. Chem., Ed. 1986, 24, 2311. (c) Tateishi, M.; Nishihara, H.; Aramaki, K. Chem. Lett. 1987, 1727. (d) Giesa, R.; Schulz, R. C. Makromol. Chem. 1990, 191, 857. (e) Moroni, M.; Le Moigne, J.; Luzzati, S. Macromolecules 1994, 27, 562. (f) Solomin, V. A.; Heitz, W. Macromol. Chem. Phys. 1994, 195, 303. (g) Yamamoto, T.; Yamada, W.; Takagi, M.; Kizu, K.; Maruyama, T.; Ooba, N.; Tomaru, S.; Kurihara, T.; Kaino, T.; Kubota, K. Macromolecules 1994, 27, 6620. (h) Ofer, D.; Swager, T. M.; Wrighton, M. S. Chem. Mater. 1995, 7, 418.
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135. See refs 1b-e and: (a) Rehahn, M.; Schlütter, A.-D.; Wegner, G.; Feast, W. J. Polymer 1989, 30, 1060. (b) Fahnenstich, U.; Koch, K.-H.; Müllen, K. Makromol. Chem., Rapid Commun. 1989, 10, 563. (c) Kim, Y. H.; Webster, O. W. J. Am. Chem. Soc. 1990, 112, 4592. (d) Rehahn, M.; Schlütter, A.-D.; Wegner, G. Makromol. Chem. 1990, 191, 1991. (e) Cramer, E.; Percec, V. J. Polym. Sci., Polym. Chem. Ed. 1990, 28, 3029. (f) Rehahn, M.; Schlütter, A.-D.; Wegner, G. Makromol. Chem., Rapid Commun. 1990, 11, 535. (g) Scherf, U.; Müllen, K. Makromol. Chem., Rapid Commun. 1991, 11, 489. (h) Reference 15a. (i) Martina, S.; Schlütter, A.-D. Macromolecules 1992, 25, 3607. (j) Helmer-Metzmann, F.; Rehahn, M.; Schmitz, L.; Ballauff, M.; Wegner, G. Makromol. Chem. 1992, 193, 1847. (k) Scherf, U.; Müllen, K. Polymer 1992, 33, 2443. (l) Scherf, U.; Müllen, K. Macromolecules 1992, 25, 3546. (m) Lambda, J. J. S.; Tour, J. M. J. Am. Chem. Soc. 1993, 115, 4935. (n) Witteler, H.; Lieser, G.; Wegner, G.; Schulze, M. Makromol. Chem., Rapid Commun. 1993, 14, 471. (o) Rau, I. U.; Rehahn, M. Makromol. Chem. 1993, 194, 2225. (p) Goldfinger, M. B.; Swager, T. M. J. Am. Chem. Soc. 1994, 116, 7895. (q) Lambda, J. J. S.; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11723. (r) Reference 15b. (s) Reference 15c. (t) Vahlenkamp, T.; Wegner, G. Macromol. Chem. Phys. 1994, 195, 1933. (u) Huber, J.; Scherf, U. Macromol. Rapid Commun. 1994, 15, 897. (v) Claussen, W.; Schulte, N.; Schlütter, A.-D. Macromol. Rapid Commun. 1995, 16, 89. (w) Hu, Q.-S.; Vitharana, D.; Liu, G.; Jain, V.; Pu, L. Macromolecules 1996, 25, 5075. (x) Reference 1 g.
136. See refs 1b-e and: (a) Rehahn, M.; Schlütter, A.-D.; Wegner, G.; Feast, W. J. Polymer 1989, 30, 1060. (b) Fahnenstich, U.; Koch, K.-H.; Müllen, K. Makromol. Chem., Rapid Commun. 1989, 10, 563. (c) Kim, Y. H.; Webster, O. W. J. Am. Chem. Soc. 1990, 112, 4592. (d) Rehahn, M.; Schlütter, A.-D.; Wegner, G. Makromol. Chem. 1990, 191, 1991. (e) Cramer, E.; Percec, V. J. Polym. Sci., Polym. Chem. Ed. 1990, 28, 3029. (f) Rehahn, M.; Schlütter, A.-D.; Wegner, G. Makromol. Chem., Rapid Commun. 1990, 11, 535. (g) Scherf, U.; Müllen, K. Makromol. Chem., Rapid Commun. 1991, 11, 489. (h) Reference 15a. (i) Martina, S.; Schlütter, A.-D. Macromolecules 1992, 25, 3607. (j) Helmer-Metzmann, F.; Rehahn, M.; Schmitz, L.; Ballauff, M.; Wegner, G. Makromol. Chem. 1992, 193, 1847. (k) Scherf, U.; Müllen, K. Polymer 1992, 33, 2443. (l) Scherf, U.; Müllen, K. Macromolecules 1992, 25, 3546. (m) Lambda, J. J. S.; Tour, J. M. J. Am. Chem. Soc. 1993, 115, 4935. (n) Witteler, H.; Lieser, G.; Wegner, G.; Schulze, M. Makromol. Chem., Rapid Commun. 1993, 14, 471. (o) Rau, I. U.; Rehahn, M. Makromol. Chem. 1993, 194, 2225. (p) Goldfinger, M. B.; Swager, T. M. J. Am. Chem. Soc. 1994, 116, 7895. (q) Lambda, J. J. S.; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11723. (r) Reference 15b. (s) Reference 15c. (t) Vahlenkamp, T.; Wegner, G. Macromol. Chem. Phys. 1994, 195, 1933. (u) Huber, J.; Scherf, U. Macromol. Rapid Commun. 1994, 15, 897. (v) Claussen, W.; Schulte, N.; Schlütter, A.-D. Macromol. Rapid Commun. 1995, 16, 89. (w) Hu, Q.-S.; Vitharana, D.; Liu, G.; Jain, V.; Pu, L. Macromolecules 1996, 25, 5075. (x) Reference 1 g.
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144. See refs 1b-e and: (a) Rehahn, M.; Schlütter, A.-D.; Wegner, G.; Feast, W. J. Polymer 1989, 30, 1060. (b) Fahnenstich, U.; Koch, K.-H.; Müllen, K. Makromol. Chem., Rapid Commun. 1989, 10, 563. (c) Kim, Y. H.; Webster, O. W. J. Am. Chem. Soc. 1990, 112, 4592. (d) Rehahn, M.; Schlütter, A.-D.; Wegner, G. Makromol. Chem. 1990, 191, 1991. (e) Cramer, E.; Percec, V. J. Polym. Sci., Polym. Chem. Ed. 1990, 28, 3029. (f) Rehahn, M.; Schlütter, A.-D.; Wegner, G. Makromol. Chem., Rapid Commun. 1990, 11, 535. (g) Scherf, U.; Müllen, K. Makromol. Chem., Rapid Commun. 1991, 11, 489. (h) Reference 15a. (i) Martina, S.; Schlütter, A.-D. Macromolecules 1992, 25, 3607. (j) Helmer-Metzmann, F.; Rehahn, M.; Schmitz, L.; Ballauff, M.; Wegner, G. Makromol. Chem. 1992, 193, 1847. (k) Scherf, U.; Müllen, K. Polymer 1992, 33, 2443. (l) Scherf, U.; Müllen, K. Macromolecules 1992, 25, 3546. (m) Lambda, J. J. S.; Tour, J. M. J. Am. Chem. Soc. 1993, 115, 4935. (n) Witteler, H.; Lieser, G.; Wegner, G.; Schulze, M. Makromol. Chem., Rapid Commun. 1993, 14, 471. (o) Rau, I. U.; Rehahn, M. Makromol. Chem. 1993, 194, 2225. (p) Goldfinger, M. B.; Swager, T. M. J. Am. Chem. Soc. 1994, 116, 7895. (q) Lambda, J. J. S.; Tour, J. M. J. Am. Chem. Soc. 1994, 116, 11723. (r) Reference 15b. (s) Reference 15c. (t) Vahlenkamp, T.; Wegner, G. Macromol. Chem. Phys. 1994, 195, 1933. (u) Huber, J.; Scherf, U. Macromol. Rapid Commun. 1994, 15, 897. (v) Claussen, W.; Schulte, N.; Schlütter, A.-D. Macromol. Rapid Commun. 1995, 16, 89. (w) Hu, Q.-S.; Vitharana, D.; Liu, G.; Jain, V.; Pu, L. Macromolecules 1996, 25, 5075. (x) Reference 1 g.
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158. π-stacking interactions between biphenylene segments of polymer chains have been theorized to provide sites for crystallization: (a) Rogers, H. G.; Gaudiana, R. A.; Hollinsed, W. C.; Kalyanaraman, P. S.; Manello, S. S.; McGowan, C.; Minns, R. A.; Sahatjian, R. Macromolecules 1985, 18, 1058. (b) So, Y.-H.; Zaleski, J. M.; Murlick, C.; Ellaboudy, A. Macromolecules 1996, 29, 2783. (c) Reference 22w.
159. π-stacking interactions between biphenylene segments of polymer chains have been theorized to provide sites for crystallization: (a) Rogers, H. G.; Gaudiana, R. A.; Hollinsed, W. C.; Kalyanaraman, P. S.; Manello, S. S.; McGowan, C.; Minns, R. A.; Sahatjian, R. Macromolecules 1985, 18, 1058. (b) So, Y.-H.; Zaleski, J. M.; Murlick, C.; Ellaboudy, A. Macromolecules 1996, 29, 2783. (c) Reference 22w.
160. This strategy of placing 2 and 2′ substituents on biphenylene segments to minimize π-stacking interractions has been applied toward reducing the crystallinity of polyamides. See ref 27a.
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